Judd Apatow and Pete Holmes on the set of Crashing

Judd Apatow spoke to Screen Rant about the return of Crashing and his legendary career in comedy. HBO's Crashing is returning for its third season on January 20. Based on the life and career of creator Pete Holmes, the show is shot on location at hot spots like The Comedy Cellar in New York City and is as authentic to the stand-up scene as it is accessible and entertaining to more casual comedy fans.

Executive Producer Judd Apatow is a downright legendary comedy director best known for hit Hollywood movies like Knocked Up and The 40-Year-Old Virgin, though Crashing is hardly his first television venture; Apatow's tenure at Freaks & Geeks made him a cult icon long before he achieved mainstream blockbuster success.

Related: Judd Apatow Does Not Want a Freaks and Geeks Revival

During a press day for the series, we spoke with Apatow about his career in comedy, from his earliest inspirations to his time at The Larry Sanders Show, one of the most groundbreaking comedies of the 1990s, and how his experiences on that iconic Garry Shandling series compares to his work on Crashing, all these years later.

Madeline Wise and Pete Homes and Judd Apatow on the set of Crashing

Who were your comedy heroes growing up?

I started getting obsessed with comedy during the era of The Mike Douglas Show, The Dinah Shore Show. The first people I saw were people like Jay Leno and Jeff Altman. I used to watch Michael Keaton when he was a stand-up comedian. Those were the first people I saw. Then I saw Jerry Seinfeld... My grandmother was friends with Totie Fields, who was one of the first very successful female comedians. One of the Mrs. Maisel's of her time. We used to go see her when I was, like, ten years old, at the Westbury Music Fair. I think she was one of the reasons why I was interested in getting involved with comedy. She was this odd duck of a woman who was so charismatic and so funny, people loved her so much. I think, on some level, I thought, "Wow, people can really like you that much, even if you're different?" She was an inspiration to me.

You're talking about people who influenced you. I guess it's not that recent now, but you returned to stand-up yourself. Did you ever have instances where you wanted to go and perform or test out material, but you found yourself confronted with the other side of this business, of people trying to get your attention for their own gain?

I never think about it that much, if I'm at a club and I'm just trying to be a comedian, there are people there who are seeking opportunities outside of this club. But I would assume that there are people who would hope I would appreciate what they're doing. And I do. There are so many people that I like, and when there's opportunities on Crashing or elsewhere, I definitely use people that I met just hanging out. I just set up a stand-up special that I'm going to produce for Gary Gulman, one of the great comedians who works out of the Comedy Cellar a lot. It definitely does happen. There are people that we put on Crashing because we just happened to see them a lot at the Cellar and realize how great they are. But nobody is weird with me, for the most part.

Would you say you're actively searching when you go up?

I'm not thinking about it, but I'm sure, on some level, that I'm noticing and making mental notes, like, "That woman is so funny, I'll have to remember her."

Tell us about working with Pete and turning his life into a show. He talked to us about you talking him out of putting certain things on the show. You're more of a filter to figure out what needs to be disposed of, as opposed to searching for things to include.

I think I asked Pete to hold back on sharing, sometimes, because some of the details are so troubling, I just don't want to hear it. Sometimes I just had breakfast! Or I need a break. I know so much about Pete, sometimes I just need to lay off the gas. Pete has probably done more things that I don't want to hear about. (Laughs) You know, I think... For me, I generally work from a place of talking to people about their real lives and their real feelings, trying to craft fictional stories out of the material that comes out of those conversations. Even though the show isn't directly true, there are moments that come from real events, and there is an emotional truth to it, and that's what I like to write about... Mainly because I have no imagination!

There's been a rise in the number of stories about behind the scenes of the stand-up world, or comedy in general. Do you think that sub-genre is having a moment? What's the appeal of this particular world?

I think the thing that's fun about it is, it's like any other office. You're trying to figure out how to get good at your job, and then "how can I get people at work to notice that I'm strong and give me the next opportunity?" There are gatekeepers at everybody's job who allow you to rise. Even though this is specifically about stand-up, it's mainly about dreams and "how can you make your dreams come true?" What are the obstacles along the way? I think stand-up, in particular, is filled with a lot of emotional, neurotic people, and so they're generally more fun to watch than people who hold their feelings in.

Wayne Federman and Colin Quinn and Judd Apatow on the set of Crashing

You have so many guests on the show. Some who wind up having arcs, and some who just make one-off appearances. There are many more this season, including Colin Quinn and Wayne Federman. Are there any guests you want so badly on the show who haven't been on it yet?

