Pete Holmes strikes back: The How We Roll star bowls down memory lane
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As Pete Holmes himself points out, he's been in many lanes throughout his career, from stand-up comedy to a talk show to an HBO dramedy to podcasts. And now, after all that, he's throwing in a multi-camera sitcom for good measure. The comedian stars in CBS' new series How We Roll (premiering Thursday at 9:30 p.m. ET/PT) as real-life bowler Tom Smallwood, who takes his shot at going pro after getting laid off from his factory job. (You can watch the series' trailer above.)
"He decides to try his hand at the only other thing he's good at, which is very similar to me with comedy," Holmes tells EW. "I hope what hooks people into the show is the feeling of that risk, when you're putting everything on the line to try and pursue a dream. Especially after the quarantine, which I think made us all go, 'What am I doing?' The fact of the matter is, it's often these things that we don't like and don't ask for that end up pushing us in the direction that we're afraid to but ultimately need to go."
As Holmes notes, it's a feeling he can relate to, as more than one of his past projects have failed to bowl people over, so to speak. Ahead of How We Roll's debut, we asked the comedian to pick three memorable rolls — er, roles — from his career: one knockout, one that fell short, and one total miss.
Strike: Crashing (HBO, 2017-2019)
Everett Collection Pete Holmes with Bill Burr and Artie Lange on 'Crashing'
"That was not just a dream, but literally the dream," Holmes says of his acclaimed, semi-autobiographical sitcom, which counted Judd Apatow as an executive producer. Crashing starred Holmes as himself, pursuing a comedy career while bouncing from couch to couch after his wife cheats on him, and featured many comedians in guest roles as themselves (such as Bill Burr, above).
As Holmes recalls, the idea for the series emerged after his TBS talk show was canceled (see below), and he found himself somewhat adrift. "My friend Oren Brimer and I were like, 'Let's go pitch a show to Comedy Central.' We decided that we would pitch a sketch show, and in the preamble to that pitch, the head of Comedy Central said, 'Well, one thing's for sure. We don't want another sketch show.' We all laughed, and we just abandoned the pitch. We acted like we were just coming in to say hello."
Riding away from that disastrous meeting, Holmes found himself thinking, " 'What would you do if you could do any job in show business?' And I was like, 'I would tell my story with Judd.' Specifically because, 40-Year-Old Virgin and all of those great movies met me at these interesting times in my life when I really needed them."
With the idea for Crashing in mind, "I flew to New York just to pitch it to [Apatow]," Holmes says. "He was shooting Trainwreck, and I got in touch with one of his producers, who said Judd had 10 minutes or something. I flew to New York to pitch on one of the sets of Trainwreck, and I think even during the meeting, he was like, 'You didn't fly out here just for this?' I was like, 'Oh, no. I have all sorts of business in New York.' But it was just for that. That was my blue-sky, anything-goes [moment], making an episodic TV show on HBO with Judd Apatow."
Split: The Pete Holmes Show (TBS, 2013-2014)
Holmes has a lot of affection for his short-lived talk show, which TBS canceled after just eight months on the air. "It's this time capsule of me before I was married and had children, while I was figuring out what it meant to be a grown-up," he explains. (Holmes divorced his first wife when he was 28, and remarried in 2017, when he was 38.) "The Pete Holmes Show was specifically the point of view of a guy looking for love and some sort of stability. So it has this really cozy, relatable quality to people that are going through that."
Not for nothing, "I think it's also probably the funniest thing I've ever done," Holmes adds. "Crashing was certainly funny, but it was almost exclusively other people being funny by design. On The Pete Holmes Show, I [did things like] sing a duet as Ray Romano with Ray Romano, which I think is still one of the funniest things I've ever done."
Alas, the show simply never found enough of an audience. "Conan [O'Brien] was a huge believer in it, and really tried to make it work," Holmes says. "It just wasn't meant to be. My joke at the time was, I completely understood, because the network could make way more money running black-and-white reruns of Big Bang Theory with no sound than a half-hour, non-topical talk show. We were taping shows months ahead of time, so we couldn't do current events, and we couldn't even really have guests promoting things. So it was just me bulls---ing with my friends."
Still, that resulted in what Holmes calls the most "funny for its own sake thing" that he's produced. "I'm really proud of it," he adds. "If you come up to me and say you love The Pete Holmes Show, there's a special place in my heart for you. Because I'm not even sure TBS knows it aired."
Gutterball: DieHard battery ads (2007)
Imagine Apple's iconic "Get a Mac" commercials, but for car batteries — and minus the "iconic" part — and you can more or less picture this failed ad campaign for Sears' DieHard brand, starring Holmes as a battery's cheerful positive terminal opposite Matt McCarthy's grouchy negative terminal.
"If you could have heard the way they talked about this campaign…" Holmes says ruefully. "They were like, 'This is the new Apple commercials.' The casting process was excruciating. I mean, 12 callbacks, chemistry tests — it was like, 'You have to have a go bag in your office, because they're not going to tell us who booked this epic campaign until the last moment, because it's that big.'"
As such, Holmes was, well, positive that he'd made it when he finally booked the commercial. "I got the call, I grabbed the bag, I went to the airport, all the while being like, 'This is it! I'm Justin Long, he's John Hodgman, and everyone is going to hear about this campaign!'" he recalls. The rest is history... or rather, it isn't.
"Whatever they were looking for to happen, didn't happen," Holmes says with a laugh. "No one has ever said, 'I love you in those Sears DieHard commercials.' The one time my mom saw them was in a Sears battery department."
Still, at least one good thing came out of it: "McCarthy and I have worked together for over 10 years; he's on How We Roll as another bowler named Carl, and he's one of my dearest friends. So in that sense, it was a huge success."
As for DieHard batteries, they eventually secured a much more memorable campaign featuring Bruce Willis as John McClane. "A happy ending for Sears DieHard," Holmes says, laughing, when told about this. "They finally found their spokesperson, because it was not me and Matt."
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