To hear him tell it, Jon Rineman had the dream job: Writing for Jimmy Fallon—first at Late Night, and then at The Tonight Show. Then it all came crashing down, and he’s got no one to blame for it but himself.
In part two of his very candid three-part sit down Mark Malkoff, Rineman shares stories of some great days working at Fallon, and—in a foreshadowing of what was to come—some not so great days.
Along the way he shares his theory about that classic Tonight Show moment when Nicole Kidman revealed she’d had a crush on Fallon, and why he blames himself for that now-infamous Trump hair tussle.
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 joining us.
Jon Rineman: Thanks for having me, Mark. Happy to be back.
I read an interview with you and you were saying that it was December of the year you were hired. It was, it was Fallon’s first year, a couple months in December of 2009, where you, you really found that the show found its voice, correct?
Yeah, I think it was the Tiger Woods scandal. And I think the, the big reason for that is that, you know, when we were starting the, the challenge was trying to find Jimmy’s voice, trying to find what his stage presence was going to be and what his, you know, values were, you know, because there’s, there’s some theatrics to every comedian’s persona, probably. It was finding out where the characters, so to speak of Jimmy Fallon would come down in certain things and politics. He didn’t really do political stuff. And he admittedly didn’t know about it. So that was hard. Like it always felt like, uh, forcing that through anything with Obama or anybody else. And then he’s not a sports guy. He is a music guy, but he doesn’t want to make fun of anyone in music because you know, they’re, you know, he wants to be friends with them all. He wants them to all come on the show. And then, uh, Tiger Woods was this guy who had just been on, I think right before I got there and everyone felt kind of duped. It was like, he was, Tiger was this guy that always had his wife and his kids run out on the course when he’d win, you know, hug him. And he’d always talked about his family and everything. And it’s like, man, he’s got 125 mistresses. And. I think there was that. I think it was Jeremy Bronson becoming the head monologue writer. That was a good combo for a long time. He and Jimmy, that worked. And it was the holidays, which is always one of my favorite times as a joke writer because there’s so much new material. You know, you gotta, you know, uh, one of my jokes was, you know, well, everyone’s talking about, uh, You know, Dasher and Dancer and Prancer and Vixen, you know, Tiger Woods latest call girls? You know, like stuff like that. And you can pull that out of the box in December, just like you, you can say, what’s a, what’s a Christmas song I can make fun of just like I did. And I think those three things, it just was really freeing. It was like, okay, we found what Jimmy will make fun of, you know, the kind of thing it’s, it’s hypocrisy. It’s maybe someone that’s, it’s not faithful to their family.
You, you were telling me there was an Anthony Jeselnik joke that you really liked. What was it?
Oh, it’s one of my favorites. It was my favorite joke of his, which was, there’s a new set of golf balls and each one has a picture of a Tiger Woods mistress on it. And after inspecting the balls himself, Tiger said, I’d hit that. And that was, you know, perfect. Like we were all just, you know, but then you take that and you can apply it to other stories. You get, you get a little bit of confidence and you say, well, hold on a second. If I can, if I can write that, maybe I can write this political joke. Maybe I can write the sports joke. Maybe I can write this music joke about things that I don’t really know about or whatever. And, uh, our confidence grewBy the, I mean, that Christmas party in 2009. God, dude, it was great. It was, again, it was a dream year. It was like. Everyone was having so much fun. We were rolling and it was just, it was just the dream team. It was me. Uh, like, uh, you know, as I said, last time I was here, I’m like, uh, it was me and the four In Memoriams. It was Jeremy Bronson, Morgan Murphy, Eric Ledgin, Anthony Jeselnik. Somehow, some days I’m getting the most on. It was just amazing. Just a, an amazing time. And, and we all kind of found our roles. Like Eric was really good at sort of the philosophical jokes. Like he would, you know, like, but it’s going to stink when you blah, blah, blah, blah, blah, blah. Like it wasn’t set up punchline with him. It was more like, and Morgan was really good at the act out jokes. Like she’d come up with the back and forth conversation sort of things. Jeselnik, as you know, he was the hatchet man. And Jeremy and I were kind of Pushing each other. We wrote very similar set up, run up punchline, quick quotable jokes. And so there was sort of that friendly rivalry. And so it was the dream team. It was, it was the best monologue team, I think, we had, uh, the whole time I was there. Cause we all did something different and we all pulled for each other. You know, we were all happy when someone got a lot on or when someone got a joke in the New York times or whatever. And I think. Jeselnik had a lot to do with that. Like I said, he was, you didn’t act out when Jeselnik was there because you didn’t want to be on the receiving end of him calling you out for that, which all of us were at some point. And so you, you learn to behave.
Speaking of a dark humor, which Anthony Jeselnik is known for, a lot of comedy people, uh, they have, uh, you know, a really nice persona and I’ve met Jimmy Fallon a bunch of times, really, really nice guy, but I’ve been told by a bunch of people that work there, and I know you’ve said this as well, just much darker sense of humor when the camera’s not on–sarcastic, but really, really funny.
Uh, what I can speak to when I was there, yeah, his dark sense of humor. Especially when he was in a good mood, like when he was in a really good mood and could just freewheel and be dark. Man, he, he was as dark and as pitch black as anybody. And you know, you hear those stories about Conan too, like Brian Kiley always says that Conan behind the I would put Jimmy against Conan.
That’s what I’m told.
People would say that’s insane because you hear Conan on this podcast now, you know, when he goes off the rails and talks about Santa screwing a, uh, birdhouse or whatever, like, like he did when Gary was on, just hilarious stuff. But Jimmy’s mind was so quick and dark. And he had such recall of random things from the past, like the, you know, the McDLT, you know, or baby Jessica, or when just weird random sh*t that he would bring out and some of my best memories there were he and miles in our monologue meetings. Just riffing off each other and Miles was the perfect foil, you know, just go, Oh, really? You know, the straight man, you know, really is that wasn’t Jimmy’s like, Oh yeah, yeah, yeah. And then I, then I ran into, uh, Kato Kaelin, he was there and he, you know, he tells her, Oh yeah, is that right? And just their riffing was the most funny thing. And then my role as I was the time he knew some of the operations, you know, I was the guy, I was the guy that would sit there as the prop, just waiting for Jimmy to make fun of my shirt or making big fun of my haircut or whatever. But the flip side of that was I was able to give it back to him a little bit. Whereas other people didn’t have that license and it was always a little bit scary and the room would kind of gasp a little bit, but he’d, you know, he’d laughed at it, he’d take it, we’d run with it and, um, yeah, his off screen persona when I knew him and he was in a good mood and he was being funny, funniest human being of all time. I mean, just like, there’s like, you’re just, you’d be crying. Like we literally, you know, when people said to me, like, did that show ever make you cry when you worked there? I was like, Yeah, because I was laughing so hard, you know, during the meetings, you know, like is, you know, and well, at what, well, I can’t tell you that, you know, it’s what happens in the green room or what happens in the mono meeting, it stays there and, you know, I can promise you no one was hurt and all that, but it was just, you know, just a bunch of comedy writers, like, let’s talk about all the things we wish we could write about, but we know we can’t, sort of thing, you know.
