Exclusive: Pete Holmes Goes Deep on ‘Crashing’s Cancellation, That Finale, and a Potential Movie

     March 10, 2019

45 minutes before I was due to interview Pete Holmes about the Season 3 finale of his HBO series Crashing, news hit that the show was cancelled. HBO would not be bringing the charming half-hour comedy back for a fourth season. This was unexpected to say the least, and admittedly threw me for a loop. I was all primed and ready to dig into that excellent finale episode and John Mulaney’s involvement, and how Holmes and his team crafted the show’s best season yet, and now I was sitting here wondering what kind of mood Holmes would be in, or if the interview would even still happen.

It did, and it turned out to be one of the more engaging and inspiring interviews I’ve had the pleasure of conducting—given the circumstances, of course. Obviously both Holmes and myself would have preferred to see the show continue (he reveals they had already mapped out an outline of Season 4), but the comedian, writer, podcast host, and show creator was refreshingly positive about the whole thing, expressing nothing but gratitude for the three seasons of the show he got to tell.

Of course it helps that the Season 3 finale ends on such a “finale” note that it really does work magnificently as a series finale—so much so that on set shooting the episode, Holmes says they kept accidentally referring to it as the “series finale.” Pete’s story comes full circle, and he gets a “triple win” as Holmes calls it, ending on a downright swoon-worthy final shot. It’s sad to see such a pleasant, joyful, and surprisingly cathartic show come to an end too soon—Crashing was about far more than just the misadventures of a burgeoning standup comedian, and Holmes and the show’s writers always had a knack for tapping into universal truths about life, love, and happiness. But if the show had to end abruptly, you can’t do much better than the Season 3 finale episode.

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Image via HBO

So yeah, the interview happened, and what was originally scheduled as a 15-minute chat about the finale suddenly became a 40-minute exit interview about the whole series. I am tremendously grateful to Holmes for being so open and willing to get candid about the show’s cancellation and his feelings on the series as a whole, and I do think the full interview will serve as a minor consolation to fans who are still upset about the show’s cancellation.

During our discussion, Holmes talked about the Season 4 plans they had already outlined, why the surprise series-finale nature of the final episode is fitting, the potential for the story to continue on in a Crashing movie form, and what he’d like to say to fans about the show now that it’s all over. We also dug into the finale episode specifically, including Mulaney’s involvement and getting to play with the Comeback Kid comedian’s persona, and we touched on the crafting of the third season as a whole—including why the inclusion of Kat was so personal to Holmes. We also, of course, talked about that final shot, and what Holmes foresees as the future for Pete and Ali.

Again I’d like to express gratitude to Holmes for being so open and even just willing to talk mere minutes after the cancellation went public, and as a fan of the show and Holmes’ comedy, I do hope to see him back in front of the camera soon. Check out the full interview below, which does contain spoilers for the series finale episode, “Mulaney.”

As a big fan of the show, I have to say I’m really not crazy about the fact that you weren’t picked up for Season 4.

PETE HOLMES: What if I didn’t know? What if you just told me? (Laughs)

Luckily I saw your tweets beforehand!

HOLMES: No, I appreciate that, and I’m happy to be talking to you as the first interview about it.

For three seasons, it’s been this kind of special show that’s feels, I don’t know if niche is the right word, but a show that’s been really beloved, and it was kind of neat to see the outpouring of support I’ve seen on Twitter so far today, of all the people upset over the cancellation.

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Image via HBO

HOLMES: Yeah, I don’t think niche is a bad word. I think, when you’re making a show about something that’s already niche, if you do it well, then the show itself should probably be fairly niche. If not entirely niche.

That’s fair. So did you guys already have some plans in mind for Season 4?

HOLMES: Yeah. The way that it works, for all three seasons, is before you get a pickup, there’s this bizarre Black Mirror-ish-like period where you’re writing a show that you don’t know if it will exist. Obviously, I think that’s most eerie between maybe the first and second season. As you go, you get a little bit more used to the idea that you’re like, “Oh, we’re just trying to get ahead of ourselves.” A lot of those ideas might not make it to air, but it’s always [producer] Judd [Apatow’s] style and HBO’s style, graciously, to fund us getting ourselves a little bit before the pickup.

So we had the season pretty much outlined, but I’m not just saying this to be—in fact, I’d like to be clear. I’m not saying anything that I’ll tell you during the interview to just be like the positive guy. I think people maybe expect me to be. But I really do feel that there’s something lovely about the way that it ends. Because the fourth season might have dealt with some breaks or different showbiz milestones that frankly don’t happen to most people that are in comedy. The show ending where it’s ending is a little bit more true to theme, in the sense that the show was always about what it’s like to be a regular comedian and struggling. That’s why it was called Crashing, and as I’ve joked many times, it wasn’t called Flourishing.

