He’d already been bumped from the Letterman show three times. Then, as he was waiting backstage to finally make his debut on the show, he started hyperventilating. Just another day in the life of comedian/writer/podcaster Greg Fitzsimmons, who ending up killing it on the show that night.
He’d go on to make dozens more appearances on late night television—with Letterman, Kimmel, Conan, Chelsea Handler, and others. So many, in fact, that Mark Malkoff had to remind him he’d been booked to appear on Jay Leno’s Tonight Show the night of 9/11.
This week on our Inside Late Night podcast, Fitzsimmons shares those stories and more, including what it was like to be hired (and then fired) by Bill Maher as a staff writer on Politically Incorrect early on in his career. He also discusses writing for (and playing ping pong with) Ellen DeGeneres in the more carefree early days of her long-running daytime talk show.
Click the embed below to listen now, or find Inside Late Night on Apple Podcasts, Spotify, or wherever you listen to podcasts.
Watch Greg Fitzsimmon’s 2024 standup special You Know Me on YouTube. For tour dates and more, visit his official website and/or follow him on X and Instagram.
Show Transcript
Mark Malkoff: Greg Fitzsimmons, nice to see you.
Greg Fitzsimmons: Mark. It’s a pleasure. Uh, thanks for hanging in with me to schedule this. I know, uh, I, I had a lot of, I’ve been very busy and, uh, and I, I enjoyed, I did your podcast once before, didn’t I? A while ago.
I must have had a guest host, like Lena or somebody else like person because I wasn’t there. But, um, we do have a connection, though. That’s what I was going to mention a little bit later, but let’s do it now. So I’m the door guy at the Boston comedy club in the mid nineties. And I have to ask you a question.
No…
Yes, it was after Neal and after Sarah and I have to, that’s Neal Brennan, Sarah Silverman. I have to ask you a question. So. You would come with the book bag. You’re always with the book bag just to see you’re dating. And you’ve talked about this publicly. It’s in the New York Times. Sue Costello. You’re dating Sue, um, who was going on every night at the Boston. So you, you would come over, but you would never go on stage when I was there. Why was that? You would just come to see Sue and say hi But you’re doing all the other clubs and stuff. Do you remember?
I mean I used to go on the Boston a lot. I think maybe I got to where, um, I don’t know
I have a theory
What?
They sent me over one time to talk to Ray Romano and ask him if he would come over and do Boston. He’s just like, and Louis CK said the same thing because I had to beg him to do it and he didn’t want to, even though he helped build the Boston Comedy Club with Henry Grill and Barry Katz. Ray’s basically like, you know, my more family, more mainstream act in the Boston can be rough. I mean, I saw the Boston Comedy Club be rough and the people, a lot of the audience wanted, some of them wanted really blue material and stuff and the comics that didn’t work that way. Some of them didn’t really want to be working those rooms anymore. That’s what Louie said. And then he wasn’t famous at the time. This was like 95 or whatever.
No, I think I worked there when I first got to New York, you know, I guess, I guess it was just a lot of crowd work comics and they would beat the sh*t out of the crowd and I didn’t like the crowds.
It was tough. That was a really tough room. There would be fights. I mean, it was, it was definitely. Uh, an experience,
I think my focus is more on the Comedy Celler at that point. And then I would, I had a car, so I used, I had a Mazda 626. It was beat up. Uh, it had dents all over it. I never, why I was in New York City for 10 years. I never washed that car one single time because I didn’t want it to get stolen. I wanted it to look like a piece of sh*t, but it had a great engine. So I would go to stand up New York on the Upper West side. Then I would go to the comic strip on the Upper East side. Then I would swing by Caroline’s in Times Square. And then I would go to New York Comedy Club. And then I’d always end up at the cellar. I think Boston Comedy was a place that never really opened its arms to me. And then when I was in and I could work, I just felt like I didn’t have the history there that I had in other clubs. You know, Barry Katz was there and Jason.
Jason Steinberg. Jason Steinberg, our friend, Jason.
Jason was always good to me, but I don’t know. It just, it just didn’t feel like, I remember one time there was an audition for the MTV Half Hour Comedy Hour. There used to be a lot of auditions over there. And I remember I was just kind of coming up. I was finally got in at this, at the club. And then Jason goes, Hey, there’s an audition on a week from Wednesday for the MTV Half Hour Comedy Hour. And I mean, my heart jumped out of my chest. I was like, Oh my God, a TV credit. And so I said, yeah, that would be amazing. And he goes, all right, come by Wednesday night, blah, blah, blah. So I was, I was doing a lot of college shows at that time. And I had a run of, of 10 college shows in the Midwest. And so. This audition would have been during one of the colleges. I canceled the college, which was probably about $1200, which was a lot of money for me back then. And, uh, I booked a ticket in the middle. I, so I flew out to the Midwest. Did four shows, flew home to New York to do this showcase. And then the next day flew back out to the Midwest to finish the tour. And I get to the club and, uh, Barry Katz is there. And he goes, uh, no, no, no, you’re not on the lineup. And I was like, Barry, I just flew in from the Midwest to do this showcase. Sorry, pal. It’s that, and, and Jason’s just standing there. Like, I don’t really remember. And I was like, I don’t know. The club was kind of dead to me after that.
