Jon Rineman is the first to admit that he rubbed people the wrong way during his nine years working on Late Night with Jimmy Fallon and The Tonight Show Starring Jimmy Fallon. Still, it came as a shock to him when he was told that he’d have to work from home if he wanted to continue writing for the show.
In part three of his candid three-part sit down Mark Malkoff, Rineman tells the story of how his dream job slipped between his fingers.
He also shares how he ended up writing the Seth Meyers joke that some believe led Donald Trump to run for president, and recalls the time he accidentally knocked Lorne Michaels to the ground. You’re going to want to buckle up for this one, it’s a wild ride.
Earlier this year Rineman published his first-ever book, The Garden is Always Greener, an alternate NBA timeline of the Boston Celtics. It’s available at Amazon and wherever books are sold.
Click the embed below to listen now, or find Inside Late Night on Apple Podcasts, Spotify, or wherever you listen to podcasts.
Visit Jon Rineman’s official site and follow him on Instagram and Twitter/X.
Show Transcript
Mark Malkoff: Jon Rineman. Thanks for coming back.
Jon Rineman: Thanks for having me, Mark.
Okay. So you are at dinner with Amy [Ozols] and she is, is she the head writer? Is that, or the producer?
She is now going to be the head writer. So when Miles…
This is at Fallon’s Tonight Show.
Fallon’s Tonight Show. So there was some turnover, personnel changes in the fall of 2016, where Josh Lieb left the show and then Deetch, Mike DiCenzo, that’s his nickname is Deetch.
And then Jim Bell came in?
No, this was before Jim Bell. So this was…
Oh, before Jim Bell. Okay. Please continue.
So this is, uh, Mike DiCenzo, Gerard Bradford, Katie Hockmeyer, uh, all become like a three headed showrunner. I don’t know. I truthfully don’t know what… I’ve only heard rumors. And, you know, as, as Bruce says, you know, I don’t subscribe to rumor and innuendo. So for me, it’s hearsay and scuttlebutt. I, I don’t know about that, but something went on where somehow Miles was unhappy or someone was unhappy with him. I, I truthfully don’t know because I was, you know me, I was always buried in the jokes in my own head, uh, listening to the same music every morning to get myself ready. Uh, an insane person just sitting there writing jokes about Chris Christie being fat, and hardly spending any of the money. You know, it’s just all that mattered to me was being the best at that thing. So I don’t know what was said or whatever, but some kind of falling out went on, I think. And then Miles ended up leaving the show, uh, in early 2017. And even before he left, he phased out of being head writer and then was kind of more of a backstage producer for the last, I think, 2 or 3 months when he was there and we butted heads during that time because I felt like he was taking his anger out on me. I let loose all the. anger, I’d had towards him for years just because I resented having someone we all resent having someone in front of us at first when you work for someone like Jimmy and there’s a Miles there to be sort of the the filter, everyone resents the filter.That’s such a difficult job to have.
It’s a hard thing to do
Because everyone thinks Jimmy is such a nice guy. Jimmy and I always get along when we see each other at the holiday party. Jimmy and I always riff and have a good time in the meeting. I bet if I had Miles’s job and I was dealing with Jimmy, I could do it better because I bet I’m smarter than him and things wouldn’t be so hard. Because we don’t know what it’s like, we don’t know how hot the sun can get until you’re flying near the sun. So, we butted heads and regretfully didn’t even really talk. We did have one kind of sweet moment in Florida. We, the last week that Miles was working there as a producer was in Orlando, we went and did a week of shows down there and he and I happened to be leaving the hotel at the same time, walk over the park. And we had a really good, like 15 minute conversation, kind of just catching up on not speaking really for the last three or four or five months while he was deciding to leave the show. And we’ve spoken since then, and I let him know how much I appreciate him. He changed my life. He believed in me. He defended me. I don’t think anyone defended me more than A.D. Miles at that show, and I just didn’t appreciate it and didn’t really know it at the time. But long story short, he’s gone completely by April 2017. On April 10th, my daughter’s born on April 17th. I’m in the Miles chair. I’m the guy that goes in the green room. I’m the guy that runs rehearsal. I’m the guy that’s taking bullets, so to speak, because Jonathan Adler, he, it’s not his personality. He didn’t really want to do it. Arthur Meyer, uh, no, he’s more of a, he’s pacifist more so than… I’m the one that’s like, you gotta speak up. And so I didn’t, like I said, it was just me and Jimmy and God, it was, it was tough for the first two months. It really, really was tough.
Why?
The reason it was tough is because I had a new baby at home, and a wife that needed help taking care of that baby, and I wasn’t doing a good enough job on that end.
And you were not sleeping? You were three to four hours of sleep?
No, but I was projecting, but I was projecting on, yes, Jimmy was difficult, but I was, I was blaming all my problems on him. I was, when I would talk to Deetch and Gerard, I would complain and make it out to be like Jimmy’s fault. Like, Jimmy’s too difficult. Jimmy’s too hard on jokes or whatever. Fact of the matter is, I was not being a good husband. I was an absentee father, and I was taking out, you know, aggression had, and at both ends, the aggression was coming out. The work aggression was coming out at home. The home aggression was coming out at work and I was blaming all my problems on, like, you know, one or two people being difficult. When I needed to get my sh*t together and so finally we get to a place where Jimmy and I, we had, if we finally had a fight, we had, and it was on email. So I still have it. And I laugh at it sometimes because it’s too passive aggressive Catholics, uh, trying to have an argument and it’s really, you know, it’s, it’s like, uh, it’s of course it’s on email because we’re not going to say it to each other’s face.
What was it about?
It was about, there was a day that Patti Harrison was on and she was there to do a correspondent bit when Trump said he didn’t want transgender people in the military. And it was very last minute. Patti didn’t have any time to write this bit. I mean, we all know Patti Harris. If you give Patti Harrison four hours notice, she can come up with something great. But this was, I think they gave her like an hour, like to have rehearsal ready. So that means she’s got to go in to get a wardrobe. She’s got to get hair and makeup. She’s got to figure out some, like what she’s going to say. So, Deetch comes into my office and says, You know, Hey, we need a few jokes for Patti for her correspondent bit, or it’s not going to be long enough. Can you give us your three best or four best jokes from the monologue on this story? So it’s one of the rare times in my life where I’m a team player and I say, sure. Whereas, the smarter thing would have been saying, Deetch, these are the only jokes I got, you know? But I said, sure, thinking someone might cover for me and explain it to Jimmy. Okay, well that doesn’t happen. And we go into rehearsal and we have one sh*tty joke, one straight monologue joke, on this story, and it bombs. And then Jimmy’s looking at me, and tears me up. It was the one time, the one time he really yelled at me, was that day. The one time, folks, if you’re listening, and he was furious, and he said, biggest goddamn story out there, and you don’t, you don’t have one joke on it, and no one speaks up, no one says this is what happened, so I take, I take the hit.
Can I just interject real quick?
Sure.
Almost every late night host has been like this with the writer at some point. I mean i’ve known people that worked at all of them. This does. Oh, yeah happen. Their name is on the show Please continue.
Well, I will I will respectfully say I have heard from people that Jay was never like this
Oh, yeah.Yeah. Yeah. Jay is jay.
He’s the unicorn.
Yeah, but I will we’ll say that that this was Fallon did not yell a lot. It wasn’t a yeller. This was just Was it, this was an isolated.
He would, he, well, like I said, he would yell at you in print, um, sort of that way. And so it was up to you how you wanted to interpret it. You could, you could be offended, which I was sort of at first, or you can say, what is he saying to me here? Not how is he saying it? What is he asking for? And just get to the meat of what he’s asking for. But the one, but the one time, you know, there’s these stories that go around about, like, him yelling. I got yelled at one time in nine years, in nine years. Well, well, two times if you count the time the kickball went through my legs when we were playing the daily show at kickball, I got yelled out a little bit for that. I got called Bill Buckner and I deserved it.
I got the reference.
But the one time, the one time I got, I really got reamed on this day. So, but I felt it was unfair. So I sent him an email. So I want, I just want you to know what happened today. And I explained the whole thing about I had jokes for you. These were the three jokes. Patti’s, they all killed, they were supposed to be monologue jokes, you know, blah, blah, blah. And we went back and forth. It was like an eight email exchange over the course of an hour. And the next day, Kelly comes in and she goes, hey, Jimmy’s not going to read jokes anymore in the morning.
This is Kelly Powers, Jimmy’s assistant.
Jimmy’s now producer, yeah.
Producer, yes, now producer.
Jimmy’s not going to read jokes anymore and I’m like, Alright, who’s it going to be? Because I’m thinking I’m getting demoted or whatever. And she goes, You are. And I go, What do you mean? And she goes, And then I email Jimmy and I go, What is going on here? And he goes, You’re gonna pick every single joke. I’m gonna let you pick every single thing you want. Everything you want rehearsed, I will rehearse. It’s all up to you. Let’s try it out.