Speaking of that, you would sneak certain jokes in the monologue that you knew that Jimmy would never do. Try to, you know, be a little bit more edgy. I know that, that you mentioned in an interview where somebody was interviewing you, using an example that Louis C.K. said he would try to get stuff on with Conan a little bit more edgy. And sometimes Jimmy would do it at rehearsal just to amuse the writers or just to amuse, knowing that it would never get in. Is that correct?
Uh, yeah, yeah, he would do, he would do it just to get the monologue laugh. It was usually, we’d put it at the end of the packet, so the monologue, and he would say, that’s just for you, take it home with you, you know, that’s a, you’re not gonna hear that on the show tonight, you know, thanks for coming.
Marshall Brickman, who is the head writer of Carson, tried to get Carson to do edgier stuff as well. I feel like that that’s probably, happens with a lot, with some of the hosts.
Well, I want to, Hey, man, I, you know, not to put myself over too much using another wrestling term, but you know, when I was running mono the last year and a half or so that I was there, Miles was gone or he was there, but no longer really the head writer and, uh, was more working in a producing capacity. You know, I want to take some credit. I got him to do some pretty dark stuff. We did a lot on the Me Too movement. Uh, we did a lot on Harvey Weinstein. Uh, Roy Moore, that guy, the creepy guy that ran down there in the South. Uh, we, we hit him really hard. Uh, I got Jimmy to do two jokes about Charles Manson dying. Uh, and I take that as one of my greatest personal achievement. I wrote one of them. Like that, you know, I, but we were able to put two together that made sense, that felt like Jimmy and you could see in his eyes, there was a little bit of excitement when he went into the setup. Cause it was like, this is, we don’t really do a whole lot of this, but they both worked.
You did an interview. You were talking about that. You were in the cue card room one time or the control room and you were surprised about how much things were scripted that you didn’t think would be scripted. Uh, and you said some of those spontaneous moments you, you wondered in late night, some of those classic moments about that seemed very spontaneous, how scripted they were. What are some examples of some things at Fallon that maybe the audience would be like, Oh, wow, that’s really that that happened. I can’t believe that happened. That was maybe planned.
I still, to this day, think he knew the Nicole Kidman thing was coming. Um, because their mutual friend who I happen to know, I don’t know whatever happened to this guy, but, um, he was a producer at the time. So maybe he’s doing great. And if he is, I apologize, Rick, I just don’t know. I’ve lost such a lot of people, but there was a producer that Jimmy and Nicole each knew and had worked with and he was walking around backstage. So it’s a little bit like a wrestling thing. It’s like the Montreal screwjob a little bit. I’m a skeptic of that to some degree. And I love Bret Hart, but part of me still wonders. Uh, folks, if you go on Wikipedia, Google Montreal screwjob, it won’t get you fired. It’s, it’s a, it’s a wrestling scandal.
I just want to interject. I was literally talking about this with somebody last week that I have so many still questions and I know it’s, it’s amazing that people still talk about it all those years.
As maybe, as maybe we’ll get to, I went through a similar thing myself. But, uh, and, and that was not fake. So I have to respect Bret saying it’s real, but, uh, with, with, with Nicole Kidman, I still think. I, without getting too deep in it, because a lot of it is, you know, a lot of it’s just friendly talk, not locker room talk, like none of that, but a lot of it’s just friendly talk about who we were in college and who we were in high school. And I don’t, Jimmy doesn’t strike me as that. He’s a very perceptive guy. I just can’t believe Nicole Kidman would show up at his apartment and he wouldn’t jump through the roof. Like, oh my God, Nicole Kidman’s here. How can I impress her? So there’s that he said a couple of things that are just telling stories to me about just innocent story. Nothing scandalous, just about just girls, girlfriends he had back in college or just prom date or whatever. I’m like, Jimmy, Jimmy knows is, like, he knows people. And so that conflicts with the person we hear about and then the Nicole Kidman. So that’s a clash. And then their mutual contact. Uh, Rick was there that day walking around and I just, from being in the green room in later years, or the cue card room, I should say, and hearing how things would be planned and how they would come out, and sometimes it’d be my idea. I’d say, why don’t we do it this way and make it look, you know, would this look more real or whatever? I just feel like. 80 percent feel like that was a work. Like he, he knew, I think that, I think he probably found out, he might’ve found out that day, like Rick might’ve gone in and say, Hey, man, Nicole’s here. She’s going to tell this story. And Jimmy might’ve said, are you serious? I always wondered about that. And then, but when they got out on stage with that thing of like, in the moment on TV, Jimmy realized. Now, man, like, I think backstage there was some smartening up that went on there. That’s just, that’s just me.That’s my opinion.
I would imagine with the Taylor Swift, she’s, she’s on the show and then they have this embarrassing video of her, her mom took or something and she’s reacting.
Oh, she knew.
Yeah.
She knew.
That’s what I’m saying.
That stuff. They always know. They always know.
Yeah.
There’s never any. I mean, especially with Jimmy. I mean, even Joaquin Phoenix on David Letterman.
Dave knew.
He blew the gimmick at the end. He stood up and took the glasses off and shook his hand. Yeah.
Dave admitted he knew.
I slapped my bed when I was watching that lie. I said, you just blew it, you fool. Like you just had the most famous segment ever and now it’s only gonna be like an A minus. ’cause you took off the glasses and shook his, like you, you blew the gimmick.
Rosie O’Donnell on her show, which was is, it was an such a huge show at the time, the syndicated show. She had this bit where she would be blindfolded, and there would be this famous person come out, and it would kind of make noises, and she would have to guess who the person was.