I get that. And I mean, he had so many of his own clients, I’m sure, that he wanted to throw on. I mean, it, it was incredible who he had at the time. I mean, every night at that place was Chappelle, um, you know, would come over, Darrell Hammond right before he got Saturday Night Live was there pretty much nightly. And then it was, um, I’d have to look at the list, but brewer right before he got Saturday Night Live. And then, um,
It was not a good club. It was, it was next to the cellar, which put it on the map, but it was a lot of drunks. Um, it was always one quarter filled. It was like disaffected NYU students with, you know, um, kind of urban people that didn’t give a f*ck about my style of comedy. I didn’t, you know, I just didn’t, I didn’t love the Boston.
The weekends were packed, depending on during the week. I will never forget, sorry to name drop so much during this, I didn’t know we’d talk about this, but I’ll never forget that summer, I think it was 95. When Chris Rock had just, he had left SNL and it was before Bring in the Pain and he was, I had no idea he was basically being Rocky and going to every single club.
Yeah.
To get stage time. Even though once, I couldn’t believe he wanted to get on stage. I’m not the door guy and he’s like, can I get stage time? And I’m like, Chris Rock, of course. And he went on and it was like what you were saying, a Tuesday might have been. Uh, 12 people in there, maybe something like that. And it was purely, and he talked about it later, just, he was going to any club he could, the, you know, the Carolines or like the lowest, the lower ones, not that the Boston was the lowest or lower, but he would just to get in front of any crowd. And then I saw his special and I’m just like, he was Rocky.
Well, dude, he, at that time, he was, he was telling me at that time, his agent dropped them. His manager dropped him. He couldn’t get arrested. Like, his career was completely stalled out. And, uh, I think everybody watched him. And the thing about Chris Rock is, like, he’s one of the best comics to ever do it. But he’s not like a Chappelle. Chappelle walks on stage and he could read the phone book. I mean, that guy is so funny. His style is so good. His confidence. Chris is not that kind of comic. He goes up with new stuff and it does not go well. And then he’s a craftsman and he puts sweat, blood, sweat, and tears into it. And he turns that material into brilliant material. And the, and the confidence comes. Even now, I see Chris do new material, and it’s just not the same as watching Chappelle do new material.
It’s incredible. I mean, I opened up, I can’t believe, I never thought I’d be talking about these stories. I had a sketch group, we opened up for Chappelle, um, this would have been, like, late 90s, maybe? Right before he got his Comedy Central show, we’re at James Madison, and they’re booing us, this is an opening act, even before we say anything, because they just want to see Dave, uh, Chappelle. Contractually, the guy has to do 90 minutes per, he’s doing two shows. And the first one, I think he did two hours and the second show, and I’m not exaggerating, was three and a half hours. I mean, he,
And how old is he at this point?
Oh, goodness. In 2000… I don’t know. I mean, probably in like late 20s, maybe maybe 30 and he’s reading out and it gets to the point where he’s just reading out of like his notebook and getting as many hard laughs as he was getting with prepared material, right? And the guy was unbelievable. And I remember afterwards, he was very, very nice. He hung out with us and he’s like, Don’t I know you? I’m like, Yeah, I used to be the door guy at the Boston. He was very, very kind. Um, to me, but the evolution, no, he would be, I remember he’d lived in like Union Square and that building, and he would just show up to the Boston without doing any prep. I remember seeing him in the fountain at Washington Square Park, the summer of 95, just doing a, like a pop up thing where nobody really knew who he was at this point. And he’s just holding court and stuff. The guy was unbelievable, but he would just kind of show up and, and wing it and kill.
Well, his hero was that guy who, who, that’s how he started was in Washington,
Charlie Barnett, it was Charlie Barnett
It was, and like, he was very tight with Charlie and he really was like, Charlie was like a role model for, for Dave.
Yeah, he wrote a screenplay, I remember, around that time Dave did that never got produced called King of the Park or something like that, where I think I think maybe he wrote it or somebody, but there was talk. Maybe he’ll go back to it and stuff. But no watching Dave. I mean, I have to. I do have to say from 95 until I saw him at James Madison. He was almost unrecognizable in terms of the story. He had the same great persona and point of view, but in terms of his material and in terms of like his just ability, I just was blown away. I mean, that, that all happened. I mean, after a couple of years and stuff, because when, when I moved to New York, everyone’s like, this is, this guy’s going to explode, but it took him a while. And I mean, if people watch his very first Letterman, I remember watching it, he did okay. I mean, I remember Jeff Ross blew the lid off the place, um, soon after right before… Ray Romano. Dave just did okay with it. And I was just like, this guy, maybe he needs a little bit more time. And it did take him a little bit more time. I mean, he was always really, really funny, but I think to maybe. To get to where he needed to be Dave Chappelle. He just needed a little bit more time. Um, which I don’t think people really talk about, but, um, when I saw him at James Madison, I was like, who is this? This is Superman. And right after that got this comedy central show and just absolutely exploded. But I do want to segue into Letterman, you are the only person to my knowledge that was hyperventilating backstage before their Letterman appearance. Yeah. Now, can you talk about that? I have hyperventilated on stage before. I mean, I haven’t hyperventilated in a long time, but when I used to go on stage, um, I did it before the show. I would do it sometimes even during. It’s a very scary thing. This is going to be, you think, it’s going to be your very first Letterman appearance. This is, uh, December 19th, 1995. Jack Lemmon is also a guest. Where are you when you start hyperventilating before the show?