That’s a lot of pressure.
We killed that day. We walked away from rehearsal with like 28, 29 jokes when he only needed 15. We did it again the next day, we killed. It was good and bad. It’s where I fell back in love with the show. It’s where I earned Jimmy’s respect. It’s where I sort of became the, the champion, so to speak. Like if we’re going to use a wrestling term, I was the one wearing the belt at that point of all the writers, uh, because you know, Rineman’s the one that, you know, look at Rineman. He’s, he’s got it all figured out. Like every day, it’s great. But I became even more of an absentee father. I became even more of a… Because I wanted to keep that streak going. I wanted to be like undefeated. And so that’s how it was for much of 2017. And we had, I’m damn proud of the work we did. We had some really strong monologues. We were up against it. Uh, we were losing for the first time to Colbert, but we started to crawl up. We started winning the demo again. Our monologue, as Gerard pointed out to me, went from an average length of. And this isn’t miles as fault. This is just because. There was all this turmoil going on, but towards the end of his regime, Gerard said, we’re doing about three minutes of mono. That was it. That was the average mono was three minutes under me and Adler, Jonathan Adler was doing the sketch bits that would go in the mono. But the mono is now seven minutes. So we had grown the mono. Lorne was happy with it. Everyone. We were getting quick and I started to feel like we might come back. And Jimmy’s mom died. And that was such a to this day, you know, that’s a genuine moment, obviously. I mean, like I remember when Jimmy had, especially with my dad being sick and knowing that I was gonna have to face it soon, Jimmy having to give that on air tribute to his mom. That’s one of the most, that’s probably the most courageous thing I’ve ever seen someone doing comedy. That was an unbelievable moment. I wanted to run out there and say, stop this sh*t, like, you know, let this guy grieve. But he did it and he took him a couple of takes, but he nailed that and still was ready to go. Like what jokes do we have? Like the next day, like he was such a gamer. Then all of a sudden, after it seems like we’ve, you know, we’re cohesive and everyone’s getting stuff on from the monologue and we have a system, no one knows the personal problems I’m having because I haven’t shared them with anyone yet. They didn’t know that my wife and I were sleeping in different rooms for several months. They didn’t know that I was going to a neurologist because I had TMJ and migraines and I was dizzy before the stroke and everything.
You were only eating, like a meal a day, a meal and a half, and you’re doing like nine coffees and you could not take three to four hours of sleep a night. You’re not taking care of yourself.
Right. Yeah, I was, it was, yeah, I was really. I had abused myself and I was, yeah, I was taking, uh, supplements, shall we call it, to stay awake and, uh, you know, and be funny and everything in addition to the coffee and all that stuff, uh, not cocaine or anything like that, but like, you know, maybe going to one doctor and going to another doctor and the doctors didn’t know about each other, that sort of thing. Yeah, that was going on. Then Amy’s back all of a sudden, and she’s back and she’s saying, why don’t you quit? And this is when I’m like, man, this is when I thought I just figured this out, like we’re getting ready to buy a house, you know? So what happened was, finally in February, there’s only so much, and I, I, there’s a lot I can’t say, but what I can say is, in February we were not seeing eye to eye, Amy and I, uh, there were a couple incidents where we really had it out with each other. And it was all very surprising to me because like I said, I thought Amy and I got along, I thought we were friends. She came to my wedding, she gave me a gift. Uh, we wrote a pilot together. But I was not in her plans. There was just something about, she had just decided that I was not part of the program. And so at the same time, this was going on, my dad had Alzheimer’s and the medicine he’d been taking for Alzheimer’s stopped working. There’s about a two year period that the medicine he was on works, and we hit two years and all of a sudden he couldn’t remember which was right and left and he couldn’t drive anymore. And so that was going on. Um, I was starting to get sort of the scary ultimatums, uh, from Rebecca and some people were trying to help out and saying, dude, I think this is serious here, man. I don’t think she’s fooling around. And also I felt like all I can describe it is that every day it felt like I’d hit my head. There was one day where, I still remember this. I was so tired. That it, it felt like in one eye, it was nighttime and I was going to sleep and then the other eye was morning and Rebecca was putting the baby down to, you know, try to wake me up, you know, cause I, I was with Sadie in the morning before I went to work, so that Rebecca could do errands and do some things and stuff. And I didn’t know, I couldn’t, I like honestly didn’t know if it was nighttime or daytime. I was so tired. And so I went in and said to someone there who is in power, uh, that, hey, this is what’s going on. And I, you know, we had talked for a while about, cause I did not take paternity leave, that maybe someday I could do with some people have done at the show. They had taken a hiatus. Uh, Arthur Meyer went and, uh, did a TV pilot for a little while. So he left the show for a bit and he came back a conquering hero. Albertina Rizzo went and did a movie. She wrote on a movie for a bit in Toronto, I believe. And she got to come back. It was fine. People had been doing it and I’m looking at it. I’m like, all right, well, Amy, you got your head writer, and you got your people and everyone’s doing great. And you know who the story is going to be, you know, it’s going to be Trump. So maybe now’s the time to do it. So there was some reluctance and they finally agreed. And then they said, Hey, at the last minute, one change here. Uh, you need to write from home, though. And I’m like, what do you mean? I go, that’s not the deal. The deal is that I’m going to go away for a bit, like six weeks. You can have my salary. You can freeze my contract and everything, and my non-compete and everything. All that, I’ll give you the money, I just need to go away. No, for you to keep your job, we need you to keep writing from home. So, it’s a totally pointless thing. It’s totally point… like I might as well just kept going to the office, but by now it’s already official, that I’m gonna be taking time away. So, I’m away from the office, and all I have to do is write jokes. I don’t have to read anyone’s stuff. I don’t have to organize the mono or the stories or anything. I don’t even have to watch the news. I just got to see what we’re being asked to write about and just write jokes. I’m murdering. Mark, I’m getting like 20 jokes a week, like for the first time. And you’re like, I’m just cause I had nothing else to do and I’m just sitting there, but at the same time, my baby’s crawling up and I’m picking her up like she’s a cat and giving her back to my wife. I can’t, I’m writing my jokes, you know? It’s totally pointless that I’m home. It’s worse. Like, I might as well be in the office. Like, it’s stupid that I’m home, you know, doing any of this. On top of that, I’m not there, right? Amy is, and the monologues are great because they’re getting four or five jokes a day that they weren’t getting before, from me, who do you think looks good in that scenario? The guy who’s not there? Or the new head writer that’s there to say, yeah, we really killed it today. Of course she looks good. So I start to realize this a little bit too late that I think I screwed myself a little bit here. Like, I think I thought that I was going to leave, and that she was going to flounder, and uh, I was going to come back in again and be undefeated and never have any problem in the office. So I get a call on a Thursday that… uh, from the person that said I could take the leave and they say, Hey, so you’re not going to come back. And I go, am I fired? Cause like we had talked a lot about it and they go, no, we’re going to pick up your option, but we’re going to take away your title and you’re just going to write jokes, and you can’t come into the office anymore. And I say, what did I do? And I, you know, and they go, this is, you know, this is what Amy wants. And to their credit, they were not pleased with it. Like there was some hesitancy and there was some, “I’m sorry to have to tell you this” to it. And some “I don’t necessarily agree with this” to it, but that was it. And I sat on it for a couple of days. And then I talked to this person again and I said, you know, I really want to come back. Like, I think we can make this work. We set a time tentatively to talk like maybe a week after that fact. But what the ultimate moment for me that I wish had not happened, uh, was there was one night where I decided to go into the office and get something…get a picture of me and Sadie that I wanted to make sure I had. So I could set it up on my desk, wherever I’m going to be. Like, I guess we’re, I don’t know if I’m going to be in the office. I don’t know what’s going on, but I wanted to make sure I had this picture and I go into 30 Rock. And I go into my office and all my stuff is gone. They packed up my desk. They packed up my pictures, a snow globe, a mouse pad. It’s all gone. And someone else has moved in to that desk. And at no point had they said, we’re doing this. At no point had they called and asked my permission. And I lost it. And it was like, you know, in my world, it was like walking in on your girlfriend cheating on you or your wife cheating on you. There was a board with photos of all the writers and you see this board, and your picture for the first time in nine years, isn’t there? It’s not there. Yeah. And Adler was. You know, I mean, he still had his job. He’s, and I think it just, his picture now just said head monologue writer, not co-head monologue writer, whereas we each had made sure it said co-head monologue writer before. And I wish I hadn’t done that. I wish I hadn’t gone in that night because if I had, I don’t know when it was done. I don’t know whose decision it was to do it. I did get an, you know, an apology from someone there, but never from any of the people close to that decision. So I don’t know what happened, but all I know is I left to get myself. I left, I for once did the right thing and said, I’m going to step away from a possible argument. I’m going to step away from a conflict. I don’t know why Amy doesn’t want me here, but I didn’t think about, but in the moment you’re always living, and just as a monologue writer, you’re living day to day. You’re living current. And you don’t stop and think about all the times you were rude to people. When you were first starting out, you don’t think about all the times you rub people the wrong way and didn’t apologize for it. In your head you’re thinking, God, this past year and a half, I’ve been on the best behavior. I’ve been respectful. I’ve done a good job. No, one’s going to know that there’s no, like, I mean, now there’s, you know, LateNighter. Maybe you guys would write, like, “Rineman’s no longer an assh*le.” Um, but there was, back then, there was nothing where people could say, “oh, this guy’s actually really turned his life around and he’s really got a different attitude.” She had all that baggage to play with and just in that moment, I knew it was all over, you know, and I just thought of all the years I put into the job and how much I, and I like everything flashed like in that moment as I’m looking around the office, trying to figure out like, where’s all my stuff? And then when it finally hits me, I’m thinking about that interview when I walked in wearing this jacket and tie. Thinking about going to Kinko’s and sending jokes into Jay. And I’m thinking about telling Rebecca. I got the job and it’s just all of a sudden it’s gone and. I lost it. I, I, I had a breakdown at that moment where I had, that was the first time I had a panic attack.