Oh yeah, I saw, I saw the Richard Simmons one.
And she revealed that she knew. I mean, that she’s like, I knew, she, this was like in the last couple years, she’s like, I just, I know that, I just, I did know I could make it funnier that way if I knew in advance.
Let me tell you something, I’ll tell you a couple moments, like the Bradley Cooper laughing with the elephant man, that was, that was 100 percent genuine. Like they’re, they were really trying to.
That was great.
They just happened to have those dumb hats and that’s why it’s so great. And you feel that as a comedy writer, like you’re like, that’s real. Like, and I saw it happen live. He really, they, they screwed up. Like they, I think they, in the planning of that segment took something out of the middle or whatever, or maybe kill, or maybe they were supposed to be a commercial or something, but we had so much show, they gave them one big segment. And so there was no chance to take off those crazy visors with the funny hair. And. Bradley really was trying his damnedest to sell that. I mean, we know from the movies he’s done since, he’s a serious, you know, he wants to win the award. He wants to be the serious actor that plays that affects your life. And he really was trying to sell the hell out of that movie. And they really, that was a hundred percent genuine. Um, to my knowledge, when Stevie Wonder popped out of the cake or whatever to saying happy birthday to Jimmy when he turned 40. I don’t think Jimmy knew about that. I think he knew there was a special guest, but I don’t think he knew it was going to be Stevie Wonder, which was fantastic. But, uh, and then the hair tussle with Trump, that was planned. Like that was a, that was a thing going in that it was part of a much bigger stunt, uh, callback wise, that they were going to do with Hillary Clinton. And Hillary said, I don’t want to play ball anymore. So we got caught.
What was the bit that Hillary that was pitched to her?
Uh, she had been coughing a lot and she’d had pneumonia, I think. And there was a rumor that she, uh, might be gravely ill, which was, you know, not accurate, obviously. And so to prove that she was not sick, the bit that was pitched and supposedly approved, although it didn’t happen. Cause I was skeptical. I was like, I don’t know about this. Was that she was going to grab Jimmy by the tie and give him a big kiss on the lips and then kind of push, push him away, you know, push his face away. So, you know, she was going to put on the lipstick and, you know, make sure it’s stuck on his face and everything. So if you’re going to kiss Hillary Clinton, which would have been, I would have loved it just because I hate Bill, you know, I’m a, I’m a liberal leaning person, but I hate Bill Clinton, which you’ll probably, uh, figure out a surmise by reading Garden’s Always Greener. He’s a, uh, routinely made fun of in there. Uh, this book I wrote. But I thought it would’ve been great for Hillary. It would’ve been a great moment that she gets to kiss Jimmy Fallon on the show and everything like that. And I guess to balance that out, because they didn’t want to show bias, they were going to, they did the hair tussle and, uh, you know, I was like, why don’t I mess up his hair? And. Here’s my thing about that. I had, I had nothing to do with the hair tussle. I really didn’t, I didn’t know it was going to happen. I don’t think any of us really knew. We knew about the Hillary bit because we had been told no Bill Clinton jokes, you know, for a week or two or whatever. Be very careful. Uh, be careful with the jokes you make, no sex jokes, whatever. We want to make sure she’d feel comfortable doing this bit. And I think we didn’t even do any jokes like that in the model at all. I think it was like, keep it clean, you know, cause this is a big thing for us. And the tussle would not have been as big a deal if he’d done an interview, if he’d done a real interview with Trump, with some real questions of substance, that hair tussle… instead, he said things like, we’re getting close to the election. How are you feeling? And this is starting to get real. And it ended up just being a softball interview ending with what was supposed to be a blow off. As you say, in wrestling, the blow off from a tense interview was going to be, Hey, we’ve been going at each other. It’s been awkward here for eight minutes. Can I just f*ck up your hair and we’ll make up?
In defense of Fallon, I personally find it completely ridiculous that people think that that was something for him to get all the brunt when he went on Saturday Night Live and he was doing all these other Things I just don’t, and also Colbert admitted people never talk about when he went on, Trump went on Colbert and Stephen even says, he said later, he’s like, I wish I was tough on him. You, I think he has one thing that was a little, that was tough.
But I’ll tell you a story from that day. That is the difference between who I was at that point in my maturity and who someone else is and their maturity and why they’re. Still working and happily employed. And I’m someone that comes with a warning label because of past misdeeds is that Chris Belair, who I know you’re friendly with and Chris Belair, uh, from listening to your Carson podcast, uh, I heard the story when I believe Bill Scheft was on, and he told that famous story about there was a night when David Letterman really wanted to listen to the Eagles and so he’s like, can’t we listen, can’t we play some Eagles? And Paul saying, no, no, no. Anything we play is going to cost us a million and Rob’s yelling at him. No, you can’t do it. And, um, Barbara Gaines is saying, no, no Eagles. You can’t do it. So Chris Belair’s day is done at that point. He’s done his writing. It’s the middle of the show. Dave’s just screwing around and Chris Belair. Goes and looks up on their MIDI music file, like it’s all the, the archive music and the royalty free music. And just look, spends the whole show out of his own free will, looking up songs that maybe would sound like the Eagles until he finds one that sounds like life in the fast lane and gets it, sends it down to the studio, sends it down to Bill. They play it and they play it on the show. And it’s a classic bit from Letterman. And it’s because Chris went the extra mile. Chris is a good person. Agreed. Chris will be a team player. And he worked out of his position that day and created a classic moment because he was helping out. Now, me, that day that Trump was on the show, I’m, In a bad mood because Miles left me a whole bunch of stuff to read that he didn’t get to. So now I’m feeling like, uh, on top of all the stuff I’ve got to read, now I got to read everything that he didn’t get to from Thank yYou notes or whatever. It was some bit or something or something for the mono. Maybe it was like a joke bit for the mono, but I got to read through everyone’s jokes for this. And an email went out to me and three other writers that said, we need more Trump questions. And said, we want them from you guys because you’re the dark, darkest joke writers we have, you know, you think of make it funny, make it interesting, whatever. And I started to do it. And then I said to myself, you know, I’m already doing some of Miles’s job today. And. I’ve been here for, I think at that point, seven years. So I’m a little bit jaded and I’m tired of doing other people’s jobs. I’m tired of helping out when