Well, actually the Jack Lemmon show I got bumped from, I got, I got bumped three times, uh, before I did my first appearance. And Jack Lemmon was the one that I really didn’t begrudge at all. It was such an honor to be backstage and to watch him and he was on fire and they gave him an extra, um, the one I was on was with Faith Hill. And so I was backstage. And I’ve been running the sh*t out of the set. And Zoe Friedman was coming around the city with me. Uh, Robert Morton looked at the set. Everybody looked at the set a million times. And, uh, I had gotten it cause I was at the Montreal Comedy Festival and I kind of like had a crazy experience up there where I went from a completely unknown comic in New York, in the trenches, doing spots. And then I got red hot at the festival and I got a huge six figure development deal with FOX. I got booked on Letterman. I got a show on the USA Network. I signed with an agent. I signed with a manager. And then I, so then I come down to the city. And, uh, and I do the set and now I’m backstage and like, I’ve only been doing comedy about seven years at this point. I was backstage and I had complete imposter syndrome. I could see Letterman through the curtain and I’m waiting to go on. And Biff Henderson is standing there and he’s got his hand on my shoulder. And all of a sudden I just start to, yeah, I started to hyperventilate and I started, and I just had to stop. And I thought about my dad, my dad had just died and he was my biggest fan. And he meant a lot to me. And, uh, so I kind of talked to my dad, you know, like we, we did this, we’re going to do this. And then somebody once said to me, pretend you already killed before you go on and then, and then go on. And so I said, dad, we dad, we already killed. So I go on stage. I got one laugh and then the universe just opened up, and I felt like I was standing on stage at stand up New York on a Wednesday night. You know, the, the bass player made a noise at one point and I reacted to it. I was like, I was reacting to the crowd. I was grounded and I had this set that I’d run so many times. It just, I just killed. And, uh, and it was material I was really proud of. And then Letterman came over and he shook my hand and he said, yeah, really great job. And was very complimentary. And then I walked off stage and it all hit me and I just started crying. I was like hysterical, and Faith Hill was about to go on and she just came up and she wrapped her arms around me and I did, and she’s tall. And so I just had my head on her shoulder and then I walk out and I saw Zoe Friedman and you know, she had Eddie Brill and they were all just standing there like that was amazing and, uh. Yeah. And then I had an after party at the Friars club with my whole family that was in the audience.
You have another distinction. I may have only heard this from one or two other debuting comics. If that is, and this was, I believe your debut was January 4th, 1996. Is that after you’re set your first time that you went on? Didn’t you actually see Dave in the stairwell?
Yes.
That doesn’t happen almost ever. No, no. He does not want to see anybody after that show unless they’re a race car driver or if their last name is Miller or Dreesen or Altman.
Well, yeah, they go out of their way. They tell you. You know, don’t be in the hallway when Dave comes through and then, uh, and then they have a PA come through the stairs, clear the hallway, clear the way, everybody out of the hallway. So like we all run in the green room and then he comes out and then I go to my green room and I’m hanging out with Michael O’Brien, who’s my publicist. And, um, my, uh, my sister was there, so we’re hanging out for a while. And then I leave and I go walk down the stairs and Letterman must have had a meeting or something. So we walked. Right into each other. And I said, oh, hey Dave, thanks for having me on the show. And then he just said the same thing he said to me on stage. He was like, uh, fantastic job. Great to see ya. Thanks for coming by and just kept on walking. And I was just like, eeeeggghhhh.
That’s, I mean, just to be able to kill like that when, um, I mean, the show was always, I mean, such a big deal for comics, but back then Dave was still, you know, I mean, by that point, maybe Jay was beating him a little bit, but I mean, it was still to go on that show as a stand up. I mean, it was such a huge, huge deal.
That was huge. Yeah,
You did something like four Lettermans. And I know that, yeah, you got that Fox deal and got it something like 300k or something back then. I mean, if you do the inflation, I mean, back then that was a lot of money. Now it is, but crazy money. And then I, I thought this was really, really funny. The first time that you, you are flying first class, your life changes. Um, I’ve had this happen before. And, um, I just thought it was really funny that you’re, you’re sitting first class and the person next to you is trying to talk to you and you just don’t want to talk to them. And. Finally, they ask what you do. You say, stand up. What do you do? And you’re like, they say I’m an actor. And what do you, what do you say? You said, if they, would I know you in anything?
I go, what have you done? I go, what have you done? And then he goes, I won an Oscar. And I said, Oh my God. I, and then he just goes, Jon Voight. And then he shakes my hand. And I was like, cause first of all, Jon Voight does not look like Jon Voight anymore. You know, he is. He changed. His look changed at a certain point, and he’s one of the great actors of all time. And so we started talking, and it turns out he was flying back to New York because his father was on his deathbed. His father was a greenskeeper at a country club in Westchester, and my father had just died. And we started talking about our fathers and we talked for five and a half hours for the entire flight. And all I wanted to do on that flight was sleep because i’d been out all night And but I at the end of it we exchanged numbers He gave me his address which was weird. And uh, he said let’s keep in touch, but then I never did because I just felt like You know, it was a perfect interaction with the guy who I had so much respect for and I didn’t want to ruin it. I didn’t want the next interaction to suck or for it to be like, that was weird. And, and so I never reached out to him. And then probably seven or eight years later, I was in, um, Indiana i was on the Bob and Tom show which was the biggest syndicated talk show in the country at that point and so I’m sitting in with them and then they said hey do you mind by the way Jon Voight has a film to promote he’s gonna call in and just do like a quick ten minute call and i said no of course not and i said i actually haven’t had an experience with him once and so he calls in and they go, uh, by the way, we got somebody in studio that, uh, maybe you remember Greg Fitzsimmons and he goes, “Fitz dog!,” he remembered me and we talked for a while and he was very warm and yeah, it was very sweet.
