Crashing Season 3: Judd Apatow on Approaching Difficult Topics in Comedy

In his critically acclaimed 2018 Netflix special, “The Return,” Judd Apatow fondly recalled his stand-up comedy roots. He worked as a teenager in East Side Comedy Club in Long Island where he saw the likes of Jerry Seinfeld, Rosie O’Donnell, Jim Carrey and Eddie Murphy perform. The Huntington, Long Island club, which shuttered in 1995, became a home away from home for Apatow during a time when his parents were going through marital trouble. He joked in the special that he returned to stand-up comedy to “lower his salary and self-esteem,” but a throughline of Apatow’s career has been a fascination with the plight of the stand-up comic, from his film Funny People, to his work with Pete Holmes on Crashing, and the recent HBO documentary on the late Gary Shandling which he executive produced.

“I’m always completely obsessed with why people do stand-up, and also the types of people who are attracted to it,” Apatow told Den of Geek during a press day for Crashing season 3, which is now airing Sundays on HBO.

As an executive producer, director, and writer on Crashing, Apatow has injected the DNA of his own club experience into Pete Holmes’ semi-autobiographical story of a comedian rising in the scene. As much as the show is about Pete’s journey, the show is a snapshot of today’s comedy world where a who’s who of today’s brightest comedians drop by The Comedy Cellar, often to hassle Pete; Amy Schumer, John Mulaney, Emo Philips, Dave Attell, and many more make cameos this season.

Apatow’s obsession with comedy started at East Side, and that moment in comedy history can’t easily be re-created even with the impressive cache of cameos a name like Apatow can help attract. For the show to be representative of today’s comedy clubs, Apatow and Holmes lean heavily on their writers’ room to pull together stories from a variety of club experiences. What they came up with was a third season of Crashing that is uniquely about this moment in comedy, more so than seasons’ past, one that analyzes why Pete aspires to be famous, but more astutely the show has become a platform to work through uncomfortable topics like double standards between male and female comics, sexual misconduct, PC culture, and the rise of diverse voices in the comedy world.

In our interview with Apatow, we spoke about returning to stand-up comedy, breaking stories for Crashing season 3, and approaching heavier subject matter.

In past interviews, you’ve talked about how your experience with Amy Schumer on Trainwreck reignited your interest in doing stand-up comedy again. How has Crashing helped in that process?

Well, it was just fun to have a reason to be around comedy and around the clubs. When I was working on Trainwreck, I was beginning to speak with Pete about this show, and then I started doing stand-up again, just out of jealousy of how much fun people like Pete and Amy were having. I thought, ‘Why aren’t I having fun? I’m just sitting home alone half the time.’ It’s been really great. I’ve enjoyed just being a part of the tribe. We shoot at the Comedy Cellar, so there’s nothing more fun than that. There’s a lot of comedians around. You get a chance to show a lot of people that we love and give them parts on the show. You give them opportunities to show a side of themselves they haven’t gotten to show before.

Every season of Crashing you guys get to comment on what’s really going on in the comedy world, and it seems like season three takes that up another level. Is that one of your favorite parts about doing this show?

Yeah. We sit around with our writing staff, which is mainly comedians, and we talk about what their journeys have been like and also what’s happening right now in comedy, what are people debating, what are the politics of what’s happening in the clubs. This season, we do talk about sexual harassment and what it’s like for women in comedy, and give people a taste of what the world is really like for people.

Related: Pete Holmes on Rising In The Comedy Ranks

There’s a dialogue going on throughout the season where you guys are pushing back against white male comedians who feel victimized by PC culture and new, diverse voices taking their place. What was the discussion like in the writers room on how you wanted to tackle this topic? You guys do it with such nuance throughout the season. 

Well we’re trying to show what’s happening in the clubs, which is, in a great way, there’s a push in this industry, as there are in a lot of industries, for diversity. Then you get the natural result of that which is a lot of amazing people getting opportunities who deserved them a long time ago, but you also get a lot of white men just thinking, ‘wait a second. Am I losing opportunities because this is happening?’ I think that’s a microcosm of how people feel in the country sometimes. People are threatened by change, but it’s change that’s absolutely essential to make the country fair. The comedy world is a funny place to show how it affects people. 

