Pete Holmes Is Bringing The Weird To Late Night

A crowd-pleasing comedian has become Conan O’Brien’s first apprentice. With late-night television more crowded than ever, he’s aiming to be different.

Pete Holmes stood in front of his small stage. At 6’6”, the comedian towered over the first row of audience members, whom he addressed a few feet in front of the tape that signaled where exactly he would deliver his monologue in just a few minutes.

“Sometimes, people are nervous,” Holmes told the crowd in the small studio on the Warner Bros. lot in Los Angeles, where he is taping his new TBS late-night program, The Pete Holmes Show. “We’re a new show. People are tense, nervous for me, nervous they’re gonna be made fun of or something, and nothing like that is gonna happen, so let’s all just enjoy it. You’re in a safe place.”

Soon, the 34-year-old Boston native’s soft and kind voice turned a bit more (jokingly) severe, as he expressed his concern that the show could be “pre-canceled … Maybe they’ll watch this episode today and say it’s not working; lesbian Val Kilmer is not clicking with the people.”

“You better laugh at everything I say,” Holmes continued. “In two minutes, I’m going to be on this mark and there will be cameras rolling and I’m going to be doing a monologue I’ve never done before, and if you leave me, and I’m up here and you just decide to judge me on my merit, I’ll burn down your childhood home,” he implored, his faux anger overridden by his inability to fully hold in a booming laughter.

The small studio audience, mostly high schoolers and twentysomethings, more than complied with the request, applauding at each wild assertion Holmes made in his several-minute monologue riff about farmers and daylight saving time.

After several segments, including a rant about hotel towels and a goofy interview with The Mindy Project’s Ike Barinholtz, Holmes debriefed his small team of writers and producers. Then, he met up with BuzzFeed in a small dressing room behind his set, which looks like a version of Don Draper’s second apartment that’s been filled with cartoon artwork.

It was the end of his first week of filming the show that Holmes has been anticipating since he shot three pilots in August 2012, and instead of being exhausted, the host was buzzing with energy.

The enthusiasm was par for the course for the boyish comedian, who spent years doing stand-up, as a sitcom writer, online video star, and podcaster before Conan O’Brien selected him as the host for the midnight show that follows his TBS program, a deal that was made official last February after the previous summer’s test run.

Holmes, whose first real show aired on Monday night, enters a late-night field more crowded than ever before: David Letterman has signed an extension at CBS through 2015; Jimmy Kimmel took over the 11:30 slot at ABC; Jimmy Fallon is ascending to The Tonight Show and Seth Meyers to Late Night in February; Comedy Central has added Chris Hardwick’s Midnight behind The Daily Show and Colbert Report; W. Kamau Bell is hosting Totally Biased during the 11 p.m. hour for FXX; and IFC has a cult hit in Scott Auckerman’s Comedy Bang Bang.

Holmes is well aware of the deep competition. Hell, his podcast, You Made It Weird, is hosted on Hardwick’s Nerdist network, and now they’re midnight rivals. So the question is, as Holmes asks himself rhetorically, why create yet another late-night show? Why put all that time and effort into a program that will have to swim upstream for the foreseeable future?

Because, as Holmes points out, their time slots may be similar, but his show’s content is its own strange breed. There is no desk, the monologue is one long riff and usually not all that topical, and guests — who will be pulled from his deep list of comedian friends, at least for now — aren’t coming on to plug their projects.

“The experiment is like, What if late night is really transparent and authentic?” he says. “I think a lot of shows have transparent or authentic elements, but we’re trying to upload my entire personality for enjoyment.”

As a stand-up comedian and podcaster, Holmes has made habit of putting it all out there, using his personal life — including the divorce he went through at the early age of 28 — as fodder for conversation and comedy. He plans on continuing that with the TV series, promising, “I’m not going to be telling any fake stories or representing any of the writers’ experience as my own.”

And if you’re looking to Holmes for your late-night dose of political humor, you’ve come to the wrong place.