In 30 Rock?
Uh, I got the hell out of it. As soon as I figured out what was going on, I, I, I power walked out of there like a, like a scene from a movie or something, you know, where someone catches someone cheating or someone realizes they’ve been cheating. You know, they did a bad investment or one of those dramatic Act Two scenes. I just walked down to the subway and, uh, on the subway and on the path train, I just had a massive panic attack because all I could think was, you know, you’re someone who used to write for Jimmy Fallon now, like, you know, it’s like, they don’t want you back. You know, you were thinking you could talk sweet talk your way back into the office and have things be the way they were, and maybe get along with Amy [Ozols]. Clearly, that all your stuff is gone, and your pictures down.You’re out of sight, out of mind, and the people in charge have stopped fighting for you, and they don’t want you back. And look, man, if I had to do over again. At the time I had management, I had a agent and a manager, and I just said, you guys take care of this. Like you guys get me out of this deal and whatever. That was f*cking stupid, not what I should have done.
What should you have done?
I should have contacted Deetch and Gerard directly and said, Hey, I don’t like that this happened. And for me to like, I need to talk to Jimmy. Like that would have been my thing. Or I might, or I would have tried any way I could to talk to Jimmy. That’s what I should have done to begin with. I mean, like I should have, out of respect, I didn’t want to go over anyone’s head, but when things were getting untenable and I was not feeling well and things were not going well.
You did not know that you had a mini stroke for a long time. I mean, this was, was it for a whole year that you didn’t know that you had a mini stroke or close to that?
Two years. And it was, I had a lot of, a lot of issues, but I thought they were all, I thought I had a mental breakdown. I mean, I did. But I thought it was all mental and it wasn’t until two years later that, uh, but by then it was, you know, past the, the time that they can really find out what happened to you that, but they were just, they found some evidence and all that. And it runs in the family on my mom’s side. So it made sense. But I should have just said. I should have grabbed Jimmy one day in the green, in the cue card room, and just said, Hey, can I talk to you for a minute? And I should have just said, I got to go away. You know, like, I, I’m not feeling well. And I know that knowing Jimmy that had he known if I had said to him, Rebecca and I were having trouble, that would have been enough. And I think he would have said, go do what you have to do. But. I played cute, and I played egotistical, and I thought I could outsmart Amy, just like I seemingly outsmarted everyone else, but you’re out of sight, out of mind. What I should have done after I found an office like that, I should have, Uh, especially nowadays when you’re older, you know, like now that I’m older and I have more perspective, I’ve worked other places, you know, I’ve had other jobs since then, and I’ve never had any moment that heavy, but I’ve had other moments where I found out I was getting screwed or I found out someone was lying to me or I found out someone was just crazy, you know, and I had to deal with them and I just took, took a deep breath. That’s from going to therapy. You know, you, you reframe it. You, you compartmentalize when you can. Sometimes I’ll just, I’ll go for a walk. I’ll go for a mile walk. I’ll think, all right, how are we going to figure this out? And you come back and you keep doing the job. And I think if I were mature then, like I was now, I would have said that’s a real sh*tty thing you guys did. But it’s pretty irresponsible as someone with a wife and child to just walk away from a job this great. So where do we go from here? It might have been like, you know, like, can I just get an apology for that? And can we just kind of talk this through? Because Mark, there are, there are many times there are two or three times that I almost went back to the show. One time in 2019 where I had an interview went so far where Jim Bell called me up, and we had like a phone interview about me coming back and it was about me re-proving myself and all that. But then in the two days between I was supposed to be getting my deal on a Thursday night. And our phone call was on a Tuesday morning, that Thursday, a big hit piece about Jim Bell came out.
That was the New York Post?
Yeah, Page Six. And the deal was off. Like, he was basically like, I, you know, I, I don’t really have the pull right now to justify bringing you in with all this history and everything. And, um, but I was, I was supposed to come back. Like, had that story not come out, I probably would have been back at the show. And I really wish I had because, you know, I was in such a good place at that point. I had been through therapy. I had just taught at Emerson, which reinvigorated me and, and I was really good at writing again, but… Again, like I tell people, if you’re a jerk to people earlier in your career, and you’re snarky and you’re not mature, uh, that adds up, and look, there are some people who have been that way and waltzed right back on in to the Fallon show. You know, they were given a second or sometimes third or sometimes fourth chance and whenever they need a gig, they get it back. Again to use the wrestling analogy. I’m more on the Randy Savage or CM Punk side of things, where it’s like, yeah, he’s the guy that’s not coming back. Like, you know, I know CM Punk did, so I can’t use that analogy anymore, but Vince was gone. You know what I’m saying? Like it was like, it was a, it’s a different regime. And so it’s like. There’s just that thing and I get, you know, it’s funny. I’ll have, I hear from interns and stuff. I get messages through my website and they’ll be like, “Hey, I just interned at Fallon and you know, I heard all these things about you and they’re like, what happened?” You know, and I never really tell them if I don’t want to, like, bottom down with all that, but they always say like, why can’t you go back, you know? And I’m just like, well, a lot’s gone on since then. But I mean, really, I would say until about 2021, even though I’ve been gone, I was still pretty loyal to that show. Like it really is when it’s like with anybody, it’s like, when you start hearing rumors about yourself, like the rumors on my end were that I got in a physical fight with Jimmy, that never happened. There was a rumor that I cheated on my wife with an assistant. Never happened. There were rumors that I had said or done certain things to Amy that never happened. And so at that point to defend your character, especially when it’s costing you jobs, other jobs in the business and in life, you got to defend yourself. And I know they don’t love me telling this story. I’m not saying anything disparaging about them. I’m just telling exactly what happened. But yeah, it’s like, all I know is, Jimmy and I ran into each other in 2022 at a comedy festival. And it was when I was doing morning radio and he agreed to do an interview for my show and we did it right there and man, it was like no time had passed at all. It was just so funny and he was so great and we were just ribbing each other just like we would in a writer’s meeting, and he was that dark kind of funny, you know, like he was at the off the cuff, honest Jimmy funny, but that was the last time I heard from him. And, um, you know, that was, uh, that was it.
You mentioned in your AMA, from I think that was 2020 in November, that you were on a podcast and you, you said these are, I believe your words, that you took a, a cheap shot, a joke at Jimmy’s expense.
Yeah.
I, I listened to that podcast interview, uh, today. Did that joke get. To Jimmy that you, you said..
I heard it did, and I heard he didn’t appreciate it. And I think that was where, that’s where things started to go south, and…
Did you apologize? Did you feel like you had to apologize?
I did when he took a shot at me subtly in the show.
Oh. What was the shot? How could you tell?
He did the Rineman impression. He did the, “er” character and then made a little comment after the fact that I was like, oh, you know, that was, that was a pitch. He threw that pitch over my head, you know, like,
Were you watching the show or did you hear about it?
