When Pete Holmes’ late-night TBS show was canceled in 2014, he turned to one of his writers: “Are we supposed to get drunk?” he asked. “Is that what we do?”

In the end, the Lexington, Mass.-born stand-up chose other coping mechanisms. Holmes, 37, plugged away on his popular You Made It Weird podcast and fiddled with an idea for a new TV series. With the help of producer Judd Apatow, the latter became HBO’s Crashing, a forthcoming semi-autobiographical half-hour centered on a young comic whose wife leaves him, forcing him to crash on acquaintances’ couches.

You first pitched a version of Crashing to Judd Apatow while working with him on a Pete Holmes Show sketch. How long was it brewing?

Judd and I were improvising in that sketch and he was kind of messing with me to be funny. He was like, “No really, what’s your idea? No really.” He kept encouraging me to throw away the script and tell him my life story. So I told him about growing up religious [Christian], and then my wife left me and then I got kicked into the deep end of the New York comedy scene. He was like, “That’s far too sad, [people] won’t want to watch that.” The official pitch [for Crashing] happened a lot later, and I [went to him because] it’s his kind of show. It’s got bromance, and he loves the camaraderie of comedians and coming-of-age stories, and I was a bit like Steve Carell in The 40-Year-Old Virgin. He was just like, “Well, write it.” So, I wrote and sent him five episodes He would read one and he’d say, “This is great, write another!” and then I’d do another and then he’d read the next one and he’d say, “This is great, do another.” Honestly, I jumped at the opportunity to impress him, but it really ended up fleshing out the show.

Why else do you think that you specifically wanted to do a scripted series rather than another talk show or a sketch show? This idea could even be an independent film.

Another reason I went to Judd is because I love Girls. These shows that are like me in a way, emotionally and tonally. We’re not just trying to create a perfect comedy like 30 Rock where every two seconds is an amazing Ivy League-level joke. We’re going for some serious heart and warmth, and we want you to care about the characters much like you do on Girls.

How did the demise of the late-night show prepare you for what came next?

In a pressure-cooker style, the talk show taught me who I was as a comedian even more than touring and doing sets do. Something that I liked doing on the talk show was finding those ways to be super-personal. I was always inspired by the way that David Letterman would call his mom. I wish people could rewatch it because they would see me working through my psychology, working through my relationships, working through whatever it may be. But I carried my love of merging with a guest into Crashing. I like to think it’s 1 percent a talk show in that every episode I get an opportunity to bounce off a different guest star and adapt and shift to best suit them. In the pilot, it’s Artie Lange, and when I’m with him, I’m more scared and quiet. When I’m with Sarah Silverman [in another episode], I’m more silly.

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It was personal and had your name on it. How much harder did that make it when it failed?

I think it was Mike Birbiglia who was like, “You might not want to call it The Pete Holmes Show because when it’s canceled, it will say ‘Pete Holmes Canceled.’ ” But I didn’t mind. There was no press that it was canceled, just in the way that there was no press [when it was on]. Even while it was happening, I was like, “Oh, we’re like The Ben Stiller Show; people will appreciate us later.” I thought we’d stay on the air and live to see that appreciation. The new regime at TBS [under Kevin Reilly] is like, “Oh, you would have done well the way that we’re running the network now.” I’d love to see it come on to some streaming platform so that people can watch it because I’m very proud of it, but it feels more like a secret club that I was in than a TV show.

How did you process the news and ultimately move on?

Oren Brimer [who worked on The Pete Holmes Show and now Crashing] came over, and I remember saying to him, “Are we supposed to get drunk? Is that what we do?” Instead, we started talking about what would be next because we were at Olympic levels of comedy. The Olympics were over but we were still in incredible shape, and we were so used to getting up every day and creating something. We went out and tried to pitch a sketch show [first], and that’s when I had the idea for [Crashing].

How does the runup and heavy promotion for Crashing differ from your TBS experience?

It feels really, really great. I don’t want to put down TBS, but we were a low-budget operation, and [the show] was made weeks ahead of time so we couldn’t have [big stars] on promoting things — not that we could even get those people. It was like the island of misfit toys. In the pilot of The Pete Holmes Show, I say “f—” several times in the monologue and it’s unbleeped! And I took that as a sign, “Oh, no one’s watching.” We didn’t have meetings about the ratings. We didn’t get notes, we were just f—ing around. It was super-fun but all the while, we were like, “I kind of wish more people would see us.” Now that I’m at HBO, I just saw someone Instagram a beer mug in Brooklyn that had “Crashing” on it and I was like, “This is what I’m talking about!” If you’re proud of something, which I am, you want people to see it.

How different is it now when you go on other talk shows and you’re a guest?

It is interesting. I catch myself simultaneously being a guest and evaluating the host. I might have done this or this. I guess it’s like when chefs hang out and these guys are master chefs — it’s like I had a food truck for a little while but at least I know how to move the burners and the knives so when I go on Kimmel and he kills it, I’m in a unique position to appreciate how hard it is having done it a little bit myself. 

A version of this story first appeared in the Feb. 24 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.