there’s a sketch that’s short. I don’t, I’m just not going to do it. And so when I woke up that next, I think about that every time I see that hair tussle and what it did to our show. And I look at none of us helped out. All four of us said had the same bad attitude that I’m busy with something else. I’m not going to do it. But all I had to do was submit maybe two or three questions. If one of them gets on there, maybe that interview goes different. And I always tell that story. Like when I taught at Emerson, I tell people that story. I say, I was selfish. I was immature. I said, I don’t feel like being a team player today. I’m not playing out of position. I’m not doing it. Whereas someone like Chris Belair will go that extra mile. So, you know, yeah, it’s when people say, well, the hair tussle wouldn’t have been as big a deal if Jimmy had asked some questions, I always say to them, Hey, I was asked to submit some questions that day. And, uh, I just said, I don’t feel like it. And I knew I wasn’t going to get in trouble because at the time I was, you know, untouchable or whatever. The next morning I watched the interview in horror because, uh, you know, I’d gone to bed and everything, uh, the night before it was a rare night where I’d gone to bed early, but people were waking me up and saying, What the f*ck man? What is your boss? What’s going on here? And I saw the image and I was like, I don’t get it. And then I watched the interview and it was a life lesson learned too late. That was like, man, do what’s asked of you. Be a team player. If you can, if you can contribute something in a different way, you really should. And it could, it could make the difference. In Chris’s case, it created a classic comedy moment from an iconic show. And maybe if me and one other person had written some hard hitting questions that day, maybe the hair tussle never even happens. Maybe Trump is in such a bad mood. He says, f*ck you and Jimmy looks even nicer at the end. And, but yeah, it’s bullsh*t. It’s it’s people that say Jimmy is at fault for Trump being elected. And that’s bull Trump. That hair tussle had nothing to do with any of that stuff. Tell Hillary to go visit the swing states. Tell her to go to Wisconsin every now and then. That’s, that’s a bigger deal than what Jimmy Fallon’s doing. Come on.
Can you share any Larry Sanders-esque moments backstage with guests or just behind the scenes where like this be, maybe get on Sanders?
My favorite day ever working there. Well, there’s two favorite days. It was Halloween, 2017. Uh, is when my daughter and my wife came in. It was the day that everyone got to meet Sadie for the first time. It was Halloween. So she’s dressed up and, uh, Patrick Borelli had had a daughter too. And so it was like this great moment for us was two guys from Boston. It’s like, you believe we had a kid, like, you know, like we never thought we’d have families and kids and stuff and here we are and, you know, Jimmy got to meet her and I got a picture of the two of them and all that stuff. That’s my favorite, favorite day, my second favorite days from Late Night. And that was when the beach boys were on. And I don’t mean like the Mike Love Beach Boys. I mean, the Beach Boys, Beach Boys, they were all Brian Wilson and David Marks and Bruce Johnson and Alan Jardine. My favorite backstage story is I’m just a diehard fan and I’d already spent the whole day hanging out with everyone. But Brian Brian’s on his own and, and was a hundred percent with it at the time, by the way. So he was. Leading that band, uh, but he was off on his own doing his own work and stuff. So I hung out with the other four guys, beach boys, all just five of us just hanging out, telling stories. But then I kind of started to overstay my welcome a little like I’d been there. Now it’s the show has already happened and I’m still there when they come backstage. Hey guys, I was like, okay, great. And I go up to Al Jardine and I start talking to Al Jardine and I’m talking to him and I’m talking to him and I’m talking to him and he says something like, yeah, well, crazy days or whatever. And then his wife comes and grabs and goes, Oh, Al, um, uh, Jimmy wants to talk to you and pulls Al away. Oh, I’m so sorry, Jon. This was great. But we’ll catch up next time. Pulls him away. So they go over to Jimmy. And Jimmy’s like, Oh, Al, Al Jardine. Oh my God. And they’re, they’re talking and I watched them talk. And then I see Jimmy, the light in Jimmy’s eyes start to go out a little bit. The more Al talks to him. Until finally Jimmy goes, “what is going on?” Which is the cue for Kelly, his assistant to come grab Jimmy and pull it. Jimmy, the car is waiting for you. You got to get downstairs. And Jimmy goes, Oh, Al, I’m so sorry. We’ll catch up next time. Does the same thing. Okay. So now Jimmy’s pulled away. And as he’s being pulled away. Brian Wilson walks around the corner and Jimmy goes, Oh my God. And he goes, I need to talk to him, puts his briefcase down and everything goes over. It goes, Brian, that was unbelievable. And he shakes his hand with both hands. And he’s like, Oh my God, you guys were, you guys were great. Oh my gosh. Can you come on and do their hearts are full of spring. Can you come on for Christmas and do little St. Nick? Oh my gosh, dude, it would be great. And he’s doing, and Brian’s going, Oh yeah, right. Right. And then all of a sudden Brian goes, yeah. Oh, he starts feeling faint, starts acting like he goes, Oh, where, where am I? What’s happening? And then everyone like Brian’s wife, his manager, Jeff Foskett, they all run over there, Brian. Oh my God. Are you okay? And then Jimmy goes, Oh my God, I’m so sorry, Brian. Thank you. And leaves. Brian gets around the corner, stands up straight, goes like this, and just keeps on walking. And so it was just walking, watching that food chain of, I don’t want to talk to anybody. Like, it was just that thing of like, the Beach Boy doesn’t want to talk to the writer, the host doesn’t want to talk to the Beach Boy. The leader of the Beach Boys doesn’t want to talk to anybody. And it was just that thing of like, and Rebecca and I still talk about it. Just like, you know, like whenever I’m having an important lunch, whatever, she’s like, just remember the, you know, remember the Al Jardine moment. Remember when it’s time to bail? And I’m like, yeah, yeah, yeah, yeah. But it was like seeing that happen and then feeling not as bad. Like I was like, Oh, Jimmy just got blown up, you know, like it happens. So yeah, we, there’s stuff, there’s other stuff I can’t talk about, but, uh, out of respect for people. But that was one that stuck with me as a very Larry Sanders-y moment where it was like, no, it’s a talk show, but no one really wants to talk to each other, you know,
You actually lived one of the Larry Sanders stories on the show, which was that they had Phil, the writer, who only be really good at his job, or he was, let me say, he was the best at his job when he was miserable and he was really, um, just in a down place and he was on the on Sanders he was dating somebody and was all happy and the quality went down. So they purposely, I think, offered, um, the woman that he was, she was dating something, I forget what it was, to break up with Phil and then he’s miserable. And then the quality goes back up. But that you’ve said in, in at least one interview that that was applicable to how you were as a writer.