I was watching it. I was watching it because I thought he did the best at home shows of anybody during the COVID lockdown to the point where I emailed Gavin and said, man, maybe you guys should just do this. Like, I was like, maybe just quit the Tonight Show. Do the Jimmy Fallon show. Let Mulaney or I guess it’s before it’s, you know, that was a bad choice. It’s before John went through all his stuff, um, and conquered all the things he had to conquer. But I just said, maybe let Mulaney or someone, whoever. Amber, take a, you know, I’ll just let them get the Tonight Show. Let’s do it. You do this at home show with Jimmy’s great and I’m watching the show one night and there I’m like, oh, there’s the ramen impression. And there were a couple other things like that that felt very subtle, personal. I knew him well enough to know, like, oh, this, you know, this, this came up then where, you know, things really kind of fell out was They were just doing a ton of dementia jokes in the monologue. Like every joke about Biden or Trump was just an Alzheimer’s joke. And I had emailed without success a couple of people there to just say like, Hey, you know, is there any way you could, you know, These jokes are kind of hurtful towards, you know, it’s like, I think there’s other angles for Donald Trump that you can take other than making fun of disabled people. And this is why I’m, this is why I’m saying this to you. So you understand, you know, it’s, it’s, it is a subjective thing for me. And then he just doubled down and he did even more. And, uh, I don’t know if that was him. I don’t know if that was a head monologue writer or whatever. Immaturely. I took it personally because when you have a narcissistic personality, which I was born with, and I’ve had to fight through therapy and all sorts of things in life experiences past few years to kind of beat, you think you’re always the star of the movie. And so, you know, if you’re watching a monologue one time, and there’s 3 straight jokes, and one is about. Unemployed people. The next one’s about single dads and the next one’s a dementia joke, you’re the crazy person. You’re Charles Manson hearing your name and Helter Skelter. You know what I mean? And so that was just my immaturity, but yeah, but there was other things too. Like it was just like certain people were promoted. Certain people were brought back that I thought had dicey reputations just like me and I just felt I felt left out. It felt unfair, you know, especially when they knew how bad I wanted to come back. And so that was it, you know, and that was kind of our the last, you know,
But he did agree to come back and do an interview with you, which was…
He did. Yeah, it was great. Were you surprised? He came over to me. I thought, you know, we had there had been some business stuff. Like there is when anyone leaves a show, there’s some business stuff that has to be settled. And like, when anyone leaves a show, it gets, you know, contentious and cantankerous or whatever you want to call it. He, I did not want him to have to be really a part of it, but of course he was. And I thought he was going to blow right by me. I was like, this is a guy that I have some not so nice recent history with from a business standpoint, not from a personal standpoint, not from a, you know, if you read that AMA. Uh, there’s a lot of questions I skip and there’s a lot of stuff that I maneuver out of respect because, you know, it’s none of people’s effing business at certain times, or because I genuinely just don’t know, which is probably the case in a lot of situations. I, you know, what’s he like when he goes… Well, I don’t know, man, I was at home writing my jokes every night, you know, so I had plausible deniability, but he came up to me and gave me the biggest hug possible. Uh, then we kind of looked at each other again, like, Oh my, you know, Oh my God, are we doing this? And he gave me another big hug and it was awesome, man. It was, it was such a cool thing. And
That says a lot about him. It really does.
I mean, it does, but it’s like, I wish, I wish we were able to maintain a friendship beyond that just because I feel like. Like I said, in nine years, we had one fight, we had one real fight and we made up, you know, we figured out that it wasn’t really the, we’d each kind of been left in the dark about certain things. It was just about a monologue joke. And other than that, it was great. He was great to me. And when it’s left to just me and him to figure things out, it’s fine. Now, look, man, I, I don’t have any eyes on going back to the Tonight Show and on any, any designs on going back to late night, I think I’m healthier without it. I think the TV that I’m producing now is healthier and it’s more rewarding in many ways, but it’s a shame that like when something happens, like when there’s a Beach Boys thing in the news or there’s a wrestling thing in the news, it’s a bummer to not be able to email Jimmy, you know, what do you think about this and make jokes and just kind of go back and forth for a few minutes, you know? It’s a bummer that. When he comes to New Hampshire, and he’s just a couple hours away from me, uh, in Massachusetts, New Hampshire, wherever I happen to be at the time that we can’t just hang out and, you know, because I come from, we’ve talked a lot about this, the other times I was on. For all his faults and holy sh*t are there many, but you know, one thing, one good thing, if you’re going to say good, any good thing about Vince McMahon was his attitude of never say never. And his attitude that with the exception of Randy, and we don’t know why, I guess I’m Randy in this situation, people are allowed to either come back or maybe we can partner up and work on something else. Dude, it’d be great to f*cking get with him and work on something else, you know? Even if it was, I would do a whole show about me being an asshole writer, you know, I mean, that was in the air for a little while with Alec Baldwin, that was after I did stand up one time, uh, he kind of caught wind of who I was. And that’s always been kind of an interesting premise and I don’t mind it. Like, I don’t mind burying myself and talking about, you know, where I f*cked up and all that stuff, but at the same time, man, I, like you talk about, yeah, I’ve taken shots, I’ve made my jokes, you know, I’ve made jokes about Jimmy, I’ve made little quips, but that was me projecting and taking out my anger about my life and my own mistakes on him.
And so it’s like, There, there gets to a point where you realize, yeah, I’m not divorced because of Jimmy Fallon. You know, I’m not sick because of Jimmy Fallon or I’m not, you know, Uh, trying to find my way in the world because of this. I, it’s like, no, it’s because of you. It’s because of who you are. And since I took on that responsibility, and took accountability for all that stuff, I would say it started about 10 or 11 months ago, the end of 2023 is when I really stood up and started saying, what do I need to do to make things right with certain people that anger went away.
That’s fantastic.
And so if any, if any, if anyone from the show is listening and boy, I bet they are, um, you know, I apologize. I apologize for, you know, I know it’s been a difficult time for them. And I know that at times I’ve poured gasoline on that fire and I know it got real old. I know at first, maybe it was a little bit cute that Rineman was out of the woodwork and talking some smack and defending himself, but it’s been tough for them. I know I empowered other people to run with it. I’ve been quoted certain places, both in and out of context. Uh, when people were trying to make him look bad and that was just me being immature. I apologize. God knows what’s going to happen and life throws you curveballs. And so, you know, for all I know, I hope it’s not this way. I really hope it’s not this way. But six months from now we could be not talking again. But when I apologized to Rebecca for the way I’d been as a husband, uh, and bringing work home and, and all that, and she accepted the apology, that was a life changing moment for me. Like that really, it was like, holy sh*t, it was like, and then doing stuff, the three of us as a family again, and then even getting coffee, just the two of us, it’s like, that f*cking seemed impossible just a year ago. Like, that was like, God, that’s no way that will ever happen. You know, it was almost like, you know, we were told by lawyers not to let it happen, you know, like, stay away from each other, you know, don’t give anyone anything to work with. That was a real wake up call for me. And when I started approaching life that way, and taking responsibility for what I can control. You know, I already thought I had gotten through all that when I had rebounded and had other jobs and done other things, I thought I was “okay.” I thought I had lived it. But when you’re still having work dreams about a place, you don’t work. You got to sort that sh*t out. You know, you got to talk to people and
I have, I’m not going to mention the show, but I still have bad dreams and it’s like they haven’t happened in maybe about a month, but I was having at least, um, it was really to, to a week from a place and I can’t, and I still have it. I still have issues. I can’t, it’s been hard to let go. I want, I really want to. I want to.
No, I had, I just had one the other day. I had a, I had a dream that I think I was trying to get the rehearsal monologue or something organized and Oh, that was another thing is, uh, towards the end we were on a Google Doc and it, dude, it was ridiculous. It was like. Amy and I were both in there at the same time trying to edit the same thing. And it was like, it was so, so Larry Sanders, dude, it was so, it was such a, like, you don’t, you know, like me trying to type it before she can delete it. And then I see it, the cursor come up and go, ah, you know, just like, like it. But I had a dream about that the other night that I still had that nightmare. And I woke up. And it was just like, oh, I was like, no, dude, you’re, you’re about to start, about to start working on another TV thing. You’re, you’re getting your masters. It’s like, things are good with Rebecca. Just chill. You know,
That’s great. What TV thing are you doing? If you can talk about it.
I can’t really talk about it yet, but it’s a more, it’s definitely in the more. Brighter side of the road sort of realm.
I’m happy to hear that.
And it’s produced producing, which I’m super excited about, which I’ve never really gotten to do and do some remotes and do some stuff like that. And, you know, we’ll see how it goes. I mean, like I said, for, you know, for all I know, they might go and say, man, you’re too comedy for this, you know, but I’m really, really looking forward to it and very grateful. You know, learning that new skill, so to speak, so.
That’s fantastic. I do have a couple of follow up questions. The first thing is when you had that dinner with Amy, was it later that night that you had the mini stroke on the same night?
