Greg Fitzsimmons on His New Special, Getting Fired by Bill Maher and Conquering Comedy Hell With Joe Rogan

Greg Fitzsimmons’ You Know Me, an exceptionally tight comedy special dropping tonight on YouTube, is one of those shows only made possible by decades of flexing comedy muscles in clubs. “I’ve been doing it for a long time,” Fitzsimmons conceded when I talked to the comic this week. “I go on the road 30 weekends a year, and when I’m not on the road, I’m in L.A. pounding out sets locally. And it’s been like that from the beginning.” 

Fitzsimmons, who came up in the Boston scene alongside comedians like David Cross, Marc Maron and Bill Burr, talked to me about keeping it fresh as a stand-up, getting started in the business alongside Joe Rogan and rubbing shoulders with other notorious comedians along the way. 

“I still walk on stage with a crumpled-up piece of paper with bullet points on it. I have notes where I’m trying new stuff, and I still get just as excited about it.”

“Sometimes I’ll be out to dinner with some friends. It’s 10 p.m., and we’ve been sitting there for hours, eating, talking and laughing. And then I’ll be like, ‘All right, I gotta head into town.’ And they’re like, ‘What are you talking about?’ I’m like, ‘Oh, I got a show.’ They say, ‘How much are you making?’ And I say, ‘$30.’”

“It’s just something in my balls that says, ‘You gotta go.’ It’s a home. Like a bird going south in the winter.”

“Bill Maher, that was my first writing job. I was hired to do audience warm-up. I’d only been doing comedy maybe seven years and he liked my warm-up, so he offered me a writing job. I was with a bunch of guys who are still his writers 25 years later. It’s like a club over there.”

“I didn’t stay in that club, I got fired. But you know, that just happens when you write for TV shows. You get fired a lot. Usually a producer will call you in and gently let you go.” 

“But Bill sat down with me and did it himself like a man. And I’ll always respect that.”

“A lot of comedians used to cycle through The Howard Stern Show. They called it Jackie’s Chair because when Jackie Martling left the show, it opened up a spot for people to sit in, usually during the news. It was a very jokey segment. Me and Howard just had this great chemistry.”

“(Sam) Kinison would come in and he would have stayed out all night and he’d still be drunk and he’d have a couple of hookers with him. He would take over the show, and it was magic, it was amazing. But that wasn’t what I was doing at all. I was just there to be a team player.”

“They wanted to replace Jackie’s chair permanently, and so they brought in Doug Stanhope. I was one of the guys they brought in a lot — Artie Lange, Jeff Ross. An article in the New York Post had it come down between me and Artie Lange. Obviously Artie got it, which was well deserved. He just had a lot more to offer in terms of what he had done last weekend than the guy who was married with two kids. Also, he’s one of the great storytellers of all time.”

“When I didn’t get it, Howard told me the door was open — anytime you ever want to come on the show, just let me know. And he was true to that. Every time I ever asked to come on the show over a 13-year period, I just came in and it was great.”

“I see David Arquette or Natalie Maines — there are all these people who are Howard Stern fanatics. They're celebrities, and all of a sudden, you’re in with them. It was like being part of the inner sanctum. The people associated with that show from Ronnie the Limo Driver to Gary Dell’Abate to John Hines, they’re all just amazing people. 

“It’s a totally dysfunctional family, and when you get inside of it, you feel like, ‘Wow, what the fuck is wrong with me?’”

“Working with Ellen DeGeneres — what doesn’t kill you makes you stronger, right? And I think that killed me. It was amazing watching the evolution of the show. I was brought in to help come up with ideas for the show before it launched. There was a really exciting feeling about it. It was all positivity and possibility.”

“Then we started winning Emmys, and it became very unpleasant. There was a lot of fear going around. It didn’t feel fun at the end.”

“I would go on the road, and all these Midwestern housewives would come up to me after the show and be like, ‘Oh my God, you were with Ellen! What’s she like?’” 

“I would tell them what she was like, and you could see their shoulders slump and tears well up in their eyes. They’d be like, “Noooooo! And I’d be like, ‘Yeeeeeeah!’”

“America loves to tear down its lovable icons, and in some cases, I feel like it's unwarranted. But in this case, it is amazing to me to see her going out. She's doing this new special where she’s talking about how she got thrown under the bus. Let’s just say it was warranted.”

“Joe (Rogan) and I started comedy the same week. We went to Stitches Comedy Club in Boston the same week and signed up to do five minutes. Then he was dating my roommate so we basically lived in the same apartment when we first started.”

“The show was the Monday night open mic show, and it was called Comedy Hell. The MC, a guy named George MacDonald, would get up at the beginning of the show and his first words were, “Welcome to Comedy Hell, where the pipe dreams of a bunch of comedy bozos can soar as high as the lights on Broadway or crash and burn in a fiery pit known only as Comedy Hell.” 

“One night we went out, and Bill Hicks was in town. We’d only been doing comedy a year, but he was probably the biggest influence on both of us. He was just a guy who was not gonna budge for the crowd. Boston crowds were tough. If they didn’t like you, they just shut down. And when they started shutting down on him, he went, ‘Oh really? All right, how about this?’ And he would just drag out abortion jokes, and they started leaving.” 

“After the show, he came back and laughed about it with us. That was a big moment.”

“For 13 years I have put out a podcast, and I don’t know why I keep doing it. I’m Sisyphus, the guy rolling the rock up the hill. One of the main reasons is I get to sit down with good friends for an hour with no phones on and no interruptions and have a good talk with Dave Koechner one week and Marc Maron one week and Joe Rogan one week. We just catch up, and then I put it out there.”

“It’s so weird, but I still think about how bad I wanted it in those first six or seven years when it seemed out of my grasp. When it seemed like I didn’t deserve it and I was unworthy. I’m still driven by that.”

“I still feel so much gratitude that I was let into the club. I try to hold on to that same excitement. I did a show in Louisville on Friday night, and I got off stage and I was in the green room and I actually jumped up and down because I did a bunch of new stuff that worked. I swear to God, it was like the first night I did comedy.” 

“Here’s the thing: It still really hurts when you bomb no matter how long you’ve been doing it. It hurts as bad as the first time you bombed.”

“Every night that doesn’t happen is a celebration.”