Yeah. And you know, it’s, it’s advice I’ve given to other people, which is you can’t write from an angry place. Um, it’s really, uh, that’s what I did. And I did it for, you know, eight of the nine years, probably. I think I, after the first year there, I got really bored. I mean, there were days where there was a day I got like nine jokes on the show. And, uh, then I think I got 10 and it was just like, I, you get to that point and you’re like, what else is there? You know, well, the answer is you talk to your agent or manager and you figure out what else is there. And maybe you go do other things. That’s the answer. Someone like Rebecca Shaw. Or, uh, forgive me. I can’t think, I apologize. I can’t think of her, her writing and life partner’s name, but the two of them were both at the show after me and did a bunch of memorable bits and then, uh, moved, you know, they got off the show after about a year and now they have a new comedy coming out on FX. Yeah, that’s what you do. You know, it’s like you, you know, and Anthony said that to me and like, you know, he was always urging me to go, but instead I stayed, I needed the money and I wanted the money and I loved 30 Rock and I loved being in New York, and I loved Rebecca and I didn’t want to make her move to California and I didn’t think she would. So I thought that that would end that. And, um, so after the first year, I just got really bored. And started acting out. It goes back to when I was in school. That’s kind of how I was in school. I would go up and down. I would get really good grades and everyone would be happy with me and I’d get bored with it. So then I would act, I would say something smart aleck-y in class, right? I’d pick on something or whatever. It got to the point where the only way for me to motivate myself was to kind of get mad was to find a way to like, you know, be like, you know, I’ve, I’ve always gotten a joke on every Friday, so I have to get jokes on today or else I’m going to lose my streak of Fridays and I got to really make sure no one can bother me while I’m doing it or man, it’s Friday and I’ve only gotten 12 jokes on this week. That means I got to get at least, you know, three more, I’ve only gotten 11. I’ve got to get four more than the normal three or whatever. And. You know, when you’re working with people like Jen Statsky or Morgan Murphy or Eric Ledgin, people who’ve gone on a great, great success in this business, but are famously mellow, easygoing human beings, as opposed to robotic, sort of almost militant writers. That doesn’t rub off so well on them. And when it’s time for them to go, you’re kind of the first one that they bury that they’re like, man, I’m glad I don’t have to work with that guy anymore. So you’re right in that every day or night, depending on how I was doing it, that I was in just a really good mood, the jokes would be soft. And every day that I came in ready to fight and ready to guns blazing. And the shirt was, you know, rumpled just cause my shoulders were up and everything, I killed it. And I got really good jokes on. And I think that I mentioned that day of October of 2017 as being a favorite day. And it wasn’t just a favorite day because of the circumstances, that was one of the rare days where I just had fun. And it was, you know, I just had fun with everything and it was Halloween and, um, I just said, I told myself, I said, look, my wife and my baby are coming in. I’m not going to be an a**hole today. I’m just going to break character. And dude, our monologue was off the hook that day. We were so good. Everyone got something on. Everyone got multiple jokes. I think we did about 20 something. I got six and they were all fun and laid back, but I didn’t learn anything from that. Like I didn’t like, it was just like, as soon as the next day came, you know, I, I was never someone who would go around picking on other writers. I was not, despite the bullsh*t and the rumors and the stories that have flown around, I was not someone that yelled at writers, uh, working under me. That is not true. Uh, in the year and a half that I was there with filling in for Miles, I made it. That was my only goal was let’s get through this without yelling at anybody. So I didn’t yell at anybody. Did I have to say to somebody, you know, I won’t name them because they’re still there, and I don’t want to create drama, but like there was someone there that, you know, I had said, uh, no more Trump jokes. Jimmy said, we’re all set. We got eight. That’s it. We’re doing them. And the very next batch of jokes I got were three Trump jokes. Did I call that person up and say, Hey, what the heck is this? Yes, I did. I didn’t yell at them, but the thing is when you to write your own stuff, give off this aura of being unpleasant, being unhappy, people stay away. They don’t know what your deal is and they think they might take it personally and they might think, oh, he’s mad at me and he’s giving me some, it’s like being a porcupine. And so, yeah, it was, I wrote from a place of anger for many of those years and have since learned how not to do that. And it’s, you just have to, I didn’t even realize it, but it was just, Rebecca said at one point. There was just one point where we were all having dinner, the three of us, me and Sadie and Rebecca. And she just said, you know, I’m so happy that you’ve gotten to the place that you are. And I was like, what do you mean? And she’s like, and I go, am I that different? And she’s like, yes. And she went back and named all these times when we were together, where I was just making up things to be mad at, but you just can’t do it. You’re just going to drive yourself into the ground. And, you know, like when Statsky won her Emmy, her latest Emmy, I sent her an email to congratulate her and I didn’t hear back for a couple of days and I started to get that pit in my stomach where I was like, like, is this another per and when she wrote back a really nice email, it just felt so good that it was like, maybe, maybe the words getting around that it’s like, you can talk to Rineman, like, it’s, it’s okay. And, you know, but it’s, um, if I’m a cautionary tale, Hey man, I had it good for a long time. You know, uh, hopefully other people can learn from it and have a really good career.
This happens on other late night shows. I mean, it’s something that you, um, you, I mean, your story of just how hard it was and all the obstacles and we’ll get to everything, um, a little later, but you were known in the beginning, you, you said, quote, as a rookie with a temperament. And you said that Miles and Jeremy had to sit you down and said, you have to stop acting this way. What was your response to them? Did you see that?
The way they framed it was, and they were right, is that, uh, You know, when things ultimately broke for me, it was January 8th, 2018. So, 1/8 ‘18. And I had a TIA mini stroke.
On the subway?
