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Jay Oakerson interview: 'I’ve had people say I’m trying to be shocking, but it’s just what I happen to find funny'

Audience members take it on the chin at the improvisational stand-up show What’s Your Fucking Deal?

Photograph: Beatrice LaBarge
Big Jay Oakerson
Working a crowd comes naturally to stand-up Jay Oakerson: He’s curious, incredibly quick and loves uncovering strange things about the lives of his audience members. He also likes messing with people. That’s why What’s Your Fucking Deal?—his periodic showcase of comics doing only improvisational crowd work, which premiered at the Just for Laughs festival in Montreal last year—works so well. Oakerson, who recently recorded an album of completely off-the-cuff material, talked with us before Deal hits the Comedy Cellar at the Village Underground on Tuesday 22.

What do you look for when you want to talk to an audience member?
The person who seems like they’re not enjoying it. The intentions of stand-up comedy are so pure: I want everyone to laugh and be happy. So when someone’s upset in the audience, I’m so taken by that. I’m very dirty, and I’ve had people say that I’m trying to be shocking, but it’s just what I happen to find funny. If you’re going to focus on the fact that I said pussy instead of vagina, I can’t help you.

Other than just not doing scripted material, what’s the hardest thing for comics to grasp when they do What’s Your Fucking Deal?

People get panicky about the crowd not being fresh. They always ask, “Can I go early?” Even a veteran like Colin Quinn—he asked to go first. I know the concern: If I go fifth, the front two rows have already [been asked], “Where are you from? Where do you work? Where do you live?” But how could you learn everything about one person in eight minutes? You couldn’t learn everything about them if eight comics did eight minutes. Alright, this guy is a plumber, this is his wife of 25 years, he seems like he’s super in love. You could be the 50th comic onstage, and I’ll bet no one’s asked them, “Twenty-five years of marriage­—have you ever put your fist up this guy’s ass?”

What do you like most about doing this show?
It’s almost like pulling back the curtain and seeing the purest, rawest thing about comics. You see their personality come through without that 10 percent actor in all of us, like, “Here’s a thought I just had, everybody…for the 50th time this week.” Dave Attell, he seems off-the-cuff, but he’s so calculated. I know Dave from taking nine-hour car rides to Virginia Beach, so I want the crowd to see that. When Paul Mercurio did it, he ran through the audience like Morton Downey Jr., which was a fun take on it. Jerrod Carmichael focused in on one guy. The guy had an ex and [Carmichael] asked him, “Why is she your ex-wife?” and the guy said, “Because she got too fat.” And Jerrod spent his whole set one-man-showing this conversation where you break up with your wife because she’s fat.

How should an audience member prepare?
You want to be playful and be willing to have some back-and-forth. I don’t want people calling out, necessarily, but if you want to be called on, you can get in a position to be called on.

And for anyone who comes to make trouble?
If there’s someone being a dick, I want a shot at him.

What’s Your Fucking Deal?happens Tue 22 at the Comedy Cellar at the Village Underground.