Yeah, and I didn’t realize that until like two years later. Like I was going back. I did this thing in therapy. It’s called EMDR therapy. And it’s when you’re almost hypnotized, you follow this little blinking cursor across your computer screen or or whatever, or if you’re in the office, they have these like clickers or so it makes you have like, like REM sleep, but you’re awake. So you’re, you’re basically in the moment again. And that’s when the whole passing out on the train incident came back. And I remembered the night, cause I remembered that Rebecca and Sadie were up in Massachusetts. They weren’t home. I came home by myself and I put things together and then I went on my email and found eight email drafts to Adler that night. And like five of them said the same thing. Like it was like me forgetting I’d started to write an email, you know? They’re all just like, it was like, Hey, for tomorrow. And it was like different wording of the same idea and never sent. Like, it was like, I kept clicking out and starting it. Like, I don’t know what I was doing when I first got home. Don’t remember much of that night. And then I somehow found the email from Amy about like, Hey, let’s meet at Bill’s Burgers. And I saw the date and I went, Holy shit. That’s the day. Like it was January 8th. It was that Monday night. It just goes to show you that if you’re, cause I wasn’t that like, I was disappointed that she didn’t want me around. I was disappointed that she had other questions and stuff that stays between me and her. Nothing inappropriate, just stuff about the show and different ideas that I found questionable personally, but I wasn’t like panicked. Like I wasn’t freaking out. It’s just everything boiled over that night. It was just a matter of, I do remember I didn’t really eat my dinner. Like I, I’d gotten, it was Bill’s Burgers. So I got a burger. And, uh, I had like half of it, which is very unusual for me. I usually eat the whole thing, but I didn’t have much of an appetite after I had been asked to leave the show. I was like, huh, I don’t know about that. And then from not eating and then the stress and the being tired. And I do remember that day I did not feel well at work. I do remember thinking to myself, man for having two weeks off for Christmas. And having a really good break and having a really nice time with Rebecca and seeing friends and going to Celtics games, I feel like sh*t, like, I remember feeling that day I was talking to Steven Levinson is one of the writers. And I was like, I just feel like, cause he had a big day that he had some good jokes. I was like, man, it’s good to get some stuff. Cause I had, I had nothing today. You know, I was just flat for some reason, but it was just, I tell people now, I’m like, if you’re not feeling well. And things are off. You got to do a check. You got to do the check engine.
When did the WWE, the four of you, when you went to ringside, when was that after or before the Amy dinner?
That was two weeks later. That was Monday, the 22nd of 2018. And by that point, Jimmy wasn’t really, yeah, he wasn’t really talking. I remember the three of us were waiting for Gerard in the cue card room to go. And we were eating McDonald’s or something. And. I remember me, Amy and Jimmy sat and I was thinking to myself, God, it’s weird that we went five minutes and no one talked. Like, I was like, that’s never happened. We wrote a pilot, the three of us together, you know, this is really weird. But again, I didn’t, I, I wasn’t really piecing things together to at that point, so.
Can you tell us the story about how you almost injured Lorne Michaels?
Yeah, sure. Um. One day there was a day, well, I did injure Lorne Michaels. There was a day where, I would read cue cards. So I would sit in the back with Steve King and Roman Urbanski or whoever it happened to be at the time. And I would read the cards, I would proof them. And then. Um, once they were all done, I’d hand them to Steve or Roman and they’d walk them into the cue card room and then Jimmy would read them with Miles, there. This is before I’m in the cue card room. Cause miles is still the show. And one day we had a couple of late jokes. I think there was like a late-breaking story or something and I had to bring them in mid read. So Jimmy was already, and that happened every now and then. And he was always cool about it and everything. And I brought them. You know, I’d bring them in and here you go, whatever. So one day I go there and I go knock on the door. I always knocked on the door cause I knew it was a heavy door. No answer and I just burst in like Kramer because I’m trying to get these cue cards in, and then, Just like you hear the loud poof of like a hard door at a TV studio hitting something and then, like the thud on the floor and I look around the room and I see cue card guy. I see Gavin. I see Miles. I see there’s Jimmy. There’s Leeb There’s Hockmeyer. There’s Higgins Oh, shit. There’s one person that I don’t see, and then I hear from in front of me, Oh! Oh! Oh! Oh! Oh! Oh! Oh! Oh! Oh! Oh! Oh! Oh! Oh! Oh! Oh! Oh! and I look, and Lorne is, like, head-first on the carpet. He’s like, he’s trying to get up, but like, his head is still down. Like he’s that far, like you know when you’re trying to push yourself up, but you’re… and I look around the room and dude, I just f*cking ran. I ran. I hear Oh!, and then Higgins kind of stood up for me. He goes, “Well, you’re right in front of the door!” And I just dropped the cards and I run. And I go back to my desk and I sat there. I think I stayed till 7 PM just cause I was like, if I’m going to get fired, like I’ll take it, you know, I’ll take it like a man, nothing happens. And I just go into Miles’s office and I’m like, hey! And he goes, you’re not fired. Like, that was all he said. And I went, okay, good.
What a relief!
Yeah. Yeah. Yeah. It was like he, and then, uh, he’s like, he was blocking the door, like, don’t worry about it. But like, dude, I hit him right on the elbow, like, right. And I could feel for that too, cause I hate when people bump my elbow, man, that kills me. And so like, but, uh, yeah, knocked him over. But they got me back years later and they cleaned out my office. No, I’m kidding. I’m kidding.
You did stand up twice on Fallon. And I do want to mention you started in Boston, Rick Jenkins, right?
Comedy studio. Yeah.
You were at the comedy studio. Rick was, uh, Rick Jenkins has been very supportive of the Carson podcast and myself, and, um, so you got to do the show. Uh, Fallon show you did the 12:30 show, which I know you mentioned went really, really well. And then you did The Tonight Show where it was a little bit more challenging. There were more restrictions that were placed. Is that true?
They both went, they both ended up going really well.
Oh, good.
And, and I think that there were better jokes in the Tonight Show set, but. The late night set was just, again, it was Disneyland. Like that whole 12:30 show. I didn’t know how good I had it, you know, like none of us did. Like that was just such a dream job and a dream show. Gosh, that was so much fun. The tonight show set, it all felt like it happened so quick to like getting the set, getting it ready, getting it on, like being out there, standing there with The Roots on one side and Jason Sudeikis. I, like I showed my daughter, I was like, see, I did stand up in front of Ted Lasso. You know, like it was very impressive. It was. It just felt so cool. like being on a roller coaster. The tiny show felt like dragging a boulder. Like it was really, it was, I found out so early that I was going to be doing it like too early that there was too much time to craft the set and it, it felt like a drag and I got tired of rehearsing it and I got tired of running it and. There’s different rules, like, in Late Night, I make a joke about Kohl’s. On The Tonight Show, you can’t mention any brands. Anything that has to do with brands. Like, I wanted to do a thing about having Skechers shoes. Nope, you’re not, not allowed to do that. So, okay, I can’t do that one. The funniest story from The Tonight Show set was, I had a pretty innocuous joke about Pope Francis. And it was about, he was such a nice Pope, I think he was trying to get fired from Pope. Like, I think he was just being, he was like, Oh, you want to get divorced? Go for it. You know, like it was just like he’s doing on that. Everyone’s had that joke and angle ever since. But I was kind of the first, catholic.I was sort of there and I get called in joshley and he says, you got to cut your pope joke. And I go, you’re kidding me because it was my closer and he goes, I go, why? And I go, because it’s religious? People are going to get upset? And he goes, no. Uh, he’s like, we might have the pope on the show. And we almost did. That’s how big Fallon. That’s how big the Tonight Show was, was that he was a 50/50 guest when he was visiting New York and there he’s going to be in the studio and everything. And so it’s like when I make that, I actually, I think I actually said to Josh, what is the pope coming on the show? And he goes, Yeah, maybe. I’m like, what? And he goes, it’s, he goes, but even say he goes, this is the Tonight Show. It’s like, it’s, it’s, it’s awesome that you’re doing this, but there are a lot of rules now that, you know, you, you can’t, you know, and he’s like, I went through your Late Night. He’s like the mannequin joke. You probably couldn’t do that, like, you know, on, on the 1130 show. Yeah, it’s, but also the, you know, the thing I regret about that set was. It was so personal. It was so autobiographical and whereas the late night set was very observational and very evergreen and it’s just everyone can have fun. Whereas the Tonight Show said it was a lot about like, maybe I should have asked my parents, if I should do this joke, maybe I should have asked Rebecca if I could do this. And, you know, this friend, maybe I should have run it by. And there was too much, it got a little too, a little too raw. So I liked the 12:30 set a lot more and a shout out to, uh, Mark Liepis, who, uh, great producer who produced that 12:30 set and made some really good calls and some good some good advice stuff to leave good advice on things to cut
I do want to mention, with him. I don’t know him, but the one thing I really liked about the 12:30 I don’t know if I if I want to say I like it, but I thought it was very very interesting is he was a former publicist, correct?
