Big Jay Oakerson Is a Comfortable Dude

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The New York Times deemed Big Jay Oakerson the “master of the dirty joke,” a title he lives up to in his new Comedy Central special Live At Webster Hall. Premiering this past weekend, the hour is classic Oakerson — a loose blend of crowd work, storytelling and dick jokes, and occasionally all three at once.

Oakerson, a Philly native and longtime staple of New York City’s club scene, has had a busy year. His Seeso crowd work series What’s Your F@#king Deal recently wrapped up its first season; he’s almost a year deep into The Bonfire, the twice-weekly radio show he hosts with Dan Soder; and his podcast Legion of Skanks produced its first-ever anti-comedy festival, Skankfest, this past weekend in NYC. I recently chatted with Oakerson about about “Live At Webster Hall,” developing material, and staying comfortable in the face of an uncomfortable audience.

So the special comes out Saturday. You got plans to watch it?

Yeah, we’re having a party. I’m one of three parts of a podcast that’s putting together a comedy festival in Long Island City — it’s gonna be at ten o’clock Friday and we’re showing the special at midnight.

Have you seen it already? Were you involved in the editing process?

Very little. I hate staring at myself on the screen — I feel awful about myself, looking at myself. I’m happy with the content so I try not to watch as much as possible.

You perform on a number of very different platforms — clubs, radio, the podcast. Do you work out most of your jokes in the moment? What’s your process for developing material?

The special was good because I’m so blue that I don’t do too much TV stuff, and I’ve been able to stockpile my better jokes. So I had some heavy-hitting jokes just waiting in the arsenal. But everything else comes through working the crowd, remembering a story — I try to keep it as organic as possible. This was probably the most structured I’ve been in a long time because it was a special. But what’s cool about Comedy Central is they really did give me the reins to let me play as I wanted. That’s why I’m so proud of the work; there’s a little bit of talking the crowd, using them, off-the-cuff stuff, things I said onstage that I’ve never said since or before in that special. It’s a real nice capture of a moment in time.

When I talked to Dan Soder about his special a couple weeks ago, he said you guys pretty much prepare for The Bonfire by getting high, talking to each other, and saying, “Wait — save that story for the show.” Does that casual approach hold true outside of the radio show?

Yeah, what I tend to do is develop a bit or two and keep it in the pocket. And for a couple weeks around the city, I try to eke in two or three new things I have, just to keep those strong. And then once I’ve cracked what I like, I’ll just sort of back-pocket them.  When I go on the road and headline, I’ll throw in new stuff there. My drawing board’s kind of just going up cold with no real plan, and seeing if I can come up with funny stuff out of that. It’s born from crowd work and just talking to certain people. Sometimes it’s lightning in a bottle. Sometimes there’s things you’ll say one time and it kills, then I try it two or three more times and it doesn’t hit so hard. And I’m like, “I guess it was just that moment, with the people who were there.” But a lot of times you’re able to craft it and mold it around.

Is it hard to let go when a thing doesn’t work, those second or third times?

No, I don’t think so. For me, the most fun about being funny at all is just being funny. Not like telling a joke that I wrote — to me it’s more fun to be like, “Hey, I’m a funny guy, you guys are probably some weird people, let’s just see where it goes.”

The New York Times called you the master of the dirty joke. Have you had any experiences where a joke just totally didn’t work and you had to dig yourself out?

Through time I’ve had plenty of bad ones. That almost kind of goes back to my time of being married to a set, doing jokes and not having that confidence — if it’s going bad or if something doesn’t hit, I’m like “okay, I guess just tell another joke.”

The beauty of what I do now is there’s definitely jokes that don’t hit or go sour. It’s uncomfortable. I think it’s a matter of owning that comfort. The person who wins is generally the person who stays the most comfortable. If somebody in the audience is turning on you, it’s easy just to make them just as uncomfortable by asking, like, “What happened there? What’d you guys not get? What’d you guys not get about the joke? Do you think I’m being a genuine racist, do you think I’m being a genuine misogynist?” And you kind of pull the curtain on that stuff and it reaffirms what everybody’s roles are here, and they tend to fall in line.

How has your perspective changed as you’ve been raising your daughter? Does she influence the way you write or tell jokes?

No. I try not to hide her from it too too much, but I do try to keep her away from a lot of it. The radio show especially is so accessible to her. I’ll be telling some pretty foul stories or some embarrassing whatever, things I would not want her necessarily to know — a 13-year-old doesn’t necessarily need to that I smoke weed, she doesn’t need to know some of the sexual things I’ve been involved in. Every now and then I’ll get off the show and she’ll just send me a picture of the screen in the car — it says “The Bonfire” — and I’m like “Ah shit, she was listening to that.” And I end up having an argument with her mom, telling me the show is not for her demographic.

Where do you feel most at home as a comedian? In a club, on a podcast, on the radio? Is it all the same?

I feel very at home onstage, for sure. I feel very comfortable onstage in front of an audience. I think radio — and podcasting too — is a different beast in a weird way. I can’t put my finger on what it is. Maybe it’s the production of it, the way it runs, with sound effects and accessible music and video content, all these things that make it run. Me and Dan Soder, our only job seems to be to just have fun with each other. You asked about preparation — we go to a radio show with a subtle plan in mind, “We gotta talk about this,” but I’d say eight out of ten times we keep teasing that we’re gonna talk about a subject that we never even get to. Because of some silly thing. We did this show yesterday from across the country — I’m in LA right now, Dan’s back in New York — so I go into the studio here, I can hear them all in my headphones, and we had some things to talk about. But he ends up telling me in the first minute that he met Jason Mraz, and that he was a really nice, mellow guy. Which is a funny thing; I assumed that the guy who plays ukulele music is gonna be pretty mellow. And then we started making up a bunch of fake rumors about Jason Mraz being a terrible person, and then all the callers started calling in and tagging onto that, and we did two hours just ganging up on Jason Mraz. We never even got to the subjects we were going to talk about that.

Is that a common thing when you’re doing crowd work — suddenly it’s ten minutes later and you haven’t gotten to the jokes in your pocket?

Oh yeah, that happens very often. And then sometimes the first thing I say off the cuff, the crowd’s not onboard with it, and I’m like, “Okay, guess I’ll try a joke.”

So you’ve got the radio show, the podcast, your Seeso show, and the special. Is there anything else on the horizon?

Hopefully we’re gonna get a second season of the Seeso show. Hopefully Oddball tours this year and I can get on that. And then just trying to grind out and get ready for hopefully another hour special in a year or so. I’m just happy to be out on the road, it’s a different experience now that audiences tend to be mostly fans. I’m not just relying on people hopefully showing up to see a comedy show, there’s actually people making it a destination event. That’s new to me, in all the years I’ve been doing comedy. So I hope the special kind of moves the needle more in that direction.

Does that phenomenon — having mostly fans at your shows — make you more comfortable, or does it make you nervous that you have to live up to some expectation?

It makes me comfortable. I’m fine to, like, abandon jokes. With my style of comedy, you usually have to win over some of the crowd. But now most people come out to the shows — if there isn’t a rare person who has some objection to what I’m saying, or stands up or heckles — the crowd’s pretty behind me. There’s no process of having to win them over, they’re mostly excited I’m going onstage. And that’s new to me, it makes it much easier. People clamor to get up front because they want me to talk to them. The only problem I’ve encountered with that is sometimes people get hammered, and when I’m trying to talk about whatever, they’re throwing in some very inside baseball references because they’ve listened to all my stuff.

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