So there’s something kind of fitting about how it ends. Think about where he was in the first season. He was living upstate, he was not plugged into his potential, he was certainly not a part of the scene, and he wasn’t very funny. At the end of the third season, he’s funnier, he’s found better relationships, better friendships, he’s figured himself out. But he’s also become a part of the scene, and that’s what getting past at the Cellar represents.

Without sounding too lofty, I always like those finales that made people talk, that remain hot in the imagination of the viewer. With the show ending here, one of my first thoughts was, “Oh, now people will talk about, ‘What do you think happens?'” Frankly, “What do you think is gonna happen?” is how most comedians feel for most of our lives. I mean, it’s always just like, we’re going to keep being funny, we’re going to keep doing as many shows as we can, but we never really know what’s going to happen. That makes the finale a little more active than, say, taking Pete into the next phase of Hollywood, which was always interesting, and was something that I wanted to do, or was open to doing, certainly. There’s something about this finale that feels eerie in how appropriate it is for the show we were making.

I have to be honest. I finished the final episode, and then I went to Google to make sure I hadn’t missed something. I was like, “Did they announce that they were only doing three seasons?” Because it does feel like an ending. It feels like a nice sweet moment. I am so happy it ends that way, with a win for Pete, because I love this character so much. It would’ve been such a bummer if this season ended on a down note.

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Image via HBO

HOLMES: Oh, I really appreciate it. I mean, it’s a triple win. I mean, he goes up after Mulaney. A lot of times on Crashing, we do things both ways. We’d shoot maybe me doing well, and me doing poorly. Let’s say the script said that I do poorly. We might shoot one take where it goes well, just to have the option when we’re editing, just in case we want to mix it up or something. It was always scripted that Pete goes up and does well after Mulaney.

That set that I do there is something that Judd and I beated out. It seems very loose, but it was pretty scripted, maybe not the jokes, but the areas I was going to touch on were very scripted, and then I riffed around them. Judd gave me those beats, but it was not like, “Let’s also shoot him peeing his pants,” just to kind to have that. We didn’t even consider it. We were like, “He goes up after Mulaney. The table is set for it to be a disaster, and then he does really well.” Then Mulaney, who we’ve we established in two seasons now is only ever unkind to Pete, then turns on him. That’s a real phenomenon in the comedian world, when you see someone be funny, especially brazenly or bravely funny, the way Pete is, sort of making fun of John, that can make a friendship. And then he wins at the Cellar, obviously. Which, the whole season, it was one of the more orchestrated seasons that we ever did. Meaning we bookended it with a failure, and then, mirroring that failure with a success, and then, obviously, what happens with him in the last couple frames. It’s something that we don’t normally do.

I don’t know if you saw my tweet, but when we were shooting, the director is Gillian Robespierre, and we kept accidentally calling it the series finale. I mean like more than 10 times. It just kept happening, and then we’d all go, “No, no, no, it’s not the series finale,” but it’s because of exactly what you’re picking up on.

So when I found out that it wasn’t coming back, obviously the first thing you do is, you wonder how your work is going to land. How’s it going to feel in those last moments? Immediately, I was filled with the relief that I was like, “Oh, my God. It always felt like a series finale,” and then I was like, “People are gonna think that we went back and re-edited it,” which, because you already saw it, you know that we didn’t. But when you watch it, people are going to be like, “Oh, that feels like the ending.” I mean, there could be a movie or something, we’re certainly open to that. But if this were it, it would just be like, “Oh, wow. That’s nice. Thank you for that.”

It sucks that it’s not coming back, but I’ve been a fan of the show since day one, and I felt this was your strongest season yet. I loved the introduction of Kat. Even just the structure of the season, I thought, just played out really perfectly. So if you have to go out unexpectedly, I’m glad it went out this way.

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Image via HBO

HOLMES: You know, you’re really just mirroring my own feelings. When you’re a standup— Kumail Najiani and I started together, and we would go and do standup gigs, and sometimes, those gigs would be canceled. We’d get there, and there’d be no audience. When you’re starting out in comedy, one of the things that Crashing is about is that you pretend that you love standup even though you don’t yet, because you’re not good at it. I remember being outside of a club, Kumail was smoking—10 years ago, he smoked, which is really funny because he’s so fit now. But he was smoking outside the club and I was like, “I feel guilty admitting this to you,” because especially new comedians just never want to show weakness, but I was like, “I’m a little relieved that the standup show is canceled.” Kumail was like, “Yeah. Now it can’t go badly.” I was like, “Oh, that’s it! You’re right.”

So there’s sort of this feeling that the third season, we hit a stride. Obviously, the addition of Madeline Wise, which was something where I felt very close to that character, and felt very locked in writing that character with the room and with Judd and everybody. To go out this season, where I was getting the most phone calls and texts, and just running into people that I admire, and having them tell that they love the show, I was like, “That is how you go about being a cult classic.”

I think of Togetherness, for example, which was another HBO show that was short-lived. I love that show, and there’s a special warm cozy feeling you get when there’s a show that has a lifespan like this, that you found and that you appreciated.

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