Mm hmm. Yeah, still still does some publicity. Yeah.
And Mike Shoemaker’s rule, I don’t know if that he did that with Jimmy, is is that we’re not going to get anybody on the 12:30 show that has ever worked in late night. I mean, they were adamant about that, correct?
Yeah, that was right. I think the only person that had worked in late night was Morgan Murphy and she had worked, she worked for Kimmel. But Miles got to hire one writer when he was made head writer to see the way the way they did that too was they put together the writing staff first and then they picked the head writer. So that’s kind of always how they’ve done things at that show, and sometimes it works sometimes it doesn’t but I know that when Miles got hired it’s my understanding that he said can I bring Morgan Murphy with me just have at least one person smart worked out pretty well I would say she’s done some pretty good things so.Yeah.
Then, is it two years in? I don’t know if I have the year right. Was it 2011 that Mike Shoemaker says, how would you like to write a few jokes for my friend’s big dinner? Was that 2011?
Yeah. Yeah. For my friend Seth’s dinner.
Okay. So. And you do not know that this is going to be Seth Meyers or the Correspondent’s dinner at this point.
No. I have no idea. So I’m at work. Uh, one day he just corners me before the monologue meeting. Hey, hey buddy. Hey buddy. You know, Shoemaker. Hey buddy. How you doing? How’d you like to, uh, write some jokes for my, uh, my friend Seth and his dinner, huh? Yeah. Okay, sure. I’ll write some jokes for dinner party. That’s fine. It’s, you know, I don’t even know if I’m getting paid, whatever. So then, uh, yeah, I really want you to, I really want you to meet my friend. But I mean, but you know, he keeps building it up every couple of days. Yeah. Okay, fine. So then, uh, one day he’s like, yeah, he’s going to be in my office. Uh, you know, tell you guys, uh, six o’clock come by and, you know, meet him.
So I go by and I’m with. I noticed that Legdin and Bronson are walking with me. And I’m like, are you guys going to Shoemaker’s office? They’re like, yeah, we’re going to meet Seth Meyers. And that’s when it clicked. And I was like, Oh, Seth Meyers. Still didn’t know it was the Correspondent’s Dinner. I didn’t even know he was, uh, you know, doing the speech or whatever at that thing. So I’m just excited to meet Seth Meyers and talk about the Red Sox with him, you know? Then I find out what this is for. Hey, you’re being, you’re going to be writing for the White House Correspondent’s Dinner. Oh, okay. So we go in on a vacation week, hiatus week, whatever you want to call it. In the room, it’s, it’s Eric Ledgin, it’s Jeremy Bronson, and it’s myself, but there’s also Alex Baze. There’s Neal Brennan. There’s Doug Abeles, there’s John Mulaney, it’s, uh, Mike Drucker is sending stuff in, uh, remotely.
Colin Jost was there too, right?
He wasn’t there! I don’t know why he wasn’t there.
He wrote for it, he did write for somebody,
He was sending, yeah, I didn’t meet him until, until a few months after that. But he, um, he was, it was a murderer’s row. And, I was used to By that point, I was very cocky. So I was, by that point I was either angry or arrogant. That was one of the two A’s and which equal assh*le. So it’s three A’s. And so I was arrogant that week. I was like, Oh man, it’s vacation week. I only have to write two pages or one page of joke, whatever. This is going to be a piece of cake. So we get into the, the read, and I’m last and I’m hearing everyone else’s jokes. And I’m saying, Oh sh*t, cause it’s like John Mulaney. So, you know, it’s John reading his jokes or whatever. So he’s like, you know, Donald, Donald Trump is like a man and then Times Square and he has his children fired people and he’s, you know, all these great things. And I’m like. Oh, I’m like, he just in one joke has more than anything. And I have another one sheet, like that’s just awful. And then, you know, he’s Seth’s reading Baze’s jokes and they’re all, every single one is great. So it gets to my sheet of jokes and everything dies. Like just every joke is just clearly a half wrote it at midnight, watching SportsCenter, already take a sleeping pill joke. So then there’s the very last jokes about it on the page. And it says, Donald Trump says he has been saying he’s going to run for president as a Republican, which is interesting, cause I thought he was running as a prank and I laugh at it myself, which is breaking one of my rules. Like I’m like, ha ha, you know, I’m laughing at my own joke and Seth goes. It’s okay, but is there a better word than prank? And then he’s just like, yeah, he’s about to turn the packet, which would have meant I got nothing on. And I just go, what about joke? What about joke? And then Neal goes, “Yes, joke. That’s it. That’s the word right there.” And Seth goes, “Oh, okay. Yeah, maybe.” So cut to the dinner. And it’s on YouTube now. It’s been viewed however, millions of times. Even my daughter knows this moment. She’s only seven years old. Seth does the joke and Trump is there and he is pissed. A couple of days later, Seth comes down to give me my check for the night. And he says to me, you might want to lay low for a little while. Why? Donald Trump is really pissed at you. Me. You told him? He goes, I didn’t give you up, but he confronted Seth. And he really wanted to know who wrote that joke, calling him a joke. Said that it, it ruined his political career, ruined all this stuff. Now I don’t subscribe to this, but there’s a theory in New York that Seth’s jokes, in particular that one, may have been a, uh, a driving factor in, uh, Mr. Trump pursuing his political ambitions again in 2015 and 2016, you know, in Boston, I know how it got around. I told friends in Boston that I had written that joke and they were cool. They didn’t tell anybody. Everyone kept it quiet. Even my friend at the Globe, you know, waited until I was ready to talk about it, uh, till he heard the story, but he didn’t run with it. And I don’t know how people in New York found out about it, but as that election got closer and closer in 2016, I started hearing, getting texts from people. Like I started hearing from people. It’s like, Hey man, this might be your fault. Cause you wrote that joke. I know it’s not true. But it gets a little annoying after a while. And the night that he finally won, even though it was like 2:30 or 3:30 in the morning, my phone was blowing up. I mean, it was just nonstop texts and it was literally, they all said the same thing from other comics. This is your fault. This is your fault. You did this. You made him do this. This is your fault. And, um, I. I always thought it was just in my head. I always thought it was just me. But the funny thing is, Seth was on the show one time on Jimmy’s show and they talked about that joke and I’m sitting there like, because like no one in the office at that point, they’re all, it’s a different staff. So no one knows that I, and I’m like, don’t give these people ammunition. They’re really funny. You know, it’s Chris Belair. It’s all those guys. And I’m like, please, please don’t. So he gets through, it doesn’t mention it. And then I sent Seth an email and I say. Hey, man, thank you so much for not mentioning that I wrote that joke. And then he goes, he writes back. He goes, I actually forgot. And he showed me his notes for the segment and he wrote Rineman. It had Rineman joke. And I was like, Oh, and I had to go, please don’t anyone, don’t tell anyone. Look, you know, wait till I’m gone. Wait till I’m out of here. But yeah, I will say that as you’re sitting in, as I was sitting in there with Miles every day, putting the monologue together, as the presidential motorcade went by to Trump Tower, that joke didn’t seem so funny anymore.
The Boston Globe did a piece on you and they wrote that you still regret it. Is that, is that true? Or were they being funny?
I think they were, I think they were being, I mean, I know Mark and he’s a great dude and he’s a friend and I thought he did a really good job with that story. I mean, there’s a certain element of entertainment to any piece of journalism. And you know, like I was behind a project at the time that desperately needed some help funding-wise and everything. So I, that’s why I agreed. They were helping me out too, to get my name and we succeeded. We did the thing, but no, I honestly, Mark, I’m more haunted by not helping out the day of the hair tussle. Like I think that I really wish I had written some interview questions that day that were hard hitting and were smart. That was my job, you know? Like that was a, that’s a place I should have been. And look, if, you know, if I get, who knows, man, that election was so close. Who knows? I mean, like, I don’t think it was Jimmy. I don’t think the tussle had anything to do with it, but I think that if Jimmy had one or two really smart questions that he knew a writer like me was behind. So he felt comfortable telling it not that I’m a genius or anything, but just that he knows it’s like, Oh, I know this guy, if he feels good about it, I feel good about it, and maybe he gets Trump. Puts them on the spot a little bit. That interview is a whole different story. It might be Jimmy Fallon asks really insightful question. Jimmy Fallon puts Trump on the spot instead of Jimmy doesn’t ask any question. Well, the fact of the matter is we left Jimmy hanging. We left him high and dry. You know, we, we didn’t give him this. Jimmy was a guy who put me on the show twice. Uh, the second time I was there, he put my parents on the show. He went the extra mile and I couldn’t just write a few interview questions, you know what I mean? Like it was just like, that haunts me a lot more. Like it’s.
