Turning the Show Around with Big Jay Oakerson

Every time I’ve seen Big Jay Oakerson, I’ve seen a different (but always hilarious) act. He’s certainly not alone in the growing genre of comedy based almost entirely on crowd work, but he does particularly define why it has become so popular.

We listen to comedians like Mike Birbiglia to hear a funny, intricate story, comedians like Louis CK to hear brilliant takes on simple opinions, and comedians like Steven Wright to hear how absurd our world can be when jumbled up and rearranged. We listen to comedians like Big Jay Oakerson to remember that humor isn’t always something rehearsed: at its core, humor is just part of your surroundings.

Oakerson’s podcast Legion of Skanks is a testament to Oakerson’s organic ability to be funny on any topic. His upcoming album, The Crowd Work Sessions: What’s Your F@!?#ng Deal?! (out November 17th), promises to be another hour of off-the-cuff, homegrown wit that can catch even the most refined sensibilities off-guard. I had the chance to talk with Oakerson about Legion of Skanks, the new album, and how he developed his confidence onstage.

So I just want to start by letting you know that I love Legion of Skanks. There’s never a bad moment! You, Dave Smith, and Luis J. Gomez all have such a great dynamic. Is there a lot of preparation that goes into that? Or is that all just organic?

It’s mostly organic. The day before, we usually figure out what we’re gonna do and we figure out what we’re going to talk about. It ends up being as simple as maybe a test, like when the Jennifer Lawrence pictures came out, we were like, “Well, there’s our topic.” We just go, “Who do we have? What do we have? All those pictures… who would be the pervert who would have them all?” So we go to him. That’s how we decide.

Where did the name for that podcast come from, by the way?

The name came from my ex-wife. She was arguing with me when Luis was at my house, and we were heading to the city to go do comedy shows and she was yelling at me and accusing me of running off to be with other women and seeing other women. I was like “Fuck this, I’ve got to go to work, I’m leaving.” As I’m walking out, she goes, “Yeah, run off! Go run off to your ‘Legion of Skanks’.” I thought, “That’d be a great name for a band.” Then when guitar hero came out, me and Luis played together and that was our band name. We’ve just always branded everything we’ve did as “Legion of Skanks.”

So you have your ex-wife to thank.

Yeah, she’ll sue me one day.

You mentioned in an older interview that you were interested in possibly making a TV show called Legion of Skanks. Are there any plans to revive that or anything? Would it be based on the podcast?

We wrote a script for a pilot called Legion of Skanks. Once things are in place to make that happen, absolutely. I’ll take it again to Comedy Central. Me and Dan Soder are getting ready to start on a live daily radio show on SiriusXM, on Comedy Central radio, so hopefully the Comedy Central family keeps taking my ideas.

And you produced your last album, An American Storyteller, through Comedy Central records, right? Was it sort of the same experience this time around or has six years brought a lot of big changes?

I think I have more people anticipating it this time. The last time I released an album was 2008, and nobody really knew who I was. No one was really clamoring for it, so I think it will sell pretty well out of the gate. Especially since it was a crowd work CD, there was no material on it. It was all off the cuff and it was fun and hopefully people enjoy it.

Do you find that it’s harder to record your style of comedy? So much of what is great about watching you perform is that you’re so in the moment.

I thought it would be hard to capture, but from everyone I’ve had listen to it so far I’ve gotten good responses – and I’m the worst critic of myself. I’ll listen to it once, say it’s okay, and the next time I hear it I’ll say that it stinks. But that’s just my own horseshit. I thought it would be difficult. I didn’t know if it would actually be something that would work. I listened to it and the first few times I did laugh.

What kind of audience members do you look for when you interact? You always seem to pick out the perfect audience member and it builds so much throughout the set.

The first thing I look for is the person who doesn’t seem to be enjoying it at all, then I make them get involved. Or, if I hear that one person hasn’t laughed the whole show, or “This person’s been kind of shitty or has heckled,” I try to attack the problems first.

Has that ever backfired on you?

When I do that I definitely encourage them to start laughing and enjoy themselves and realize they shouldn’t be so uptight or so down in the dumps. Sometimes they’re just shitty. Weirdly enough the thing I’m not looking to do is probably where I shine the most. I’m really good up against the wall.