That’s incredible to have. Yeah, because when you’re famous like that, people are coming up to you all the time and you meet so many people. That’s amazing. When you were the warm up at Politically Incorrect with Bill Maher. What year was that? And what was that experience like?
I think that was 96, maybe 94…
It was before your Fox deal, obviously.
So maybe like 94, I think it was, it happened right before Montreal. I remember that. And it was, uh, so I was, I was living down on 25th street on the west side and the show was up in the fifties on the west side. And so I used to rollerblade to work every day as the warmup. And so I would, uh, I would go to a red light and I’d wait for a delivery truck like a UPS truck to pull up. And then I would hold on to the back of it and I would get pulled. I would get pulled up 10th Avenue and the trucks usually were in sync with the lights. So I would sometimes take one truck ride all the way up into the fifties, hanging out with my rollerblades. And so, and then I’d go and I would do, you know, and bill wanted you not to do crowd work. He wanted you to do material. So I would do material and I would mix it up. And then one day I got called into his office and he said, how would you like to write for the show? I love your material. Didn’t have to put a writing packet together. Nothing. And, uh, I didn’t even have an agent at that point. So I said, yeah, amazing. And so I came in and Istarted writing with these guys. You know, uh, Hayes Jackson and, uh, and, and Chris, um, Scott Carter. Scott Carter was there. Yep. And, uh, Danny Vermont and Eric Weinberg, who’s now in jail for rape. And, uh, he was my office mate. And, uh, we used to, we used to start the morning off, you’d get to work. This is before the internet. So Danny Vermont, no Hotchkiss named guy named John Hotchkiss used to put together the Hotchkiss report, which was a list of. Uh, he put down a paragraph for all the top stories in the news. And then you had until 11 o’clock to write 40 jokes. So you’d crank out the 40 jokes and then you’d go into meetings and you’d talk about the show that day, who the guests were, what, what the topics were, um, what their opinion would probably be. And then you go off and you write jokes for Bill. You’d write jokes for the guests. And then you’d, uh, go to the taping, see which of your jokes got picked. And then, uh, and then there’d usually be a meeting after the show where you talked about the next day’s taping.
They didn’t make you do warm up when you were a writer, did they? Cause sometimes on the show is the, the writer will still go out like Mike Sweeney or whatever for a while or Brian McCann.
No, they replaced, they replaced me. I think with Danny Vermont, when I, when I stepped down.
So this is the CBS Broadcast Center. So how, how long were you a writer and what led you to leave?
I think I was there for two. When you’re a writer, you get, you get cycles of 13 weeks. And so, uh, and then they have to renew you after 13 weeks. So I made it to the, I was at the end of my second cycle and then I got fired. He basically, uh, you know, it was nice was, I mean, apparently that happened a lot. It was very rare. They, they bring in writers and if they fit, they, it was a very intellectual show and it was a tremendous amount of work and some of the guys there were Harvard guys and it was like that level of writing and I was still going out every night. And doing sets until one o’clock in the morning. And then the Montreal thing happened. So I missed some work and I was a little distracted. So I don’t think he saw it as, but what was great was he came in the room. He could have had Scott Carter. Let me go. Uh, believe me, I’ve been fired from other writing jobs and it’s usually not this ceremonious. He came in and he sat down and he said, I wanted to be here because I want to tell you, you did a really great job. I don’t think you’re a hundred percent right for the job, but. You know, uh, stay in touch and blah, blah, blah. And, uh, so it was very, I thought it was very classy the way he did it.
I love the fact that you’ve had so many experiences in late night and just what was it like being at the Friars Club when you were a kid just because your dad was famous if you were on he was first of all he was the host of Good Day New York and then he’s on the radio and back then especially you were famous. If you were a local person like that, especially in a major city. So you’re going to the Friars Club. Do you know that when you meet Milton Berle, who Milton Berle is? Can you appreciate this?
Oh, yeah. I mean, I was raised on comedy. My father loved comedy. I collected comedy albums. I used to watch The Tonight Show with him and I, you know, my first concert ever was Steve Martin when I was probably 10 years old and I had memorized all of the albums and So, um, no, I was very aware when I met Milton Berle and Henny Youngman and, uh, Alan King. And then there was the guys that were more Catskills guys that if you were in New York, you knew them, but maybe not nationally, but like Freddie Roman and Dick Capri and Mal Z Lawrence. And so those guys were, they really looked out. They loved my dad. My dad was the one Irish guy in a club full of Jews. And he really just like, he, he, he just made them laugh. They loved the, um, his energy. He was just, he was, he had more charisma than anybody I’ve ever known in my life. My father. So those guys really looked out for me. And then after he died, I joined the club. Freddie Roman was my sponsor and I joined the club. You know, it was a second family to me. All those years that I lived in New York.