“I don’t care that the government is shut down,” he said. “I don’t care about Obamacare’s website. I’m not proud of the fact that I’m not political, but I feel like people can have three main interests… and my three were already taken. One of them isn’t politics. I know that there are other people like me who don’t really care. So we’ll do a monologue about how I don’t know what the government shutdown means.”

Instead, he’s working at something… deeper.

“The concern is that my parents are gonna watch this show, and I hate that, I’m really looking forward to when it’s no longer novel to them and they don’t watch it,” he said, referring to his strict Christian upbringing. “It’s part of growing up religious, I’m fed up thinking that some things aren’t to be discussed or some words aren’t to be said. The podcast and now the show has been a little bit of an experiment in being like, what is a good person?”

Untethering himself from the politics of the day creates a sort of freedom for Holmes and his small writing team to play with weird and offbeat ideas, but it also restricts access to a limitless well of potential jokes. Doing stand-up, Holmes would work to hone his set, going from city to city and club to club with similar jokes, perfecting them for his specials (he has two) and late-night appearances.

Now he’s got to churn out new jokes four times a week, something he compares to an open-mic performance, or in a more zen moment, a rushing river that takes his words for eternity once he says them on stage. There is a cushion, because Holmes and his writers — many of whom, like Jamie Lee and Joe DeRosa, were his friends before the show — spent months crafting monologues before he began taping, and he’s got plenty of stand-up and podcast bits to mine too.

Holmes’ monologues and sketches are charged with the sort of absurdities and crudeness that got him the gig in the first place. (In the first episode, for example, the opener focused on weird happenings at a recent Enrique Iglesias concert.) But ultimately, should the show get extended past its initial seven-week order, finding new topics will become an impressive comedy feat.

Luckily, Holmes finds himself under the tutelage of O’Brien, who had no such safety net when he began his run on Late Night 20 years ago. Back in 2003, Holmes was attending a taping of Late Night when O’Brien waded into the crowd before the show. Holmes, still early in his stand-up career, flinched and tried to avoid the host’s line of vision, convinced that it wasn’t yet the time that they should meet. “I’m not saying I had some prophesy where I was like, We’re gonna do a show together, but it was, I’m gonna meet this guy,” he said, smiling at his hunch.

Now Holmes meets with O’Brien once a week, for pep talks and to grab whatever wisdom he can.

“Today, the conversation was that it’s never as bad as you think it is, and it’s never as good as you think it is,” Holmes explained. “So today, I feel like it’s so great, and he actually spoke to that specifically — that even if you think once that airs, everyone’s going to come to hoist me on your shoulders, well, they’re not coming. And even when you think it was terrible, a lot of people watched it and loved it, so just relax.”

Cindy Ord / Getty Images

He certainly seemed relaxed on The Pete Holmes Show stage on Friday, which, despite the O’Brien-supplied caveats, the new late-night host called the best of his first week. He’ll have to constantly be on his game too, because for all the fresh material and talk of a new approach, sheer numbers are a difficult hurdle. Leno, Letterman, and Kimmel will be in the middle of their shows when Holmes’ program begins to air. And Hardwick’s Midnight will get the benefit of Comedy Central’s outstanding Stewart-Colbert lead-in, which earns around the same number of viewers in the 18–49 key demographic as O’Brien’s audience does.

Since his move to TBS, a big part of O’Brien’s plan has been digital domination, starting with the movement of fans who were angry over his Tonight Show ouster. With many clips boasting millions of views, the host has set a template for Holmes to follow. Already, O’Brien’s new follow-up act has a number of hits with videos spoofing X-Men — Holmes plays Professor X — and he’s gained a solid following with goofs on Batman for CollegeHumor.

No doubt that Holmes will be checking the ratings, but for a stand-up comic, this is too precious and rare an opportunity to dwell on how to best appeal to the widest audience. In the comedy world, playing it safe is the worst thing you can do when you’re looking for early credibility.

“I hope it works. My gut says it’s gonna work; my fear says you should take it slow or something,” Holmes admitted. “But if the takeaway here is somebody’s taking a risk, I think that’s interesting.”

Check out more articles on BuzzFeed.com!

Facebook Conversations
          
    More News
    Now Buzzing