On the subway. On the PATH train, yeah. And, or no, it was on the, you’re right, it was on the subway. And somehow I got on the path. I don’t remember how I got to Hoboken home, but I did. And what they warned me about, this is 2009. So this is almost eight years. This is like just over eight years beforehand. The way they framed it was not, I wish they had framed it as you have to stop doing this or else we’re going to fire you. I wish they had said that to me. That would have woken me up real good because my dad was still around at that point and, uh, the thought of having to face him after f*cking up at this great dream job, that would have, and you know, other people that were mentors in my life who were around at that time, that would have woken me up real good. And it would have, you know, You know, and I’m sure, I’m sure Miles would say, yeah, I can wish I did that too. You know, like it would have been, but it would made his life a lot easier for at least a couple of weeks. I wish they had said you had to stop doing it the way they framed it was. You’re, you’re going to burn yourself out. You’re going to hurt yourself if you keep taking it this seriously. And if you keep acting like this and the irony of it was I was angry because of the way it wasn’t my joke didn’t get on. It was an element joke, meaning there was a sound effect and I wasn’t happy with the way it was executed. It’s still got in the show. I got credit for it. Jimmy liked it. Lorne thought it was cute. The audience laughed, but because it was only 80 percent executed the way I wanted it to, I was furious. Like I was fuming, and I, I sent them both an email and said, I wish you would just cut this joke. And they sat me down and Jeremy did that many, many times. And then after Jeremy was gone. Miles said many times, like you really, like you would say, I know coming from me, this may not be what you want to hear, but maybe you look into therapy, like this could really help you. But again, it’s like you talked about the guy from Larry Sanders where it was just like all that mattered to me was how well I did at that job and how many jokes I got on that show and that they got funnier and funnier. And then I got more and more and then I, you know, fed that beast. And there was this personal. You know, cause I used to be a distance runner. I think it was that mentality of don’t stop, don’t slow down. As soon as you slow down, things are going to hurt. You’re not going to be as good. You’re going to tighten up. And, um, I just didn’t listen. You know, I would listen for a while and then something would happen again and I would act out. But you can’t, how do you punish? When you’re a show that is new and trying to stay on the air, because Dick Ebersol is, you know, from reading, uh, uh, Bill’s book.
That would be Bill Carter?
Bill Carter. Yeah, I, you know, you know, from reading his book that Dick Ebersol was poking around trying to get us kicked off the air. He was trying to have it be Jay and Conan again. And so when you’re the number one writer, even as a rookie on a show that is on the chopping block, because they’re trying to cut a late night show, they’re not going to punish you. They’re just going to give you talks. They’re going to talk to you. They’re going to tell other people like Morgan, like Allie Waller, like Eric Ledgin, they’re going to tell those people, Hey, just deal with them. He’s crazy. When you leave the show, you never have to deal with them again, but just, we have to put up with them cause he’s good. And we’re trying to keep going here. And then there was always something like that. Then it was, we were trying to get the tonight show. And so when you’re trying to get the tight show and I’m being an a**hole again, and I’m treating Jeremy like garbage, what are you going to do? You just tell everybody, just deal with it. You know, something I’ve done. In between, like when I was, like I said, I’m going back to school and I’m completing my master’s degree and something I’ve done just to have something to do on some days, like, you know, you don’t do it to get rich, but I’ve been a substitute teacher and I’ve gone back to the school I went to my elementary school actually, and I’ve been teaching sixth grade and, you know, you, you learn your attitude with certain kids who act out is, well, they’re not following the rules. They’re not doing what I told them, but they’re not bothering anybody right now. It’s like, if I go poke the bear, they’re going to bother the rest of the class. If I let them just keep break the rules and watch YouTube on their computer and they’re not bothering anybody, to take the win. You know what I mean? And I think that was what Miles’ attitude was with me, which was as long as I, as he can put out the fires with everyone else that I annoy, just let them get away with it. You know, that’s just the business side. And, you know, you always think that like you’re invincible, you know, every time you get, every time you get away with another transgression or, and again, I was, it was never anything like scandalous that you get fired over. Like it’s never anything you read about. I, I was not someone that went around picking fights and making fun of people. I was not someone that I always root for the underdog. So I was never going around making fun of people’s clothes or making fun of new staffers are in, I was always nice to the interns. I obviously didn’t sexually harass anybody. That’s I don’t even know how to, you know, that’s, I mean, you can see, I mean, this is, I’m dressed like Forrest Gump f*ck’s for sake, um, you know, but I was just unpleasant and you always think with each turn that I’m invincible and I’m never, I’m always going to get away with it. Man, there’s always someone for each of us. There’s always going to be someone that comes into that job and comes around the corner and they’re going to be carrying a big, big club that you didn’t expect. And they’re going to have your number. And when…
We’re going to get to that in a little bit, but I mean, your whole journey, I appreciate you being just so honest. I mean, the thing is I’ve worked on late night. I had friends at late night and I’ve had people that have told me that have been let go from jobs that I didn’t do anything. I have no idea why this happened. And they tell their friends that and their friends are like, I can’t believe they didn’t you I’m so sorry. And then I then I’ll talk to like other people that worked at this show and they’ll tell me actually what happened. You’re you’re taking responsibility. A lot of these people. I don’t know. I didn’t even do anything. They’ll tell me they did this this this and this.
Well, it took me a long time Mark to get to that point. It took me a long time to understand Be mature. And I know we’re both wrestling fans and someone I got to work with for a little while. And I, I mean, I’m listening to his podcast really changed my life. Guy by the name of Bruce Prichard.
Absolutely. I know who he is. I used to watch him at Hershey Park arena when he was Brother Love.
Brother Love. And now he’s a very divisive figure. You know, we never know day to day what’s going to happen with WWE right now. Uh, they just had another big couple of bombshell articles come out, a new lawsuit and all that. So I don’t know. I like, you know, for all I know, I know he’s close with Vince, anyone that’s close to Vince, you know, you got a target on you. So, but I can only speak to my experience with Bruce Prichard, which was very, very positive and very giving and very generous and humorous. And that’s just my experience, but his podcast, I love, and. Changed my life, it changed the way I look at things because he owned up to the way he behaved and I listened to it and I said, two things, man, that sounds a lot like me, you know, he’s a guy that got fired and he was gone from the business for 11 years until he finally got brought back the part two of that was, I wish I’d listened to this podcast while I was at Fallon because there was a lot of warning signs and
Can I interject real quick though, Bruce Prichard admittedly brought a gun to a taping.