When your dad, for over a decade, was doing the Jerry Lewis telethon, did he have any interaction with Jerry, or it was just they would cut to the local, the local around the country and stuff, or did he actually work with Lewis ever?
No, they would go out to Vegas once a year, they had a convention in Vegas for a week, and my mom used to go with them, and they’d see shows, they’d see Sinatra, because my father knew Sinatra, because that’s the number one guy that his radio station played. I mean, they weren’t tight, but like, He, you know, he knew of my father. And when he came to Vegas, he’d put them on the guest list. And, and so they get treated great. My mom had a fur coat and, uh, and so Jerry would meet with everybody. And, uh, you know, my father wasn’t a huge fan. I think Jerry was not known as being, um… he was a little narcissistic. Let’s just say that.
Back in New York, you’re 14 years old. You’re with your dad at a, at a comedy club. And there’s a future, um, uh, there’s a, a guy who’s going to be, went on to do Johnny Carson numerous times. Johnny loved him.
You’re talking about Kevin Meaney?
I am. And he was the waiter…
No, no, no. It was, my father belonged to a golf club in White Plains, New York. And so there was a din… you know, they, he would eat in the dining room three nights a week with my mother and with us. And there was a waiter who was very funny. He had the, he had on the red waiter jacket and the black bow tie, which he ended up wearing as a comedian for his entire career. And, uh, he was, uh, he would come over to the table. And he would do routines. He was only, you know, probably 17 or 18 years old himself. Uh, no, maybe a little older. Cause yeah, I was, I was 10 and he’s 10 years old. So he was probably 20 years old. And, uh, he would do all these routines. Like would, would anybody like dinner? We have the New York cheesecake tonight. The cheeseboat cheesecake boats are coming. And he would sing this whole song about cheesecake boats and he would dance around. And my father just loved this guy. He was so funny. He used to laugh all night. My dad, my dad and mom would stay there till like two, three o’clock in the morning. And so. When, when Kevin first wanted to do standup, my father encouraged him. My father got him on at Catch a Rising Star in New York for his very first appearance ever as a comic. And over the years, you know, my father always told me later, he goes, you remember that funny comedian from Knollwood… Kevin? I go, yeah, of course. He was hilarious. He goes, well, he’s a big comedian now. And, uh, you should look him up if he ever comes through. I was in college in Boston, I had started doing standup. So my father was like, you should look him up if he ever comes through town. So I go out to Catch a Rising Star. It’s like 1988. And, uh, I see Kevin. And I’ve never seen a hurricane come through a comedy club the way his performance was. He had, the place was absolutely packed, line of people trying to get in outside, and he goes up, and I mean, he is sweating, and he is dancing and he’s singing and he’s doing his voices and his mother’s voice. And I mean, people are, every time I saw him, not every time, because sometimes he bombed, but in his prime, people would be doubled over, they couldn’t breathe. Their state was like, not some people, everybody was like that. I’ve never, to this day, I’ve never seen anything like it. So the crowd files out. I haven’t seen the guy since I’m 12 years old. And I’m waiting around and he comes walking out and I look at him and he goes, Fitzsimmons. I go, yeah, Greg Fitzsimmons, he goes, I remember you, account number 236. So at that point he kind of like, we started to talk and then he, he would bring me out to open for him on the road. He gave me a lot of advice. I would stay at his apartment in New York and he really mentored me for a lot of years. And that kind of transitioned into like a true friendship where, um, we got so close that like he was in my wedding party, I was in his wedding party. Um, he ended up marrying my next door neighbor who was my babysitter at the time and, uh, not at the time, when I was younger. So yeah, then, and then, you know, I’ve, his daughter is my goddaughter and, uh, you know, it was really, uh, very, very special relationship.
I love hearing that. How do you go on Chelsea Handler Show, Chelsea Lately, 40 plus times and not feel pressure? Did you feel pressure? New material? I mean, I’m guessing that they had some writers that were writing for you, but just to be consistently funny for 40 times and then do Stern something like 50 plus times. How much pressure is that? And how did you generate the material?
Well, I started out. You know, I was an English major in college. I wanted to be a writer and my father gave me advice early on when I decided to be a stand up comic instead of a writer. You know, I wanted to write books. And he was like, he’s like, just keep writing. He goes, that will always keep you in this business. If you’re a writer, you will work. And so I always took that to heart and I always had new material as a stand up. And then I started getting these shows like Best Week Ever. Which I did on VH1 for five years, where every single week, they gave you a list of topics, and it was like Hotchkiss’ Hot List, they gave you just a little brief thing. Uh, and then you’d write jokes. And so every week I’d go in on a Tuesday or Wednesday and I would have pages of jokes written, and then you would just do them for the camera and they’d cut it up. And then I did the same thing on I Love the Eighties. I Love the Nineties. And then, so I kind of had pretty good skills as a short pop culture writer. And then when I came in on Chelsea Lately, I had already written on a bunch of TV shows at that point. I started writing for TV in like, uh, 2000 when my son was born, to kind of get me off the road a little more when I did Chelsea Lately, nobody ever wrote a joke for me on Chelsea Lately. I wrote every one of my own jokes, but there was a guy there that was, uh, very helpful. Ryan, uh, he books the Tonight Show now. So anyway, uh, he would look over my jokes and he’d kind of guide me on what he thought would work.Or sometimes another comedian had the same joke, so I’d take it out. Um, but then, uh, and then it was a lot of just like, you know, sh*tting on Chelsea, sh*tting on Lonnie love. You know, Jo Koy, you know, they, they really liked it better when there was interplay. And a lot of times when I was on, we would only get to a couple topics because there’d be so much just roasting each other.