There were a bunch of other people in the same situation you mentioned at the show.
Yeah, we all, we all should have done it and I, I feel bad that none of us did, but you know, it’s just like I tell people, go the extra mile with your job, do everything that’s asked of you.
You’ve, you’ve moved forward. I know that you had a really good time teaching at Emerson. I got a kick out of you mentioning that, that none of the students, um, you know, they’ve watched a lot of Seth Meyers, you said they watched John Oliver, but they didn’t know who David Letterman was and you showed them some clips. And they fell in love with Letterman and then you found out over the weekend, yhey’re like, we’re watching Letterman. Did you know he was, he had a show on NBC?
Yeah. Did I know?
I just really got, I really like hearing that.
Yeah. You know what I showed them was the one that really got them was, it was top 10 surprising facts about Sesame Street. It was that top 10 list. The one that killed the most was, uh, after years of speculation, Bert and Ernie confirmed that they are in fact brothers. And the thunderous laugh, like, you know, the, the, the guys, the guys were in for it right away, but like, cause you know, Letterman’s dudes, humor, certain points, but the girls in the class on that joke, the young women in that Emerson class, they were crying, they were laughing so hard. I mean, they like, he won everyone over. Like it was just, it was so amazing to, you know, I think I was 35 or 36 at that time. At that age, after having worked in late night for nine years, it was f*cking amazing to be part of people discovering. The Letterman show. And then, uh, we watched Rupert, the fun with Rupert segment, you know, at the,
Oh, the Jon Beckerman segments where he would, Dave would feed the lines and stuff. And he started that.
Yeah. Yeah. Who, who do you think, who do you think you are? Martha Stewart. Who do you think you are? The Queen of England. You know, he comes back with his thumb and the. Yes. I mean, people. That was, that was the fun. That was so funny. The fun, fun with a cell phone. People were crying. I mean, people were laughing so hard. And, you know, I got to say that it speaks to, in my opinion, I hate to say it, but it speaks to what’s missing in Late Night right now is that there isn’t really, we don’t have that person. We don’t have the person that’s the troublemaker. You know, it just seems like every show is. Like the thing about Dave, I mean, look, another very flawed person and he admits to this and certainly he’s had his skeletons and they’re all out of the closet and, you know, he has accounted for them and God bless. And it’s great. It’s great that we still have him. I love that Dave is. I love watching his YouTube channel and he still makes me, it makes me laugh. Like I’m 12 years old all over again. Never met him. Whenever I meet somebody that knows him, I’m always like, dude, tell me everything about, you know, and it’s cool stuff. But, you know, The thing about Letterman was, it felt like he was, he was an advocate for the underdog. He was fighting from beneath. He would have human interest stories on. I’ll never forget when that guy jumped on the subway tracks and saved somebody. And Dave had them on for, had the guy on for two segments. And it was great.
I think he might have been the last human interest story like that. I mean, they, he was so good. He was very, very good. They had that, that gentleman on and I remember him, um, talk, narrating the clip and…
Then Jay would do that too sometimes Jay had some good human interest people too, and he doesn’t get enough credit for Jay would also put his standups on in the second act. So it would be a guest stand up musical act. So you’d really get… Dave did the same thing sometimes, but I think that. What the students told me and I wrote about this and I got in trouble for it a little bit. Some blow back from I don’t think Katie Hockmeyer is going to be sending me any Christmas cards anytime soon. But again, I don’t have control. I wrote an article that ended up being in Salon magazine. It was originally in The Conversation. It was about. Things I’ve learned from teaching late night at Emerson and things I learned that, you know, the students wish they could see and why they’re not watching late night. And a lot of it linked back to people. I didn’t have control on all the links that were in the story. You know, you know, you know how it works. Mark, when you write something and. You know, Bill Carter could probably tell you this when you write a story in the digital age, and I just had a Celtics column that came out. They control what everything is linked to in the story. You know, so if you mentioned the head of late night, maybe could do this. They’re going to link back to a story about Katie Hockmeyer or whatever. So it looked like I was, you know, but really I was just saying, this is what I’ve learned from all that. And the thing that was a big takeaway from the students, surprisingly. And it makes sense now and you see the rise of TikTok and youtubers and average people so to speak is that they said we’re burned out from all the celebrities were burned out from all the back padding and all these people that are, you know, like the, you know, people that are coming on to promote their skin line when they were just on two weeks ago to promote their sh*tty TV movie or whatever, why don’t they have regular people on? And they actually cited Letterman. They said, I went on letterman and I saw that he had, and I could not, when I saw this, I was like. Who are these kids? They were like, I saw he had Harvey Pekar on and they did these amazing. I was like, how the hell do you know? And they’re like American Splendor, you know? And I was like, Oh yeah,
At 12:30, it is a little bit easier to have those people on. But he was in the beginning of CBS. He was still doing the human interest. And Ellen did that very, very well with the human interest, having them on and having kids on.
Oh yeah, totally.
That did stop though, eventually for Dave, for the most part.
But I would say like, that’s one thing that’s missing is human interest. I think that another thing is that you don’t have, is that the hosts, I mean, Colbert, because as Gerard would say, it’s very cathartic, it’s cathartic to see him come out and bash Trump when that’s how you feel, uh, it’s cathartic for people for had Gutfeld to come out and bash Kamala, if that’s how you feel, you know, I get that, but there isn’t that person that every man or woman that could do it the way [Joan] Rivers did, that could do it the way, Letterman did that makes you feel like they’re with you. You know what I mean? Like, it’s like you watch late night shows. Now the hosts are all, you know, they’re rich, you know, they’re famous, you know, they’re friends with their guests and there’s never going to be an interview. Like if Joaquin Phoenix went on a late night show now, any late night show, and acted like he did with Letterman, you’d never hear about it. Like it would just be edited, it would be cut down to a four minute interview to make him look good because, oh, we want him to come back. I want that guest who’s going to go, No, I’m, I’m not, I’m not dealing with this. I want someone who’s going to stand up to them, I’d love to have it be someone who’s not a white Catholic guy. I’d love to see some diversity in there. But the other thing is, Mark, and people are now catching on to this, and I got in a big fight with somebody that I, I regret to some degree, but, you know, my side of the argument was not totally wrong, which is that YouTube has killed it. I mean, it’s like putting everything on YouTube. The whole segment, for free. Why is anyone going to watch the show? And when people say to me, well, you’re that you got to adjust to the times. You got to live with the times. I’m like, okay, well, you know what? The times are the times are, Seth just had to lay off his band and the tight shows only on four nights a week. That sucks. Those aren’t good times. So you can’t tell me it’s good business to put all your segments on YouTube. The minute the monologue ends, it’s up on YouTube, or in some cases it’s up there two hours before. Who the hell’s going to watch the show? I never watched these shows anymore. And then it gets to the point where you don’t even watch YouTube, you know, it’s like if you’re like, TV was a very habitual thing. Like when I, like when the monologues pop up on my YouTube in the morning, I’ll be honest with you, man, unless I hear from somebody, hey, they did the Rineman impression again, which I think it’s been about a year. I think I texted Miles and called him out on it nicely and said, Hey, I’m, I feel very honored that I’m still a character in the monologue. Um, and I was, but I don’t watch him a lot of times, like I kind of feign my even when I was teaching late night at Emerson, uh, if I didn’t have to watch it, if we were working on. Something different. If we were working on interviews or sketch or whatever, I don’t care. Like I’m just going to skip it. And I think that a lot of people have. And so I think that if it were me, I would say, I think if I were going to pitch a late night show, it wouldn’t be a late night show. It would be you’re on at seven o’clock. You’re on one of the streamers. It’s four nights a week. Let’s take that right up right off the gate. Uh, so it’s Monday through Thursday. You’re on at 7 p. m. live right after the news and that’s it. And that way, because I think that the days of, I hate to say this on a late night podcast, I love late night. I think it has to go away for a while. I think it has to be on at a different time. I think you need to move that up, because think about it, if you’re, You know, like if you’re like me, if you’re, if you’re working and you’re going to school or you have a kid or something’s going on, I don’t want to stay up till 11:30 to hear all the jokes from earlier in the day? You know, I don’t want to stay. I want to hear him right after it happens. If I watch David Muir and I watch the news and or if I watch Lester Holt and I see what’s going on. I want to hear the jokes right after that. That’s the world we live in now. We want immediacy. And so my plan would be, take Jimmy, put him on at 7, or take someone like him, put them on early enough so that, because none of those shows right now are so edgy that kids can’t see them. They’re fine. And then you know what that would do? At a certain point, Gen Alpha, people like my daughter who really like dark and twisted stuff, if you present to them someday after many years of having that show right on, right after the news that mom and dad like to watch. The, you know, the grownup show, like the, the Tonight, Oh, this is the people and the, all the formal people, they talk about politics and stuff and you say, hey, you know, there used to be shows on it, like 11:30, 12:30. That you weren’t supposed to watch that you’d have to sneak from your parents and check it out. You’d have to see it. Really? Then that’s when you get the people like Jeselnik and stuff like that. So my strategy, they’ll never do it. They’re going to keep things the way they are. But I’d love to see Netflix or, you know, somebody like that come in at 7 o’clock with like Leslie Jones and four nights a week. She does the news. She does her thing right after you just saw the news. And that becomes the show that’s the hot show. And then at a certain point, the pendulum will swing. And when little Sadie Rineman is all of a sudden 14 years old, and she wants that blood and guts and gore and foul language, everything. Oh, well, maybe late night, maybe we can bring that back. Maybe we can put some people in there. Maybe pending on what he’s doing. Well, what’s Pete Davidson up to at that point? Would he be interested in doing something that the kids might be in? You remember him from Mr. Beast, right guys? You know, So I think it’s like, I think it’s saveable, but there are issues that need to be dealt with and I hope people do. I hope they think of future generations and, you know, Jay always said he wanted to hand the show off to the next guy. I think Jimmy is probably the same way. I just think that, you know, the YouTube stuff has to stop. It’s like when newspapers would give away their articles for free without a paywall. You’re killing the business. You got to cut back on the YouTube.