Yeah. I never did that. I never did anything like that. But you know what else you don’t want to do is if there’s someone who has a very close personal relationship with the person that makes the final decision and they’re really good friends, you don’t want to piss off that friend. And, um, that’s what I did. And, you know, then when you do that, all the stuff you’ve done in the past comes back to haunt you. And so, I was stupid. You know, like, for me, it was less like doing anything. You know, I never brought a gun to work. I never, it’s funny, because Jeselnik joked about that.
Is that fair that I mention that about Bruce? I don’t want to…
I think it’s fair. I think it’s fair. Yeah, I think it’s fair. But Bruce’s big thing was he didn’t get along with Stephanie McMahon. Yeah. And he was, in his words, I think he said he was immature about it, and he was not communicative, uh, communicative, and, um, And it was inevitable, probably, that he was going to be let go anyway, but that was something that he gave her, the smoking gun, literally and figuratively, is what, All she needed. But, uh, it was a very similar story to what I went through. And, but yeah, that’s what I tell people is that yeah, you’re invincible till they hire someone that knows that has your number. And, and
I do wanna mention that I, I don’t know the circumstance of him bringing the gun. I, I don’t know if it was un, I’m guessing it was unloaded. I think that’s what he said. I believe he said it was, it wasn’t loaded. I don’t know if he was aware it was even there.
There was a hurricane. There were storms or fires or something down near Houston, Texas, where he lives, I believe. And I think in packing up, he was, he went straight on the road and packed up like all his stuff. And ended up bringing it to the show unwittingly. And I think, or, or it was trying to get rid of it or something. I don’t know exactly. It’s it’s on Something to Wrestle. It’s on his podcast, “Why was Bruce fired.” Which is probably the best episode that he and Conrad have done. Um, but he talks about it there. He owns up to it. Yeah, he did that. I never did that. But yeah, but I will say that, you know, I like, I had that reputation with certain people in the office that, you know, yeah, I was the Dwight Schrute. I was the guy that was gonna go nuts someday, you know, so it’s like never did anything like that. But, you know, I, like I said, I was the ticking time bomb. And I think what no one realized. Was it was going to go off internally that I was going to implode instead of explode. And, you know, that’s, that’s ultimately what happened
And you did go to therapy, correct?
I went to therapy after it ended, I went through a real, real tough, rough time. I mean, I, a lot of 2018, that’s like my last year, uh, in a way.
Do we want to talk about that now? We, we, we can. This is you’re going through a divorce. You had just gotten let go from Fallon and one of your parents was sick.
Well, here’s what happened. I, I, I would say I was more pushed out at Fallon than let go. There was no, there were people there, namely Mike Dicenzo and supposedly Gerard Bradford, but I can tell you Dicenzo, for sure, that we’re fighting for me to, that we’re like basically saying to Amy Ozols, who was the new head writer that you can’t fire Rineman, you just can’t. We’re not going to fire him. She had Jimmy’s ear. She was the Stephanie McMahon of the situation. That’s so funny. I say that, cause I’m friends with Stephanie McMahon. I love Stephanie McMahon. Um, but Amy was wanting to get rid of me and so it was sort of this, uh, you, you know, just keep writing for the show, but you can’t come to work anymore.
She had been let go though, right? And then brought back. Is that what happened? I could, I, I just want to make sure…
Dude, she’s, she’s been, I think she’s been, I think it’s happened two or three times. Uh, yeah, she got let go one time that I know of. In 2013 as showrunner
From Fallon.
And then yeah, they brought Josh Lieb in instead.
Then they bring her back and then she asked to have dinner with you.
Yeah, they brought her back. And I always thought I was cool with Amy. Um, I wrote a pilot with Jimmy and Amy, uh, about wrestling of all things, uh, back in 2012 and we got real close to producing that thing and a couple of things happened after the fact, where admittedly on my part, where I think I f*cked things up with Amy to begin with was, um, this will sound insane now because it’s like ancient history. It’s like, you’re like what, but we pitched the show to USA after NBC had passed on it. And USA didn’t want to do the pilot I’d written with Jimmy and Amy. But Chris McCumber, who was the president of USA at the time, wanted to do a different show with just me. And so I basically used that meeting that Amy had set up for me unwittingly, but sort of, I kind of let it happen. I kind of turned a blind eye and cut a handshake deal with Chris that let’s go do something different without Jimmy and Amy. And to no one’s surprise, by like two days later, that thing was motherf*ckin dead. I mean, that was dead in the water. Uh, cause as soon as Amy and Jimmy caught on to that, all of a sudden you get the call from Chris. Uh, you know, I think I spoke too soon, and uh, I don’t know if we can really do anything else. M’kay, you know, it goes away. And then the flip side of that is now you got your friend mad at you, you know, Amy’s mad, like, man, I got you that meeting and you didn’t even come to me to ask, you know, like, what the hell, you know, because the ethical thing would have been for me to say to her, Hey, Amy, they don’t want to do Slam, but they want to do this other thing. Would you want, you know, come do it like, you know, we’ll all work together on this thing. And I didn’t do that. I was young. I was immature. I didn’t understand the business and it pissed her off. I didn’t know that pissed her off. And then in 2016 or 2017, out of the blue, Amy is sort of in the picture again. She’s writing jokes. Like I first realized that when Jimmy was doing Denis Leary’s fundraiser in Boston and I got there and the monologue was totally rewritten. I’d written his monologue for that. He was going to go up and do stand up at Denis’s funder. And I go, what the hell? And I go, why is this all different? And I go, who wrote these new jokes? And he goes, Amy Ozols. And man, when I heard that name, her Jimmy say it too, because like when she got let go, that was a big deal. And it was like, you didn’t mention her in the office and you didn’t mention her to Jimmy. You let, if he had a story to tell that mentioned Amy fine, but you didn’t bring that name up. It was almost like bringing up an old writing partner or someone, you know, it was like a Farrell/McKay sort of situation. And all of a sudden she’s back. And when I heard she was coming back to be head writer, I loved the idea. I loved it. Like to me, it was great. Cause I, I felt like she didn’t get a fair shot in 2013. I loved that she was coming back. I felt like a great redemption story. Yeah. And then she asked to have dinner with me and during the dinner made it very clear that she thought I should leave. And just asked me, you know, why don’t, why don’t you go do something else? Why don’t you develop a pilot with Lorne? Why don’t you go do this? Why don’t you go do that? And when she’s saying this to me, this is right after I finally, after all these years had fallen in love with the job and the show and I had let that anger go and I had really, you know, I had a dog, you know, when you come home to a daughter and she comes up and crawls across the carpet and gives you a big hug and you’re trying to get things right with your wife and everything you let that the work anger go, but now it’s like right when I fall in love with it. She’s saying, why don’t you leave? Yeah, shortly there at that night, as a matter of fact, on the way home is my passed out on the subway.