It’s incredible how many appearances you were able to do. Did you ever think in a million years when you asked Howard Stern to write the foreword to your book that it ever would turn into any complication other than you say yes, you say no. Uh, but this thing just took on a life of its own. Talk about holy publicity for a book. How did you feel though and what happened?
Well, so I asked him to write the book, um, you know, and we were pretty close. He’d invited me to his house in the Hamptons and, you know, wes regularly texted each other. And I did the show like 50 some time. He gave me my own show on his channel, which I did for 10 years every week for not a lot of money. And, uh,
You were almost Artie Lange too. You were the second runner up. So, I mean, you were very, very close to that gig.
Yeah, I almost became a part of the show. So, so I asked him to write the forward and I wrote him a note. I gave him an out. I said, if you’re, if you don’t have time, no sweat, no pressure. And then he read the note on the air and then they called me. And he said, blah, blah, blah. And I go, okay, you don’t have to do it. No, I didn’t say he goes, he goes, I’ll do it. He goes, I’ll do it, but I don’t want to do it. And I said, okay. And then he started talking about me and they were like, how, how could this guy, I don’t know this guy, how could he write, asked me to write his forward. You know, it’s just, I guess I’d rather be having sex with my wife. I’d rather be playing online chess. So anyway, he calls me up and he goes, Greg, just let me off the hook. I go, Howard, I didn’t put you on the hook. I said, I wrote you a note, gave you an out. You said you’d do it if you don’t want to do it, just say you don’t want to do it. He goes, no, you got to let me off the hook. I go, no, I go, you’re a man that take yourself off the hook. And so that turned into the conversation. And it was a bit, but at the same time, it started to feel real. And then I would email him and I’d be like, Howard, uh, I know today you were kind of yelling at me and blah, blah, blah.I go. I just want to make sure, are we good? And then he’d write back. Oh, completely. Yeah, we’re totally good. You know, uh, you, you know, then the next day on the air, so Greg writes me this email, are we good? Like, what? And then it would turn into a whole other thing. And this went on for like four or five weeks, like couple days a week, getting called. I’m in LA so I’m getting called at like four 30 in the morning to talk to him. And, uh, and he ended up writing it, but he, um, he just dictated it on the air. It was not in the end, it was not a good experience. And my book came out the same week as Baba Booey’s book and Adam Corolla’s book, which are my two biggest places to promote the book. So in the end, I don’t know how much it really helped. Uh, the book did well, we went to paper, you know, we ended up getting a second edition of paperback, but you know, uh, it, it did not, I, I don’t look back on it as a good experience.
I’m so sorry. You just never know, you know, you think you’re giving the person that out. I have to ask you, you were supposed to be on The Tonight Show when September 11th happened. Now, how does this work? Do you, I mean, you know the show isn’t going to happen, but does The Tonight Show still call you to let you know that the taping is going to be cancelled? Or how, how does that work? How soon did you hear, or do you just, you don’t get the call and you’re just like, I know this isn’t going to happen, but did you get a call?
Yeah, yeah, yeah, there was… There was a call and, uh, you know, it was, it was a quick call. Um, you know, I was expecting it and, uh, you know, that was weird. And, you know, my mother was actually on a plane. She was, she was supposed to take off at 9 AM from JFK to LAX on September 11th. And so I’m sitting at home and I’m watching these planes going in the building. And all I’m thinking is like, is that my, they didn’t tell you, they had no idea which planes these were. And so I spent about three hours waiting to hear from my mom that she was okay. And she basically, uh, they, they just got everybody off the plane as soon as they could. They told them to just get out of the airport. Don’t, they said, if there’s a taxi, if there’s a bus, get on it, just get away from the airport. So my mom who lived in Westchester took a bus to Long Island with, without her luggage, you know, nobody got their luggage. Just go. She called my aunt when she got out to Long Island, who was like 45 minutes away, she came and picked her up. And, uh, and she kept saying, I remember she kept saying, well, I’ll come out tomorrow, I’ll come out tomorrow. Cause my son was like a year old and she really wanted to see him again. And she kept doing that for like a week. She stayed at her, she stayed at her sister’s house. And, uh, she kept trying to come out, but obviously no flights left for a couple of weeks after that.
Yeah. I mean, I was here in New York when it happened. I mean, talk about surreal. Um, I was going to ask, what was it like doing Letterman show when guest host, Bonnie Hunt, uh, filled in for him because not a lot of people can say they went on with a guest host and there were only, you know, there weren’t a lot, but what was that like?
Wow. I don’t even remember that to be, I mean, I vaguely remember that, but, um, I’m sure I was disappointed, obviously, you know, you want to be on there with Dave, but. I remember they had, uh, who was the guest host? Uh, Oh, Janeane Garofalo was a guest host on Letterman one time.
I was there. No, I was there. I mean, I just left the show.I would add a day job there and I was there in the audience in the balcony. Yeah. It was her and . No, it’s when she guest hosted that Galifianakis made his network television debut.
Yeah.
He killed. He absolutely killed.