I try not to get into that world – there’re a lot of comics where it goes, “Hey, what’s this? Is it your wife? What do you do for a living?” So they go in shitty and they’re like “Fuck you, I’ll beat the shit out of you! You wanna go outside, motherfucker?!” There’re comics where it gets to that point. I’ve seen a bunch of comics get involved in that. I think I’m pretty good at really winning that situation still, like really being aggressive in that situation but keeping it funny still. So that the rest of the crowd is still laughing even though that one person is getting more and more furious.

Is that something you’ve developed through standup, or is that something that’s always been a part of you?

No, it’s definitely developed. It’s always been a part of me, but as far as being able to apply it, like actually putting it into action, it’s been through comedy.

The first thing you develop is not being afraid of the audience. If the audience terrifies you and you’re afraid of silence and them not laughing, you’re not gonna be able to do it anyway since there are probably going to be awkward moments in there where you have to be able to plow through. It’s kind of like having faith in your own stats in a weird way.

I think I do better more times than I do badly, for sure, and in that regard, you do it so many times every night for so many years that you kind of get the idea that you know you’re at least pretty good at this. So I don’t think I’m the best, I don’t think I have of any kind of “elite status” or anything, but I think I can conduct myself pretty well onstage.

Just being as comfortable on stage as you would be chatting among friends.

I’m not afraid to go silent if the crowd doesn’t laugh at something I say, or if I say something so mean to the person, even though I’m trying to be funny. I’m not afraid that they’re gone for good. I always think I can get them back. It comes from the patience of staying in the pocket: not getting frazzled. At those moments I even turn it to the audience and be like, “Well, what happened here? Where did we lose? What was the problem?” And then hopefully someone speaks up and they’ll tell you and I can explain myself and make that funny and do whatever I can do. I would never apologize. And I’d say 9 times out of 10 I’m able to kind of pull that back in and get them.

Every comic has that skill in them and it’s why I run that set – an all crowd work show where all the comics go up and do crowd work. And they would get so frazzled before they’d go on, especially if they weren’t going on first. Like “Who do you talk to? What do you say now?” But we all have this skill, it’s just a matter of calling on it, as much as anything else. You were funny before you did standup comedy. You didn’t prepare to be funny with your friends. You didn’t write down a bunch of stuff in a book with your friends so they’d laugh when they’d come over – you just were. You were just organically funny. You were funny, you were the guy who had the smartass response. But you never overly concerned yourself with it, and that’s kind of the thing. If you get things to relax and breathe, you’ll find that zone. Like you just go into it and you’ll be funny off the cuff. The same way a lot of these guys when they do interviews or they’re on the radio in the morning are just funny. You don’t overthink it, but when you see that audience staring at you with some kind of expectation, when people don’t have their jokes to rely on, sometimes they panic.

All it is – I’m no better than any of these guys. I just have exercised that muscle so much that I’m not afraid of seeing where it goes. I might say something and the crowd might go, “What? What does that reference mean? Why would he say that?” I’m not afraid of that. I’ll talk them through that.

And you’ve developed the ability to be comfortable in any circumstance.

Starting out in that black circuit really does prepare you for adversity. [Laughs.]

Have you gotten to a point where you’re just comfortable on any stage?

I’m always comfortable. There are definitely times when I’m onstage and I am waiting for that light. When I’m doing spots in the city, they’re always 15 minutes, tops, so that goes by really quickly whether you’re doing good or bad. When I’m on the road though sometimes you have to do an hour for a crowd, but you’ve never really – again, I can’t even remember the last time I would say I bombed for an hour. I don’t even think that’s ever happened – just eating shit for a whole hour. I don’t think that’s ever happened to me before. But there’s definitely a difference between a crowd that’s on board and ready to have fun versus a crowd that every laugh is pulling teeth. And there’s those where I’m not uncomfortable – every joke I’m like “I can’t wait for this to be over.” When the light comes on for me to get offstage, I’m not gonna roll for an extra 15 because they’re a good crowd – like that I liked them so I’ll do an extra joke.

It’s not a matter of being comfortable, there are just definitely crowds where I’m like I don’t care about these people laughing. I’m not even certain the thing I’m gonna say here at the end is gonna get a big laugh. But I wouldn’t call that nerves as much as just getting out of a situation you’re not enjoying.

