Pete Holmes and Judd Apatow Talk Crashing, Comedy in Trump’s America, and Sex Jokes

Photo-Illustration: Maya Robinson/Vulture

This story originally ran in December 2016. We are running it again now as Crashing premieres on HBO this Sunday, February 19.

When I arrived on the set of HBO’s Crashing last July, I sat down in front of a monitor to watch Pete Holmes — the show’s star and co-creator, along with Judd Apatow — meekly walk up to a table of riffing comedians. Eventually, his character is invited to join by Artie Lange, only to end up brooding in his own sense of inadequacy before he agrees to go smoke a cigarette with Dave Attell. Fans of WTF With Marc Maron have heard about the famous “comedians’ table” upstairs at the Comedy Cellar (or saw glimpses of it on Louie), but this was the most fleshed-out picture of its mythic quality that I’ve ever seen. Though Crashing seeks to be another Apatow-ian grounded comedy — Girls was a frequently cited influence, says Holmes — it also seems like it will provide a remarkably specific, authentic portrayal of the stand-up world.

In the show, Holmes plays a version of himself when he was first starting out in comedy. As in real life, his wife’s cheating becomes a catalyst for him to dive deeper into stand-up while he’s stuck sleeping on acquaintances’ couches. Those days are long gone for the actual Holmes, who, besides his HBO series premiering on February 12, has a wildly popular podcast (You Made It Weird), and a new stand-up special (Faces & Sounds) premiering on HBO this Saturday, December 3.

During their break for lunch, Holmes and Apatow sat down with me at the Olive Tree Café, the restaurant above the Comedy Cellar with the aforementioned table, to discuss Crashing, stand-up, and what they each bring to their partnership. A few months later, I spoke again with Holmes, this time alone, about his stand-up special, sex jokes, and doing comedy in Trump’s America.

What was the goal of the “comedians’ table” scene?
Pete Holmes: I did a lot of takes, actually, where I was, like, “Ah, the comedians’ table.” Just to really drive home, “Why does Pete feel weird about sitting at the table?” [Points to a nearby table.] So much of that stuff happened for real right there, at the table adjacent to the comedians’ table, which is where I would always sit.

The kids’ table of the comedians’ table.
: Exactly. I still remember the week I got Best Week Ever and Premium Blend, which were two big deals. Overnight, it went from I’m just some open-mic shitty kid to Big Jay [Oakerson] saying to Bill Burr, “Fuck off, Burr, he’s got more credits than you now.” And I was just, like, Please don’t include me in this. I don’t wanna say anything!

Why focus on comedians?
Judd Apatow: I like writing for people who are playing comedians, because comedians try to be funny. You can be very real and organic and be funny because they’re attempting to be funny all the time. That was what we had at Larry Sanders, as everyone in that office was making jokes because that’s how they communicated. Still, the idea that they’re comedians isn’t even the primary aspect. They’re the type of people that are interested in talking about their problems and their point of view.

What do you like specifically about these stories of comedians starting out? You’ve done Funny People, now Crashing, and Kumail Nanjiani’s upcoming movie.
: Crashing is about open mic-ers and people who aren’t good yet, which I don’t think I’ve ever seen handled as deeply as this. It’s an interesting world of people who are trying to escape real work by doing something like this, and yet you have to suffer so much to get good at it. It is like if you wanted to be a professional ballet dancer and it was you just spinning in your room alone.

But not even alone! You’re spinning in a room in front of an audience expecting you to be a professional ballet dancer.
: That’s what I think is so great about it. It reminds me of watching Trump give multiple speeches a day. The entire crowd is in a rage and laughs at anything he says. As a result of getting laughs, he actually thinks he’s good at it. He thinks his ideas are good, because a very specific subset of the culture appreciates his point of view, so then he reveals even more of his crazy, because he thinks he’s killing!