Zach wanted to come on the show and Letterman wouldn’t let him on the show.
Neither would Conan. Neither. Conan wouldn’t. Nobody would book this guy. And then he kills. And then very soon after I heard the Conan booker was at, uh, can we see some videotape of the Letterman… of the Janeane?
Right, right, right. So yeah, the guest host thing can be a good thing sometimes.
When you were writing for Ellen DeGeneres, do you have any, I know that you’ve talked about, and a lot of other people, it’s been, it was um, a challenging time at the show with her, what are some good memories that you have early on with, with her? Do you have good memories or have you blocked them out?
Oh yeah, the show started great. I mean, I think it got tough. It definitely got tough later on. There was a lot of crying, there was a lot of quitting, there was a lot of firings, there was a lot of tension. And, uh, but the first six months were great because I think she was very excited to have a show again. She was in a big down cycle in her career. Nothing was going on, but she got this show and she was really a show that she wanted to do. You know, she, she, uh. really was grateful to the writers and we had a lot of fun. It was very silly. She’s, she’s a funny, silly person, you know, and we used to play ping pong. She had a table outside her office and she was pretty good. And so she and I were very competitive playing ping pong with each other. And I would do this thing where if I slammed it and it went past her, she would have to go and get the ball. And I would say, Go over and pick up the ball. Keep walking, keep walking. There you go. Bend over, pick it up. Look what I did to you. And all the writers were watching and she’d be laughing her a** off. And, uh, so yeah, we had, we had, we were very close, I feel like, for a while and then it’s sort of faded at the end.
The show was good right away, which does not happen, um, almost ever for a late night person, or like, it, this was daytime, but just to have a talk show, Rosie was good right away, Rosie O’Donnell, it’s very, very rare. Um, when you were doing the warmup, because you started as the warmup, correct, over there?
No, no, no, I came in as a writer.
You were a writer, but then didn’t you do warm up on the show?
Yeah, they basically, they were doing some test shows and, uh, you know, so they, they had an audience and they, we did the show as if it was real. This is, you know, a couple of weeks before the show aired. And so we practiced the show and then. The producer said, Mary Connelly said, Greg, jump up and just do the warm up, warm the crowd. And so I did. And we did that for like three or four test shows. And in the meantime, Ellen was looking at tape after tape after tape of different warmup people. She didn’t like any of them. And so the day before the first show. Mary says, uh, Ellen wants you to do the warmup. I said, I’m not doing warmup, doing audience warmup on a daytime talk show. I’m a writer. And she goes, uh, well, it’ll pay an extra 3,000 a week on top of your writer’s salary. I was like, yeah, I’m good. Uh, I can do that. And so it was literally like the easiest warmup job of all time because these crowds came in and they were frenzied. They were out of their minds. And so. All I had to warm them down. I had to just, I literally went out there for 10 minutes and just said, all right, Ellen’s going to come out. No yelling out, blah, blah, blah. Stay cool. I tell a couple jokes. And then, uh, and then that was pretty much it because they had a DJ that would play music between segments. So I didn’t even have to do anything there. So I would do that. And then I would sit in the front row with cue cards and a magic marker. And during the show. I would write out jokes. We already had written jokes, but then I would write out jokes on the fly, like if something came up, she was interviewing a guest, write down a quick line and I’d hold it up. And so, uh, I did that every day on the show for two years.
Mary was Mary Connelly, the producer who worked at Letterman.
Right.
At what point, what triggered you to stop going to the production meetings? Was there an incident or was it just a buildup?
Well, I always went late. I was always late for the meetings. And when I came in, since I would always be late, I decided you can either slink in and feel embarrassed and shameful. I decided to go 180 degrees different and I would walk in and there was a guy named Derek Westerfeld, who was the executive from telepictures. He was the only guy that wore a suit, suit and tie. He was a little stuffy. And so I would walk in and I would go, uh, ladies and gentlemen, Derek Westerfeld. And the whole room would join in and everybody would do this chant. And by the time the chant was done, I was seated in the corner, had my computer up and I was ready to go and we continued the meeting.
I know that this was after you, but Karen Kilgariff was the head writer and I think this is important for me to say something and to your knowledge. And if you don’t know, you don’t have to say, but I know that the press has said that, um, you know, it was during the writer’s strike and you weren’t there anymore that, um, Ellen had fired her for some reason for, um, apparently the press, what they said is because she wouldn’t come back to the show when it was on strike, but it was the opposite to my knowledge. And I heard from a very good source that it was because. um, Karen was not thrilled that Ellen was doing shows and you know, she was, I think she was WGA and that was, that was kind of like the turning point of their relationship. Do you have any knowledge? If not, we can…
I mean, not necessarily. I will say that, you know, Ellen was absolutely a writer on the show. She was WGA when we won Emmys for writing, which I won for, she won Emmys with us. She was on the stage taking a trophy as a writer on the show. And it is absolutely forbidden for a host who’s a writer to write for their own show. And then there was producers, from my understanding, a lot of the producers were writing material for the show as well, which if they’re not in the writers guilds. You know, if it’s a Writer’s Guild show, the only material written for the show should be from writers that are signed as members of the WGA. So they were one of the only shows that continued on during the strike. And it was shameful. And I was gone by then, but I was embarrassed that the show would do that.