Is it an evolve or die sort of thing?

Well, I think for a long time comedy was this white male-dominated industry. When I first started doing comedy in the mid ’80s, there were very few women doing comedy, and that’s changed a lot in the last 10 years. I think comedy is way better for it. Some of the greatest comedians in the world right now are women. What would comedy be without Maria Bamford? To me, she’s the best person doing comedy right now, and I think it’s only good.

For both Pete and Ali, a lot of the show is definitely them picking themselves up after missteps, or failures, or trying times. Has there been a moment in your career where it’s been harder to pick yourself up, maybe, than other times?

It’s always hard when you work on something for a long time, and then people don’t go to it. That always feels weird. What I know now, just because I’m older, is sometimes the things that nobody watches when they first are brought to the world are the things that people talk about 10 or 20 years later. We made a silly kids’ movie with Ben Stiller, that I wrote with Steve Brill called Heavyweights. It came out in the mid ’90s, and it’s just something that people continue to talk about and see. At the time, nobody saw it. It didn’t do well at all in the box office, but they kept putting it out on DVD and Blu-ray, and it’s always on TV. A lot of people are like, “Oh, my God, I loved that movie as a kid.” That happens over and over again. Now, when something bombs, I just think, ‘I’m sure this is great. They just haven’t discovered it yet.’ Maybe it is terrible, but now I can at least rationalize it.

How has your relationship with Pete evolved over these three seasons? You’re writing a little bit more in this season than the past two.

I always try to write as much as I can, just based on what else is happening that I’m working on, and Pete and I have had a really positive, fun relationship. He’s a great writer. I’ve encouraged him to try to co-write as many of the episodes as he can, and he’s a real guiding light as to what the show should be about. A lot of the writing is just sitting with Pete and a group of writers, talking about each stage of Pete’s life and career, and what happening, and then all the writers pitch in their stories, and it becomes a big soup of all that.

But he’s really fun to work with. He’s a great writer. These shows are very hard to do if the star, who’s also a writer, isn’t fast, really confident, and pushing the whole machine forward. If you have someone that needs three months to write every script, the whole machine falls apart. Pete’s definitely someone that’ll have a great idea, and go write it in a week, and then be very open to suggestions and rewrites. He’s very like Lena Dunham was in that way, and it makes it all possible.

Related: Crashing Interview – Behind The Scenes with Judd Apatow and Pete Holmes

Who are some of your favorite guest spots in this season?

We were really excited because one day we were shooting and Amy Schumer came to visit, and then we said, ‘Hey, do you wanna be in this scene?’ She’s like, ‘Sure.’ We went upstairs to this apartment, and we re-wrote this scene that she was gonna be in, but then she helped us re-write these two scenes that she wasn’t in, just because she was bored. It was so helpful, and she was so funny. That was a great day. 

It was fun to work on an episode with John Mulaney. We haven’t seen a lot of John as an actor in shows like this, and he really is a fantastic actor and so funny, so we tailored the whole finale around John, and he couldn’t have been funnier, so that’s exciting for me. I always like when you can show how great someone is at doing something where people haven’t seen them do it a lot already.

Emo Philips is someone that has been one of the greats for decades. When I first started doing stand-up, he was already one of the greats of all time. We were looking for someone who everyone in the club would get really excited when he came in, and so Emo came in. He’s a one-liner comedian, and we shot his act, and then had to pick which jokes to put on the show. We were just stunned at how amazing the joke-writing was. We had to really watch it carefully, to go, ‘Okay, we have room for about six jokes. Which ones?’ He gave us 25 amazing jokes.

Who was the last comedian to crash on your couch?

Well when I lived with Adam Sandler, when I was in my early 20s, one day his friend from college, Jack, who later went on to produce most of Adam’s movies, just knocked on the door and said, ‘I’m Jack. Adam said I can sleep on your couch this summer,’ and then he slept on the couch all summer. He became a good friend after, but that day, I’m like, ‘Wait, we didn’t have the your-buddy’s-gonna-sleep-on-the-couch-all-summer conversation.’

Chris Longo is the deputy editor and print editor of Den of Geek. You can find him on Twitter @east_coastbias.