Yeah, I don’t know if it’s ever. I don’t think it’s ever going to go back. It’s like saying the WWE is giving away their matches, I think on Mondays, where they can’t do the jobber matches, which they used to do to try to get them into the arenas. Which worked for so long. I know what you’re saying in theory, but I can’t see that happening.
But think about WWE, when did WWE business really in our lifetime? When are times it really took off when it was based in reality, the attitude era for sure. The, so you had the, you had the Montreal screw job and that’s when, uh, Bret Hart found out his office was cleaned out, so to speak, and when he was supposed to win a match and he lost, and then was done with WWE and then, um, Uh, similar reasons didn’t want to do business. So I love Brett, but you know, we could have handled things differently. Maybe I love that. I just put myself in the same sentence as Brett Hart. Anyway, um, but then if you look at when they took off Mark, it was when Vince got kicked out of the company and people were like, Well, let’s see how this is going to go. What are they going to say about it on camera? What’s triple H going to say? Is Stephanie going to stick around? How is this going to play out? And they took control of that moment, as Bruce would say, and made it work for them. And so when, when it comes to late night, when people say to me, it’ll never come back, it can’t come back. That’s the wrong attitude. You need to get out. Hey, look, man, it’s like. I’m happy with what I’m doing now. I’m happy with my life, but you know, I respectfully, if there, if you’re talking to a consultant or someone else that’s thinking broader strokes and they’re telling you, uh, it can never come back to nothing, you do fire that person and give me a call. I’m happy with what I’m doing, but I’d be happy to tell you there are definite ways late night can come back. It has to come back. You need that accountability in the public sphere when someone’s acting like a jack*ss to call them on it and. Make them correct themselves on it. I mean, you know, it’s like, uh, look at Rudy Giuliani. Look at that fall. Just look at, look at how far he’s fallen. People must say like, Oh, he must be humiliated, humiliated by whom? No one’s watching the late night. He’s not watching the shows, making jokes about them. No one watches it anymore. It’s all, you know, it’s like, it’s the YouTube clip we mean to watch and we forget. Whereas if a, if you do like Jay used to do. Jay, who, you know, won for all those years, and take your best three jokes, your best four jokes and make that your YouTube clip. And then at the end of it, it says, “For more watched The Tonight Show every night at 11:30” or “Jimmy Kimmel every night at 11:30” or whatever, or for more close, you know, you put A Closer Look up till halfway to watch the rest of it, go watch it on demand or watch it tonight on 12:30 newspapers did this. They saved the Boston globe that you just mentioned in 2009, the Boston globe was going out of business. They were going to be out of business. There was only going to be the Boston Herald and papers like that made the adjustment and said, sorry folks, but you’re going to have to read this whole article. You’re going to have to log in and to log in, you’re going to have to just pay six bucks a month. Like you would, if you’re getting a new, this is a cheaper newspaper subscription for you, but you got to pay something. And I think you got to do something like that with late night where it’s like, You say, Hey folks, this is a little bit, this is a little bit of the clip that we’re going to show you. You know, here’s the first three jokes from Jimmy Fallon and they all killed, you know, here’s the beginning of the kids, Halloween candy thing with Jimmy Kimmel, and it’s all really funny. We’re going to give you the first third. But to catch a rest, you gotta tune in to the show, and if you don’t, you’re missing out.
It’ll be interesting to see where it goes. I know Michael Che’s experimenting with the late night show. I know that, um, Mulaney apparently is gonna be coming back doing live shows on Netflix.
By the way, I will say, Mulaney, that was as nervous as I’ve ever been to meet anybody, believe it or not, even back in 2011. You just, you just knew with Mulaney, like, I mean, with Jeselnik I was nervous and then Mulaney, yeah, you just knew, you’re like, this guy’s, this guy’s a guy right here.
There was something about him. I was at a, I met him only one time at a Saturday Night Live party when he was just a writer on the show, and he wrote a sketch that I really liked for, for, uh. Bobby Moynihan, he co wrote it. Um, it was the Mice and Men. And I thought that was really, really funny. And I talked to him a little bit, but you could just tell there was just like this charisma and I’d seen his stand up, but he wasn’t famous at all at that point. But he, there was something about him.
His joke about usually drug dealers make people Uh, drug users, but he was a drug user that created a drug dealer. You know, that bit from his last special where he talks about how his drug dealer was trying to get out of the business, but John kept, kept buying drugs. That’s that, that line. Oh my God. That’s just, that was such a great. I mean, it’s coming from such a personal place too, but
He’s such a good host on SNL. He’s he’s phenomenal. I do want to mention your book. I know we’ve talked about it a little bit, um, uh, on some of the other, uh, the two other episodes we did that your book is, uh, the Garden is Always Greener. Um, I know that you were a huge Celtics fan and, you know, it’s, um, really, really funny. You mentioned, was it The Family Guy? A lot of the writers or have been, it’s been going around the writer’s room.
Yeah, it’s been very nice. Yeah. Artie Johann and, um, you know, uh, Alec Sulkin and some of those guys and, um, a few, a few people reached out. Yeah. A few different, then just random people, but yeah, the premise is I, during lockdown when we were all kind of. Stuck inside. Uh, I had a PlayStation five brand new and I had NBA 2k. That was the only game I had kind of did a simulation of if Len Bias had lived and played for the Celtics and saw how everything would have played out, kept a record of it and sat around for a couple of years. And then finally I was like. Boy, I’d really like to write a story around this, like a comedy, something people could have fun reading. So reached out to, uh, Len’s parents and his family and his mom said, God bless. Just, can you use a name other than Len Bias? And I said, absolutely. And it was, you know, I took the win and said, thank you very much. Uh, you know, Dr. Bias and, uh, she was awesome. And, you know, wrote a story that is basically a redo of the nineties. And so it’s got, uh, You know, uh, things happen different, uh, OJ, uh, gets apprehended before anything can go South. Uh, Tupac and Biggie, they got rescued somehow TV shows change or come and go in different ways. And, uh, it’s all sorts of funny stuff with cartoon, uh, fictionalized versions of people like, uh, Shaquille O’Neal and Arvydas Sabonis and Dennis Rodman, and of course, Michael Jordan, who has a much different, uh, arc in this book as well. And it’s sort of like a mix of, uh, Forrest Gump meets a Curb Your Enthusiasm where there’s a lot of running gags and callbacks. And the reason it’s done that way is that, uh, it’s dedicated to my dad who died of Alzheimer’s and, uh, donate from my earnings to, uh, the Alzheimer’s association just made another donation the other day. And, um, it’s cause guys need to read. Um, it’s, there’s a lot of studies that men are of a higher rate of dementia than women and men are not reading and men are not reading fiction and exercising their mind and trying to remember things. So it’s Gardens, The Gardens Always Greener. If you go to gardensgreenerbook.com. You can check it out and read all the rules of the simulation and the history of it and what people have to say. And, uh, yeah, it was a really fun project. And it was also really nice, too, because it’s got a lot of jokes in there. There’s a lot of, like, monologue jokes about each year and things that went on. And there’s a couple fake Top Ten Lists in there and stuff like that. And man, just being realistic. It might be the last time I get to write stuff like that. It was really fun to get to do it in a personal project like this.So gardensgreener book.com. Go check it out.
Jon Rineman. Thank you so much for coming on again. This was fun.
Thanks Mark.