Garry Shandling said being on TV every day is just not good for you as a person. It changes you for the, do you think just the pressure, it was the pressure that just got. To Ellen, if you had to guess, I mean, if going out there and being consistently funny like that is not, if you have any, especially she’s mentioned she had some, I don’t know, I don’t know, post traumatic stress or whatever. It’s just not a healthy thing. Do you think that that maybe contributed? It just like it was once a week like Dennis Miller and might not have been like that.
Yeah, yeah, I think it is a lot of pressure because I saw it from the beginning and you know, you’re not just hosting a show and having to be in a good mood and present. You’re also involved in the writing of the show from the beginning to the end, approving every joke. You’re also meeting with wardrobe to get your outfit. You’re meeting with hair, getting your hair done. You’re doing promos for the show with local networks for another hour. And when the show is done, you’re, um, you know, overseeing the hiring and firing. It’s a trim. It’s like being the CEO of a company and then having to be charming for an hour on top of that. It’s a lot of pressure and the people that do it well, I have a phenomenal amount of respect for, you know, people like Conan that, you know, without exception, people that work for him say great things about him. And there’s not too many of those hosts that are around. Kimmel, I think, is like that as well. Yeah, absolutely took a toll.
I want to talk about your YouTube special, You Know Me, which is approaching 500,000 views.
Let’s get it there, people! Click on it! You Know Me!
Mom, you listen. My mom, some other wonderful people and stuff. But this special, this was done in Texas. And how many specials have you done now?
I’m not a big special guy. I’ve only did, I did two different half hour specials on comedy central. And then I did, uh, an album and then I did a special in Tarrytown, New York for Comedy Central that then went on Netflix for a long time. And then, uh, and then this last one I just did, uh, self-funded on youtube. So, you know for 35 years in the business. It’s not a lot of specials I don’t know why I just I I guess I was writing a lot on tv shows So I wasn’t as focused on coming up with a new hour every year the way a lot of people are But now i’m on a roll where after doing this last one i’m really hungry to do another one
People love it. I mean, it’s a good length. And I mean, the, the, you look at the YouTube comments and stuff. I mean, yeah, let’s get, let’s get more reviews. Did you ever do, um, I mean, you’ve all these podcasts, but, um, Fitzdog, um, definitely. I mean, you were doing, you’ve done so many episodes. Was there any episode that’s, um, a public, public figure asked you afterwards, please don’t air this. Like, I know Neal Brennan, the first time told Marc Maron, I don’t want you to air this. Was there anybody that ever did that in a thousand plus episodes? David Fincher also was another one with Maron that said, that recorded that said I don’t want this aired afterwards.
There was, uh, I got into a fight with, uh, Rob Corddry’s brother on the podcast.
Nate?
Nate, yeah, and he came on and he was promoting something and, you know, I know Rob so well, and I knew the family that he came from in the sense that, you know, they’re Boston Irish, they’re Catholic and they’re wise a**es, and they bust balls. So me and Rob just have so much fun on each other. And so I almost felt like I’d never met Nate, but I sort of felt like I must, it must be the same guy, you know? And so I said some things to him and he was not hearing it. He was not having it. And we went back and forth and it got kind of nasty. And then there was sort of like a little bit of a Twitter war afterwards. Minor. It was, it wasn’t a war. It was, it was a shoving match. And that was the only, that’s the only time I’ve had a guest where I really feel like they regretted coming on. And I’ve always felt bad about that because I’ve, I have respect for Nate. I think he’s a really good guy. Respect his work. And, um, I think it was just a tonal. I think it was obviously my fault. I had the wrong tone going into it. And it just didn’t, it didn’t gel.
It’s going to happen a thousand plus episodes, Sunday papers with Mike. Um, you you’ve been doing so much. Howard, when you were with Stern, it’s, it’s incredible how much. You’ve done. I mean just episodes. Um, do you have a dream guest? Maybe Dave Letterman?
Yeah, well Mel Brooks, but you know, I don’t know if it’ll happen. Have you tried? Yeah, he actually his son lives in my neighborhood. Max. Yeah, Max lives in my neighborhood. So I wrote a note to Mel. And I dropped it into it, which is kind of obnoxious because I don’t know, Max, and I dropped it in his mailbox, and I said, if you could give this to your father for me, and I got a note written to me from Mel Brooks from his stationery from his office, and it was kind of like. A couple of paragraphs saying he appreciates me reaching out, but he would feel strange about doing something in his son’s neighborhood. Cause my studio is at my house at that time. I think graciously, uh, declined. And, uh, you know, I still have that note.
That’s Mel Brooks. At least you got a note out of it. Yeah, amazing. Everybody that you’ve got on your podcast. Thank you for doing this. Um, you know, I, is it okay in like a year to ask you to do it again? I don’t want to, I know you don’t do these, um.
Of course. Yeah, yeah, yeah. Hit me up in a year and then I’ll be busy for five months and then we’ll do it. I know that people with their own show, sometimes it’s tough. It’s just being on the other side, but how did this go for you?
I felt really good. I love that you did all the research. There’s things that you said that I wasn’t even, I completely forgot about the 9 11 appearance on The Tonight Show. I forgot about Bonnie Hunt hosting. Uh, so this was informative for me as well.
No, I really, really appreciate you doing this. So yeah, we’ll talk in a year. All right. Sounds great, man. Thanks for having me.
Thank you.