How do you perform stand-up badly, Pete?
: That’s a Judd thing, man. You just do it over and over —

JA: Until the crowd gets bored. The audience is always supposed to think he has promise. We want the jokes to be decent, but he’s just not in a groove to perform that well. That’s been fun, but it’s also very sad for Pete because sometimes he’ll do jokes, which get an applause break when he goes on the road, but here the same exact joke will get nothing.

PH: Nothing!

JA: [Laughs.]

PH: It’s made me realize I don’t have the grit to start over. If I had to do this now, I would quit. Like when we do a fake open mic — if it’s only seven people, there’s only so well you can do. It hurts, even though it’s pretend.

JA: There’s nothing funnier than when you do a set and it doesn’t even go badly, it just doesn’t go as well as you want it to go. Say it’s not a ten; it’s a six. You feel bad in your soul because you’re sharing something and the audience is saying, Nah, don’t share that.

How did you start this project together?
: Pete’s manager is my friend Dave Rath, who actually ran one of the first [alt-comedy] rooms in L.A., the Diamond Club, and worked at the Improv when I was doing a lot of stand-up there in like 1990. He said, “Hey, will you do Pete Holmes’s podcasts?” And I said, “Who’s Pete Holmes?”

PH: [Laughs.]

JA: He said, “Just do it as a favor.” The other two guests were Kumail and Chris Gethard. And now I’m working with all three of them. Also, I did a sketch for Pete’s talk show where he pitched [Crashing] to me as part of the sketch and I said it was too sad. Then we totally realized maybe it wasn’t too sad.

PH: [Laughs.]

JA: It was properly sad.

PH: Just sad enough.

Pete, what was it like to be courting Judd Apatow?
: It was spread out with months and months in between. Fortunately I was working on the talk show, so that kept me from hounding him. I came out to the Trainwreck set to pitch it, and now, having hung out with him, sometimes I trip out on how fortunate I was. You always have energy to do things, but you had energy and availability and an interest.

JA: That’s only because I didn’t think it would happen.

PH: Judd will be like, “Yeah, sure. Write it.” And then I was like, “Okay. Let’s do it!” I was so eager to work with him. It was very natural and easy. Judd is just like any of us. We’re both comedians, we’re both comedy nerds. For as busy as he is, his fingerprints are on every part of this.

Judd Apatow, Pete Holmes, Artie Lange.

How much of Pete’s religion stuff is in the show?
: Judd’s very good at being like, “At the end of the day, it’s really funny.” If I get to sneak in something about having a fuller understanding of the divine, that’s a bonus, but I don’t think that’s the agenda of the show. Sarah Silverman just did a lovely scene where we talk about God, but it’s mostly a slow, real, funny moment. There are little Ram Dass Easter eggs in there. Like in the pilot, George [Basil, who plays the man Pete’s wife cheats with] says, “This is all grist for the mill,” which is the name of my favorite Ram Dass book. That’s also the perspective he’s representing. If you’re a big fan, you’ll catch those points, and if not, you see George’s dick three times.

[Editor’s note: The rest of this interview took place in November.]

When we last talked, Judd said something that Marc Maron often says, which is that a comedian is a person who can make all audiences laugh. Do you agree with that?
: I don’t want to be divisive — though I agree with them on one hand, I disagree on another. I’ve done so many shows where the age range is off. Like, I’d have a very strong feeling they don’t know the difference between The Hobbit and the Lord of the Rings movies. In those situations, the comedian really has a choice to make: Do you want to please a large amount of people by dropping some of those references, or do you want to really dig in and say, “Hey, I’m me all of the time?” And it’s not just references. The themes and ideas that I explore are always the themes and ideas that I’m going to explore. If you can do that, if you can find that courage — and make no mistake, that is an act of courage — to not just give them what you think they want, but rather make them want what you have to give, you’ll find all of these older people who do know The Hobbit reference or do struggle with being single. Those people can be very moved and becomes fans for life because you played at the height of your intelligence rather than giving them what you think they wanted.