It feels like people are becoming a lot more sensitive to edgy material. You’re right in the middle of that: do you think audiences are becoming more receptive or less receptive?

I don’t know if it’s as general as the audiences are “more” or “less” receptive. There’s a thousand comics before me who paved the way. The fact that you can say the word “cunt” onstage and the whole audience doesn’t stand up and walk out… They’re desensitized in that way, and as far as being dirty, it’s really a combination of parts of the crowd.

Most people are followers, and I was having this conversation with somebody recently and I can’t remember who it was, but I will give credit that this is somebody else’s thought, but it was that… there are only a few alphas in every room. That sets the tone. So if they’re laughing at something, the crowd goes with them. If some of the people that are more vocal have an “oooh” attitude about it… I think I have the particular skill that has evolved, especially being as dirty of a comic as I am, something that is the x-factor of my goofy personality – I think I have a way of wording things that makes it palatable for people who maybe didn’t even think they were going to enjoy dirty comedy.

I don’t have any jokes that I write ever. When I first started, I didn’t have jokes that were for shock value. I didn’t think “I’ll say ‘pussy’ or ‘cunt’ here to get the crowd riled up.” Now very early in comedy a lot of comics do that because “oohs” and “aahs” are better than dead silence when you’re new to performing. It shows at least they’re listening. It proves to you that you have the control of the room even if it’s at the sacrifice of not laughing. I even have material now that are speeches designed to tell the audience to not waste their oohs and ahhs on me because of what a waste of time that is.

The crowd has to be somewhere between not thinking too much and not blindly reacting too much.

I don’t want the crowd to be shocked by me using the word “cunt.” I want you to not overthink that and just listen to the hilarious joke I wrote that has the word “cunt” in it. I want you to hear my funny thought. If you just go off on the word cunt, I think that’s sad. There’s a lot of comics, “dirty comics,” and I used to get lumped in with a lot of people and I don’t think they’re bad people or anything but I didn’t think we did the same thing at all, just because they’re “dirty.” There’s dirty comics who will have a punchline like “fuck her in the ass until she’s shitting blood all over her dad’s sheets,” and I’m like “Jesus Christ. That’s not funny to me.” It was these aggressive dirty words. Or it’s like, you’ve gotta paint a better picture than that if you wanna make somebody laugh. I’m not even saying the elements of those words can’t be involved, but – I don’t know. It’s intangible. If I had that thought I think I’d find a way that I could say that in someway that a lady in her early ‘60s would not hit me with a purse. Instead she’d just shake her head like “Oh, jeez.”

So the album is going to be called The Crowd Work Sessions, Volume 1: What’s Your F@!?#ng Deal?! Is that to say you’re already looking ahead to a series of crowd work albums?

We left the window open because if Comedy Central Records wants to, I could fart out one of these albums every couple of months. If we need to record, I can do 2 hours of crowd work the whole time and we’ll just see what happens.

It’s great. It’s a different performance every time you go up. You have a lot of production value on that end.

I try. I do that because there are comics in the city who work at the same club all the time, and I’ll walk out just seeing the waitstaff mouthing the words of someone’s joke while they’re rolling their eyes, because whenever they get the light they always start the same joke. “Here goes their closing bit – that bit they do to close every time for 15 years…” And the staff at the same time will be smiling in their face later, bright and cheery and friendly. My ego… Man, I just don’t want people shit talking me like that who I see all the time. So I think it came out of showing some kind of sympathy for the staff because they have to watch the same fucking comics every night, pretty much. They hear it all over and over again. I change the show everywhere I go. I go up there, it doesn’t really matter. I’ll go up and fuck around and have fun. At the very least, the audience will get into it. Then when the young comics get in that’s another sign. That’s all a good thing. That’s what kind of made me desire to do different sets like that all the time: to keep the staff entertained. Also, when you leave town or aren’t around and the staff at the comedy clubs in the city are with the owners or the bookers, the staff talks about you. Keeping your name in people’s minds is great.

Photo via La Mott Jackson Studios.

Phil Stamato lives and writes in New York, where he may also be seen standing up and telling jokes.

Turning the Show Around with Big Jay Oakerson