Owen Benjamin‘s new special, which debuts on Comedy Central tonight and comes out in a combined CD/DVD package on July 2, finds him walking the streets of Austin, Texas, high-fiving strangers. It’s the opening for “High Five Til It Hurts.”

Why Austin?

“It’s such a cool city. It’s the combination of middle America and the coast at the same time. Chicago has that quality, too,” Benjamin told The Comic’s Comic this week. “I like the coastal open-mindedness, and the values of middle America.”

Then, picking a venue to record the special means finding just the right combination of elements, too. “For me, it’s very specific things that anywhere can have. I like when the crowds are really dark. And sitting close together. Not too cold. Things like that. when I go up after 25 minutes of opener, it’s a perfect amount. When it’s like that, it can be anywhere. Any crowd can be good. They’re sitting closely together. They’re not bright. I’m bright. It’s all good.”

Any size crowd, though?

“Best range is 400 to 1,000 is perfect. Over 1,000, you start losing the intimacy a little bit,” Benjamin said. “So yeah, that’s the dream. 400 to 1000.”

Seems like you’ve put some thought into the particulars of staging stand-up.

“There’s not really much else I think about,” he said.

Onstage, that’s another matter, entirely. In “High Five Til It Hurts,” Benjamin jokes that he, like most guys, will spend an inordinate amount of time talking about and thinking about their penises. In the track, “9 Dicks,” he goes into great detail about it. And spoiler alert: He wouldn’t keep all nine. If that seems wrong or violent to you, as it might have to me, I asked him. As he explained to me: “You don’t really cut off the dick. I’m not talking about a violent scissor-type situation. More like a Mr. Potato Head situation. Simple removal. Not a vicious dick cut.”

So there’s that.

To a more relevant subject, then.

Benjamin’s father, as he also explains in this hour, is a professor who teaches rhetoric. How much did that part of his upbringing impact his decision to pursue a life onstage and in stand-up comedy? “He taught rhetoric. Upton Sinclair. Political discourse and all that stuff. Persuasion. Debate. I feel like propaganda is the bad word for it, rhetoric is the good word for it,” Benjamin said. His father’s impact on his career choice, he said, was “huge” and contributed to his lack of fear of public speaking.

“I wasn’t even the funniest friend growing up, and I didn’t have that many friends. Just going onstage without and fear,” he said. “As a comedian, you’re trying to persuade the audience to laugh. A laugh is someone physically relating. I’m basically a salesman of comedy. I get that from my dad. He’s taught people on SportsCenter how to sell anything. How to sell a line.”

The other thing you’ll notice about Benjamin is his musical acumen. He may wait 40 minutes into his hourlong set to go to the piano. But not long after he asks the audience, “You guys want to hear some music?!” you’ll be glad that his question was rhetorical.

Here is a bit from the special, from the track “Music/Timbaland,” in which Benjamin jokes about the musical talents of our current hip-hop hitmakers.

What was your musical training? “I had a really good piano teacher growing up,” Benjamin said. “My dad sang opera. We didn’t have TV growing up. I would just watch my dad play and think it was cool.”

How old were you when you started? “I was 2. I started really really young. I think I have 5 percent Asperger’s or OCD, where I can do the same thing every day. That’s why I’m so glad I don’t do drugs. Because I would do the same thing all day. I could play the same song for hours. I find repetition to be comforting instead of annoying.”

When he was 10, Benjamin saw Adam Sandler perform. That helped tip him even more toward musical comedy. In his earlier years as a stand-up, Benjamin opened for Julio Iglesias on the road in concert. He mentions that in “High Five Til It Hurts.” Benjamin also toured with Jimmy Fallon in the year before Fallon jumped into late-night TV with Late Night, and followed that up with a year performing musical bits for Jay Leno during Leno’s brief stint in primetime on NBC. And now, Benjamin is in primetime on TBS (Conan’s channel), as part of the cast of Sullivan and Son.

So Benjamin has a bit of insight into the late-night machinations.

“I just feel like there’s plenty of chiefs for all the mics,” Benjamin said. “They’re all just such good dudes. For what we’re paid and what we do. And they’re paid 1,000 times more than I am. We’re all so fortunate.
There’s no reason to have beef with anyone. The only time I’ve had beef with anyone is if they personally offended me.”

“Leno just gets thrown under the bus. He’s such a nice guy. They treat him like he’s Nickelback. He revolutionized comedy. He opened for Miles Davis before that was a thing. He started that. He killed to have his own show on television. A lot of people don’t have respect for their elders. It’s cool what he’s done. And his ratings speak for themselves. I know I’m on TBS, but I don’t really know Conan at all. But Jimmy’s going to do a great job on The Tonight Show.”

Benjamin has spent much of his more recent time on set and on the road with his comedy cohorts on the TBS sitcom, Sullivan and Son. Fronted by Steve Byrne, the show also features stand-ups Ahmed Ahmed and Roy Wood Jr., in addition to Benjamin — and for the past two years, has sent all four of them on tour together to comedy clubs and theaters.

What’s that been like?

“It’s the closest thing a comedian can get to to being in a boy band,” Benjamin said. “We also bicker sometimes. The brother bickering. But it feels like a summer camp that never ends. It’s really really fun. We work hard. We usually put in an 80-hour week. Steve passed us because he knew we’d all get along. And they’re all so funny. There’s no real weak link on our show. If one of us sucked, that would suck.”

What’s Benjamin’s role in this boy band of comedy, then? “My part? At 33, I’m still the youngest, so I’m the baby in the boy band. I don’t know! I’m probably the most simpleminded.”

And the other guys? “Steve’s the leader. He’s our McCartney. We do what he says. His plans have all worked out to our huge benefit. Listening to Steve six years ago is the reason I’m a homeowner now. Roy just goes with the flow. And Ahmed. He’s always raging with someone at the TSA, so we never see him.”

The DVD includes bonus material, including his half-hour Comedy Central Presents from a few years ago, and a series of “Jokes From…” that finds him vlogging from wherever he may be. A U.S. Army base in the Middle East. A tunnel near Chattanooga.

Here’s the bit he does from the desert.

“I didn’t get to do enough of those,” Benjamin told The Comic’s Comic. “I wanted to do 100 of them. I travel so much. I thought it’d be funny to do premises from a remote spot. And not even try to get an audience. Just jokes from a Ferris Wheel or a plane…why not let the environment be the joke.”

So. So not the meticulous planning for your 400-1,000 seat, properly lit venue for the special.

“It’s actually the exact opposite. It’s no people. I was trying to make it work.”

You can find Owen Benjamin performing live on tour this summer with the cast of Sullivan & Son.

Owen Benjamin: High Five Til It Hurts, premieres tonight on Comedy Central. It’s available July 2, 2013, on CD/DVD, and via iTunes, Amazon, Xbox, Sony and Vudu.