After watching the trailer for Crashing, a co-worker pointed out that your wife cheating on you is appropriate in the age of the cuck.
: [Laughs.] There’s something really interesting with starting a show in a position where you’re a victim. I could see someone being like, Oh, this is just another show about a man getting punched in the balls and losing his agency. But sometimes that’s what wakes us up. Pete never would’ve asked for this, but it becomes a low-grade fuel that he can run the machine on. You find strength in weakness. This is what all the mystics are pointing us to. You find life in death, you find joy in misery. The show is a tip of the hat to suffering.

How much is your philosophical thinking about the show actually involved in the writing?
: I would say not really involved at all. That side of me is the song I’m trying to keep in my head that subconsciously affects my behavior. Like, you might be a little bit more friendly or smiley if you have “Walking on Sunshine” stuck in your head. Similarly, if I am writing a script, the rest of the day I was probably listening to Ram Dass. I was probably reading Joseph Campbell. Steve Martin has a quote: “The subconscious brain writes, the conscious brain edits.”

Let’s talk about the HBO special. I wanted to ask about the “Why are they called unicorns? The should be called unihorns” joke. Where did that come from? I enjoy it, but it is also a dumb joke.
: Jimmy Kimmel watched the special and that’s the joke that he was drawn to, too. Part of the joke is to point out how silly the joke is. Science would like to tell us that people laugh because of the benign violation theory, but comedy doesn’t have hard rules. There’s always an X factor. It’s silly. It’s playful. The special has all these bits I’m particularly fond of, like the one about how men don’t always want to have sex — stuff that I’ve worked on and polished and wrote and rewrote and took notes from friends. And then there’s unicorn, a joke I wrote 15 years ago. It’s an invitation to not take this seriously.

You’ve ended both of your specials with your sex material. Is that deliberate?
: Most comedians will do their sex stuff at the end because you can’t follow your own sex stuff. We’ve all made the mistake. It throws the set off. A shitting-your-pants story. A jerking-off story. Fucking. Porn. Even if you’re out there and doing what I’m doing — which is saying that you don’t like pornography — people still can’t help perking up a little bit. Though, now I’ll take it as a personal challenge to not close with a sex joke. I’m going open with the sex stuff.

Have you done stand-up since the election?
: I did stand-up two days after the election. In Ohio. I didn’t even know it was a red state until that week because that’s how apolitical I am. I don’t say that to be glib — I just haven’t followed politics my whole life. Now I follow them more closely because they seem so much more impending. So this felt like the universe winking at me: You’ve been alternating between throwing up and crying for two days. Now get on a plane and fly to what in your perverse imagination will be people with pitchforks, mad that these L.A. lefties have come. But then I got there and everyone in the Chipotle seemed pretty normal. People weren’t eating babies. Oh, that guy’s drinking coffee. I guess we’re still drinking coffee. You sort of piece the world back together and see that the air isn’t on fire.

My approach was, has been, and will continue to be, whether I’m in Ohio or L.A., “Times are tight, things are tense, I need to laugh.” Just a little disclaimer up top that says, I know what you know. I’m not burying my head in the sand. I’m sitting shiva with the people who are suffering as well, but for fuck’s sake, can we please just listen to some jokes for a little bit? I see what happens when you don’t laugh, when you go inside and the anxiety and the dread and the panic get the floor. They shouldn’t be able to steer the car all 24 hours of the day.

I remember when George W. was in office and people were having similar levels of panic. Stand-up was important to inform us: Did you see what he did, hear what he said? With Trump, it’s like, Yes, we know what he did! We know what he said! Everyone knows. And for the love of Christ, can you entertain me for ten minutes? I did a show in L.A. and I was like, “You know what, this isn’t the time when people are not informed.” I killed harder than I’ve killed in a while. Every laugh had that extra we need this. I’m up there and I’m laughing too. I needed it too. It’s not that I begrudge other people for talking about it, but at a certain point, it’s not reprehensible to say, Let’s just put it aside for 15 minutes. Literally, it’ll be there when we’re done. I promise you. We can have a more serious conversation later. But for now, can I just tell you about flight suits and my dog?

This interview has been edited and condensed. 

Pete Holmes and Judd Apatow on Crashing, Stand-up