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Pete Holmes, star of podcasts and Chicago stand-up, takes a turn on TV

Comedian Pete Holmes

Comedian Pete Holmes

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Updated: April 14, 2014 4:49PM

When comedian Pete Holmes was 22, he and his now ex-wife wed on a Sunday and spent their would-be honeymoon driving from Boston to Chicago so Holmes could start improv classes at iO Theater (then ImprovOlympic) three days later.

That was in 2001. After six years together, they parted ways.

“My wife and I didn’t split, I don’t think, because of comedy,” says the 34-year-old Holmes, who spent three years in Chicago honing his stand-up and improv chops before moving to New York and then L.A. “But I think she probably saw that it wasn’t necessarily what she wanted. She didn’t want to be some comedian’s wife.”

With the success of his E*Trade TV commercials (Holmes voices America’s favorite stock-trading baby), his “You Made it Weird” podcast, his comedy shorts and now a new Conan O’Brien-blessed and -shepherded program on TBS — “The Pete Holmes Show,” debuting Oct. 28 — Holmes is no longer just some comedian.

“Pete is a lot younger than me and is a product of the digital age,” O’Brien told reporters last summer. “When I started doing late-night, I was covered in afterbirth. I practically learned to walk on the air. Pete is starting ahead of the game.”

If not for Holmes’ time in the Second City (the town, not the troupe), he might have charted a different course.

“I moved to Chicago because I was kind of an improv purist,” Holmes said by phone from L.A., where he’ll produce seven weeks of episodes for TBS and, ideally, wow the suits enough to earn an extension. “I had done stand-up maybe five or six times in Boston, and then I moved to Chicago to give it the old Chris Farley ‘SNL’ run.”

Upon settling into a one-bedroom apartment near the intersection of Lincoln, Damon and Irving Park, Holmes got a job waiting tables at Bennigan’s on South Michigan (the last one in Chicago, it’s closing in December) and tiptoed into the local comedy scene.

Besides iO — which he describes as “very crowded” and therefore a frustrating training ground for yet another “tall, oafy white guy that was popular in college” — Holmes joined the Playground Theater and eventually mustered enough gumption to do a few minutes of stand-up one night at the now-shuttered Lyons Den pub on West Irving Park. He kept returning and got better.

And it was there, on open-mike Mondays, he met a handful of other aspiring comics — T.J. Miller, Matt Braunger, Kyle Kinane, Kumail Nanjiani, John Roy — each of whom continues to elicit laughter for a living. Holmes and Nanjiani became particularly close.

“We used to go to Wrigleyville and try and write together, but we always just ended up talking,” Holmes says with a greatly tempered version of the unbridled loopylaugh that has become one of his trademarks. “We never really got anything done.”

On “The Pete Holmes Show,” its host hopes, there will be room to spotlight his favorite jesters — including the aforementioned group of guys he started out with in Chicago, which also includes Hannibal Buress.

Another Chicago-bred comic who is lately exploding on stage and small screen, the outspoken Buress has comically questioned the quality of Holmes’ caricature-ish Buress impression — while cyber-circulating Holmes’ caricature-ish Buress impression.

Still, Holmes says, Hannibal is high on the list of possible “TPHS” stand-up performers — if there are any. (Some elements are still in flux.)

“He’s a very talented dude,” Buress said in an email. “I listen to his podcast sometimes, and he’s an excellent interviewer, so it’s going to be great to see those skills translate to TV.”

As for the impression, it’s “average at best, but we all have our flaws.”

If he’s unsure about the inclusion of stand-up, Holmes seems more set about his show’s tone and format.

“It’s going to be less celebrity-driven and more ‘Who’s in my life that I know? Who are the people I think America should know?’ ”

Although he has no ambition to be the next Johnny Carson, Holmes does want to follow his lead in booking guests who know him well enough to mock his foibles just as insult comic Don Rickles mocked Carson’s. Playfully, of course.

“Kumail can make fun of me and make fun of my divorce and make fun of my weird beliefs, or whatever it is, because he knows me,” Holmes says. “It’s not trying to manufacture a relationship with Shia Labeouf. There’s nothing wrong with that. But there’s just a lot of shows that do that very well, and we’re going to try and do something a little bit different.”


Twitter: @MikeTScribe

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