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Judd Apatow, Pete Holmes and Madeline Wise talk Crashing’s balance between reality and fiction

Crashing’s producer and stars talk what makes behind-the-scenes comedy shows work and the dangers of over-sharing.

While winter isn’t coming to HBO until April, Crashing returns this Sunday. The third season of the semi-autobiographical comedy starring Pete Holmes finds Holmes’ fledgling counterpart returning from a successful college comedy tour and, soon after, entering a new relationship. I spoke with Holmes, Producer Judd Apatow, and newcomer Madeline Wise, who plays this season’s love interest, Kat, about season 3 at HBO’s New York City offices.

“People are talking about sexual harassment and diversity and political correctness, and we wanted to address it on the show,” Apatow says. “We thought one way to do it would be to have Pete go on the road with Dov Davidoff’s character, Jason Webber, and with Ali, played by Jamie Lee. And 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.”

Madeline Wise. Photo courtesy of HBO

In episode 2, Pete meets Kat, and the two jump into an instant relationship. “I think her interest in Pete is she’s been burned in past relationships,” Wise says of her role. “I think she’s been engaged at least twice,” Holmes adds. “Both times to people that she knew for, like, 36 hours,” Wise responds.

“He’s safe. He’s not a scary proposition,” she says. “I think Kat sees in him that he’s not going to destroy her life. Or will he?”

Kat also serves to provide Pete with a level of confidence previously unseen on the show. According to Holmes, “To succeed in show business, you either need to meet a Kat or you have to have, like, an internal Kat that you make up inside of you that tells you, like, you do look good in that jacket, you do belong on that stage, this is your home, they are scared of you, you are better than them. You should keep this to yourself if it’s inside of you but, in my experience, having friends and girlfriends that do believe in you more than you do is really, really important.”

Now, for the past two seasons, we’ve watched fictional Pete gradually move away from his strict Christian faith. This season, we continue to see Pete struggle with his spirituality and question his Christian identity. “As is the case with Leif as well, when Kat talks about her spirituality, she’s really representing mine now,” Holmes says. “So, when Pete meets Kat, obviously she’s shaking his tree a little bit. She’s very honest. Pete, at this point, may not believe what he’s always said he believes, but he’s never met somebody like Kat that shows him just how safe it is to be your true self.”

Judd Apatow, who hasn’t directed an episode since season 1, co-wrote and directed episode 6, which is primarily shot in and around New York City’s famous Comedy Cellar, a location featured prominently this season.

Dan Naturman, Rachel Feinstein, Estee Adoram, Artie Lange. photo: Craig Blankenhorn/HBO

As with past seasons, Crashing features a revolving door of guest comedians playing versions of themselves. Series semi-regular Artie Lange returns. With him, Amy Schumer, Dave Attell, John Mulaney, and Ray Romano all turn up, And they don’t always play the most likable versions of themselves.

Apatow names a number of comedians he’d love to appear on Crashing including Maria Bamford, Jon Stewart, and Paula Poundstone. “We always dream that we can get Dave Chappelle to do something on the show. Chris Rock was passing by one day while we were shooting, and he seemed open to coming. So maybe next year we’ll try to write something for him and hopefully, if it’s good enough, he’ll do it.”

He also describes the show’s balance between reality and fiction. “For me, I’m generally working from a place of talking to people about their real lives and their real feelings and trying to craft fictional stories out of the material that comes out of those conversations. So even though the show isn’t true, there are moments that come from real events. There is an emotional truth to it, hopefully. And that’s what I like to write about, maybe because I have no imagination.”

Jaboukie Young-White, Pete Holmes, Zach Cherry. photo: Craig Blankenhorn/HBO

Pete Holmes is an open book with regards to sharing the intimate details of his real life with the audience. Holmes and Apatow both agree that Apatow’s job sometimes is keeping his creative partner from oversharing information the audience doesn’t want to hear. According to Apatow, “I think I asked Pete to hold back on sharing sometimes because some of the details are just so troubling, I just don’t want to hear it. Sometimes I just had breakfast and I need a break.”

“I pitched so many times Pete losing his erection while masturbating because that’s what happened when my wife left me,” Holmes says. “I felt a little bit weird, I suppose, but I would pitch that over and over. And [Judd would] be like, ‘NO ONE WANTS TO HEAR THAT! EVERYONE HATES THAT! STOP SAYING THAT!’ If anyone’s keeping the show from revealing too much, it’s not me. ”

With all the recent films and shows looking at the behind the scenes of the comedy world — from The Marvelous Mrs. Maisel, to Mike Birbiglia’s Don’t Look Twice and the Apatow produced The Big Sick, to this year’s About NinaI asked Apatow about the appeal of these stories.

“I think what’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 how can I get people at work to notice that I’m strong and then give me the next opportunity? You know, there are gatekeepers at everybody’s job who allow them to rise. And so, even though it’s specific and about standup, it is mainly about dreams and how could you make your dreams come true? What are the obstacles along the way? And I think the world of standup is filled with a lot of emotional, neurotic people, and so they’re generally more fun to watch than people who hold all their feelings in.”

And because I received such a great answer on this question when I asked Crashing writer, producer and actor Jamie Lee (Ali) last year, I asked Judd Apatow who his past comedy heroes were. “Well, I started getting obsessed with comedy during the era of The Mike Douglas Show and The Dina 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 standup comedian. And then I saw Jerry Seinfeld. My grandmother was friends with Totie Fields who was one of the first, very successful female comedians, I guess one of the Mrs. Maisels of her time. And I think she was one of the reasons why I was interested in getting involved in comedy, because she was this odd duck of a woman who was so charismatic and so funny and 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.”

Crashing season 3 premieres January 20 on HBO.

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