It happens every time. Whenever I’ve done something impossibly embarrassing or awkward, the first thing I do is tell somebody about it. Then I tell someone else. If enough people know about the terrible thing I did, after all, it can’t be that terrible. This habit of almost pathological confession has cleansed my troubled conscience again and again. For Pete Holmes, though, the tendency to share everything is more than a habit: It’s a career path.
“How much of therapy is just saying it and having another human being listen to it and not judge it?” he asks during our conversation. “But apparently I still have to go on a podcast and tell the guest about it and have the audience hear it and maybe put it on my show eventually.”
The creator of HBO’s mostly autobiographical hit, Crashing, has always leaned heavily on self-disclosure. He was the kind of guilt-stricken kid who felt so bad about calling his mother’s friend “Mrs. Mucus” behind her back that he eventually admitted it to her face. He is the kind of soul-baring man who breaks up with a woman only after consulting all of his friends with the sordid facts of the case in an effort to build consensus. Quiet introspection is one component of his emotional arsenal, but so is public pondering. The real breakthrough began, however, when he started opening up more with total strangers.
“I think there’s blood in the water and we want the whole person now,” Holmes says. “I think in other times and other climates of comedy, it could have been more okay to just get a schtick or a persona but these days, we want to know their demons, their struggles, their fears, and we want it to be based on some sort of reality.”
The first few episodes of Crashing document Holmes’s barely fictionalized counterpart ditching his more “observational” material to get personal. He talks about how he caught his wife cheating, and how she divorced him afterward–both events which actually happened–and while it doesn’t quite bring down the house, this moment points the way forward. In reality, years after he’d begun documenting his own life onstage, he started revealing everything about himself to a much larger audience every week.
Now in its seventh year, Holmes’ podcast, You Made It Weird, has coaxed many memorable revelations from its many A-list comedy guests. The most entrancing admissions, however, have come from the host himself.
“Starting the podcast was an experiment,” Holmes says. “I wouldn’t say I was very private, but I was probably as private as the average person. I didn’t like talking about my divorce. I think I viewed that as something that was embarrassing or a failure. And then when I started being a guest on other people’s podcasts, I started to uncover that catharsis, what it would feel like to really just let strangers know the deepest truths about yourself. So when I started You Made It Weird, I really was playing a game of ‘People seem to like me—what if I tell them this, will they still like me?’ I’ve done that hundreds of times and we’ve yet to find the threshold.”
When new episodes of You Made It Weird premiere each Wednesday, it’s often after a dark Tuesday night of the soul, during which Holmes considers editing out his latest overshare-y anecdote. He seldom follows through with it, though. Let that sink in for a second. All those moments in life where you spontaneously get something off your chest and then worry it should’ve maybe stayed there, clinging to your chest like a medieval breastplate? Pete has the chance to edit those moments out of his public life, but regularly decides against it. If anything, he has learned instead that the discomfort that accompanies emotional honesty is actually something to run toward, and not away from.
“The podcast trained me to go further,” Holmes says. “Like, if you hit something that’s a little bit weird or a little bit difficult to talk about, you go through it, not around it. So there were a lot of stories that came out on the podcast, inspired by things that actually happened to me, and then they ended up on Crashing. I definitely think that show is an extension of the way I learned to be very honest and very truthful, and remain funny in that honesty and truth.”
Crashing itself was born from a moment of honesty in a fictional environment. Judd Apatow was appearing in a sketch on The Pete Holmes Show, the TBS talk show Holmes hosted for two seasons starting in 2013, after the initial success of his podcast. The sketch called for Holmes to pitch terrible movie ideas to the kingmaking comedy svengali. Although there was a script for the occasion, Apatow eventually just asked the host to pitch a real idea for his real dream project. Holmes had neither time to make up a lie, nor the inclination. Instead, he shared the truth: that he was raised religious, married the first girl he ever dated, she left him after six years, and then he had to figure out what it was like being a single person in comedy. Apatow answered with his own moment of honesty: “That doesn’t sound like a comedy at all–that just sounds tragic and sad.”
Never one to be deterred, Holmes approached Apatow in earnest during the aftermath of his TBS show’s cancellation. He flew to New York from L.A., just for the opportunity to spend 15 minutes pitching the director during a break from filming Trainwreck. His idea had morphed from a movie into a TV show called Crashing, whose layered title represented a.) the dissolution of a marriage, b.) Hindenburg-level onstage failure, and c.) the structural gimmick of a quasi-homeless comic staying on a different comic’s couch each week. Apatow was interested, and he advised Holmes to just start writing episodes. By the time Pete finished writing his fifth script, he’d convinced his hero to get on board, and the two pitched HBO together–successfully, as it turned out. Now, Holmes had a new problem: how to present autobiographical material to a vast audience that would surely include the people who’d inspired that material.
Hundreds of thousands of dedicated comedy nerds listen to You Made It Weird, but millions of casual HBO viewers would tune in to give Crashing a shot. So would his ex-wife and also his parents. That same decision he was used to making each week, about whether to cut the explicitly personal tidbits from his podcast, he now had to make it on a much higher level. Ultimately, it wasn’t much of a decision at all. Pete knew he had to write the people and situations as brutally honest as possible, come what may.
“It’s definitely one of those things wear I’m shining a light on my family dynamic, and I’m curious how they will like it,” Holmes says, having spoken to me before his parents had seen the show. “I hope they will like it, and that if they don’t, they’ll still support me. But yeah, that was one of those things where I’ve told them many times, like ‘Mom, we make jokes on the show about how you’re in love with me and how my marriage always felt interrupted by our relationship.’ So I’ve told them about it. But you can tell someone about an earthquake and it becomes much more real when you see it on the news.”
While Holmes’s family may or may not have seen Crashing yet, enough people have indeed seen and enjoyed the series that HBO has already renewed it for a second season. Besides, the main audience Pete is trying to reach with his radical transparency isn’t his family or his ex, but the people out there who might have similar families or similar exes. His goal is relatability, and it’s a goal I can personally relate to. The times I’ve felt best about revealing something awkward I’ve done have been when it turns out the person I’ve revealed it to has experienced something similar. With a large enough audience, it will happen with just about any excruciating private disaster.
“The real reason to share everything is solidarity,” Holmes says. “The underlying goal of comedy is feeling not-alone. And I get the benefit of that when I’m onstage talking about what I’m going through, and the audience celebrates it and laughs. That helps me, but it also makes them feel, ideally, ‘Oh, I thought I was the only one who felt like that!’ And sometimes that can be the best feeling in the world.”