It was the mini stroke.
The mini stroke and. Then all of a sudden it was like, I just couldn’t write anymore. Like I could read people’s jokes. I could edit, I could put together a motto, but I didn’t have the same brain for several months to write. And then Amy came into the office. So now I’m trying to manage up a little bit too, which I had not had to do. Like the reason it had been so much fun is that. It was just me and Jimmy, like I, I was, I mean, you know, at first it was very difficult, you know, there are stories that are out there that they only really have half the story or a third of the story, but there’s some that I hear and I go, I remember that, like I was, I was part of that or I got, I got it pretty bad that day and it was tough with him at the beginning, but then once he trusted me, it was fantastic and I could email him and say, Hey, Jimmy, I don’t have an opener. Every opener I have here is really dark. It’s either going to be about Trump or it’s going to be about Matt Lauer or it’s going to be about, you know, Charles Manson. Like I just said, like, I don’t know. And he would write back, don’t worry about it. You know, we’ll figure it out. It’s going to be great. And it was amazing. And it felt, it made me feel so good. Then all of a sudden Amy’s there and I can’t talk to Jimmy anymore. And it’s like anything that’s said to Jimmy, I got to go through Amy. I noticed that after I had that dinner with Amy. Jimmy didn’t really talk to me anymore. And if you watch to go back to the wrestling theme, the 25th anniversary or whatever it was a Monday night Raw, uh, from the Barclays center. Yes. Raw 25, the four of us are sitting there. A ringside and Jimmy and I are on different ends. Jimmy purposely made sure Gerard and Amy were sitting between us and he didn’t talk to me the entire show. So I mean, this is, we both, we wrote a wrestling pilot together. We both loved wrestling. We talked about all the time and that night when he didn’t talk to me at all, I was like, uh oh, something’s off. And it was really just a harbinger of things to come over the next couple of months. So that was sort of the beginning of the end.
There is a lot more drama that I would love for you to come back. I mean, I have three pages of notes still here from things that I want to ask you about. Um, I do want to mention that we talked about the last time your book is out. It came out in June. That is the garden is always greener. I know also you got a blurb from Jay Leno. I mentioned the last time Gary Gulman, uh, Wayne Federman. Uh, so that is out now real quick. Just talking about the, you love the Celtics and I know you, this is a. Basketball writing about basketball. What was that like working with Larry Bird when he came on Fallon?
So that came, that was thanks to Gerard Bradford. He’s the one that made that happen. Uh, we had a story around Thanksgiving that, uh, The Bird Flu was, was out and everyone had to be scared of the bird flu. Can you imagine that? A pandemic? Unbelievable. So this is 2015 and I said to Gerard, you know, it’d be really funny is if we said there’s a bird flu, uh, let’s check in on it right now. Uh, how’s it going, Larry? And we just cut to like Larry Bird, like sneezing. And then he goes, that’s actually really funny. I go, yeah, yeah, yeah. Cause I think he’s, Gerard was always ribbing me. He’s the same guy that convinced me that all the malls closed down in New Jersey on the weekends and dumb sh*t like that. And then I’d go home and yell to my wife. She’d be like, that’s not true. And then Gerard would be like, you f*cking idiot the next day. But so I thought he’s ribbing me. Like, I’m like, yeah, right. Whatever. So then I get an email from Risa Abrams, our writer’s assistant and producer. Uh, by then I think she’s producer, the coordinating producer. We had an email from her, The next day saying, Hey, Larry Bird said yes. And I’m like, yes to what? And she’s like, isn’t it your bit? And I’m like, wait, Gerard, like you guys really redid this? And she’s like, yeah, we reached out to the Pacers. And she goes, he called back 20 minutes later and said he’d do it. So we go in and it’s on Skype and Larry wants to do it at 8 a. m. His time, 9 a.m. Our time. Sharp. Larry Bird’s Larry Bird. He’s ready to, he’s ready to shoot early every day. And so we go in there and the screen comes on and there’s Larry Bird. And his, he has one line where he’s got to say, he’s go, you know, how you feeling Larry? And he goes, not too good, Jimmy, go Pacers. So he does it the first time. It’s great. Like we could get out there. And then he goes, let’s do it again. I think, I think I got something for it. Let’s do it again. So he says the line again, he sneezes and does something else and goes, okay, so, you know, go Pacers. And we got, we’re like, Larry, thank you so much. He goes one more time, let’s run it back one more time, boys. And we’re like, all right. And then he gets, he gets the Larry Bird game face. And then he goes. Not so good, Jimmy. Go Pacers. And he says it was like a twink. He makes his eye twinkle somehow and somehow it’s perfect. So it’s like, we’re all just like, Oh my God. So, you know, Chris Tartaro says, thank you, Larry. That was great. Uh, Chad Wollett says, you know, Larry, that was not every bird. Thank you so much. Thanks for coming on. Gerard says, uh, thank you, Larry. It was great. And everyone looks at me. I’m the last one. And Larry turns his head to me and I go. This is day before Thanksgiving, mind you. And I go, Merry Christmas, Mr. Bird. And he, he goes, he kind of pauses. And then just turns off the Skype. And I’m like, Oh..
We have all had that happen to us.
But dude, by the time I got Gerard must have called her or sent her an email or something. By the time I got home, Rebecca just goes, Merry Christmas, Mr. Bird. How do you know? And she goes, Oh, I’ve heard everybody. Everybody knows our neighbors knew as well. It was horrible. Like it’s, so I, uh, people say, how was it meeting Larry Bird? I go, it was great till I met him. It was great till I talked, you know, but he was, it was awesome. He was, he was a real pro. He’s really funny. So he’s cool.
I’m glad that you, you had that. Will you come back again?
I’d love to.
In a third episode. I want, we have to do this to conclude on how everything went down with you and. You built your life up and the Correspondents Dinner, and then you doing stand up on the show and you almost, um, injuring Lorne Michaels. So, I mean, we have a lot to talk about.
That would be great.
Thank you so much for being on again.
Thank you, Mark. gardensgreenerbook.com. Go get it.