There are a lot of people that we love, who we hope appear on the show. I think we always talk about Maria Bamford and Jon Stewart, Chris Rock was passing by one day while we were shooting, so we're open to doing something with him, I worked with Ellen at The Larry Sanders Show, and it's always astounded me how hilarious of an actress she was, so it would be a dream to have her on the show. There's a lot of people we'd like to find a way to work with. That's one of the most fun parts of the show, finding a way to collaborate with your heroes. We were just talking about Paula Poundstone the other day... I mean, there are probably fifty people off the top of our heads who we would love to cross into the show at some point. We were lucky this year to have Amy Schumer on an episode, Ray Romano, John Mulaney... It's similar to when I was at The Larry Sanders Show. In the early years, it was hard to book guests, but by the end of it, Warren Beatty was on, and Carol Burnett. It became much easier, and that's happening on this show. The community is deciding they like the show, so it's easier to get people on now. We always dream that we could get Dave Chappelle on the show. Chris Rock was passing by

Speaking of special guests, is there any sort of collaboration or pushback regarding guests playing heightened, exaggerated versions of themselves? Or do they love playing around with that?

Usually, we talk to people about the take, early on. They don't just show up on the set and go, "How come you wrote me like such a jerk?" Like, when I did Trainwreck with LeBron James, very early on, we said, "we think it's funny that, for no reason, you're cheap." LeBron James isn't cheap in real life; he couldn't be less cheap! But I think it's funny if you have money and don't want to spend it. So we'll call people and get into those ideas before we write them, see if it makes them laugh. Generally, people get a kick out of having something to play. Most people are a little nicer, which makes them less interesting.

Judd Apatow on The Tonight Show

This season, you talk about how the world of stand-up is changing in terms of content. One episode deals with misogyny in comedy. What goes into the decisions on what subject matter to tackle?

There's so much happening in comedy now. People are talking about sexual harassment, diversity, political correctness, and we wanted to address it on the show. We thought one way to do it would be to have Pete go on the road with Dov Davidoff's character, Jason, with Jamie Lee's character. That way, we could show a guy who's unable to adjust to the times. And also, to show how badly women are often treated on the road, both comedians and employees at the clubs. The waitresses have to deal with these guys who come in and think they're on top of the world and hit on everybody at will. You know, the club scene has changed a lot from when I started in the mid-80s, it's much better, but there are still some dinosaurs not getting the message. So we definitely wanted to find a way to talk about that without specifically mentioning what's going on; to show it within our world.

You directed one episode this season. Does that decision come from scheduling, or does it come from you going, "I need to direct this one!"

Sometimes it is about scheduling. If I'm able to do some directing on the show, I always want to do it. I directed two in the first season, and then I didn't do any in the second season, I don't think... It worked out that I was able to do this one, which I was very excited about, because it all takes place in the club. It's all about Pete taking his girlfriend to a party where his ex-girlfriend is having everyone watch her performance on Seth Meyers at the Comedy Cellar. It feels like a little movie, so I was excited to get to play in that space. I'm really proud of it. I think it came out well.

Jumping back to contemporary issues, with sexual harassment and the road trip episode, the comedy world at large is having a lot of fun with the Trump administration, for obvious reasons, but it doesn't really happen on Crashing. Is that done to keep the show more timeless and accessible?

It's tricky to do direct political comedy, because we write the show in March and April, and then it doesn't air until the following January or February. We always sit around going, "write a joke about Trump, but hopefully he won't be President by the time this airs!" We try to do more by talking about what's happening culturally, and the belief systems of different comedians, and getting a sense of the country, and not by talking about what happened this week with Trump. Not that I wouldn't like to do an episode about Donald Trump taking the notes from his interpreter, but we can't.

Garry Shandling the Larry Sanders Show
Garry Shandling on The Larry Sanders Show.

You talked about The Larry Sanders Show. That was a while ago, but, not that they're directly comparable, but they both have a behind-the-scenes take on show business. Can you talk a little bit about how they're similar or different?

The actual making of the show isn't that different. Both shows are HBO shows. HBO has been incredibly supportive, creatively, and they always want people to take chances and go deeper. That's why it's always the dream, to have something get on the air at HBO. For me, the shows are very similar. No one else on the show worked on The Larry Sanders Show, so they don't know how similar the experience is. There's a real comedy world we're trying to tap into, everyone's playing themselves, it's all about pulling back the curtain on a workplace. And we are working with a lead who is satirizing their own journey and their own personality. The difference is that, I think, back in the day, we did so many episodes, it was exhausting for Garry. We did 18 episodes for a few years, then I think we did 15, then we went down to 12. Garry was one of the big proponents of shorter seasons, just for his own level of exhaustion. I feel like I learned a lot from working with Garry about what would make it hard on Pete, and how to pace out the writing and how to set up the production. How do we get the most out of Pete without burning him out and ruining his life.

More: Crashing Season 3 Trailer