Big Jay Oakerson is Ready to Be America’s Next Comedy Rock Star, and Why It’s Finally His Time

On Sunday February 21st, New York’s historic rock venue Webster Hall was teeming with fans waiting for the show to start. Their raucous enthusiasm hadn’t been dampened by waiting in line for over an hour in a light drizzle, because they were the lucky ones who had received tickets in a lottery that left hundreds of others glumly sitting at home. After the opening act finished, the headliner strode out on stage to the wail of heavy metal guitars through an unfurled curtain bearing his highly recognizable logo that had been shredded to let the red backlighting show through like the glow from a fire. When the applause died down, he began. But this wasn’t a singer about to belt out a headbanger, this was stand-up comedian Big Jay Oakerson who was filming his debut hour special for Comedy Central.

The choice of location, of backing band, of styling, were all deliberate because Jay is a rock star in the comedy world. He’s literally performed with bands like Korn, Sevendust and Candlebox but fits in that world figuratively as well, drawing in the same fans as these bands with his down and dirty attitude and unique style.

And those fans can’t believe there’s anyone who doesn’t already know who Big Jay Oakerson is. Given the meteoric rise of his media profile over the last year, they’re finally right. Jay is now a major player and fan favorite on almost every form of media. He’s the co-host (with Dan Soder) of Comedy Central Radio/Sirius XM’s The Bonfire, star of the Comedy Central Digital series Lucky Loser, his live comedy series What’s Your F$%ing Deal? is a central part of the launch of NBC’s digital Seeso platform and his podcast Legion of Skanks grows in popularity week on week.

While Big Jay has only recently drawn national attention, he’s been at the comedy grind for 17 years, first in Philadelphia, then in New York and now all across the country at comedy clubs, festivals and even rock shows, gathering ever larger pockets of ardent fans. Just consider three special live events over the past few months. Beginning last summer with The Roast of Big Jay Oakerson which sold out The Creek and The Cave in under 10 minutes. The relatively small Long Island City comedy venue was overflowing with fans, comedians and folks from around the comedy industry and had to be simulcast in a separate room onsite to accommodate. His WYFD tapings at The Bitter End in November packed out that rock bar for eight tapings in four days, despite tickets being released only a few days ahead of time. And of course, there was the special taping, which drew hordes of fans, many of whom had come in from Philly or flown cross-country to be there.

It isn’t hard to understand how Jay has amassed such a loyal following…or why those same traits kept the industry from jumping on him earlier. First off, he’s a memorable character. You’d recall the big guy with the chain wallet, fingerless gloves and (until recently) long ponytail if you ran into him at a bar, never mind if he was onstage asking you if you’ve ever hooked up with the guy you came to the comedy show with as “Just Friends.” Second, he’s just plain talented. He is a master of storytelling and crowdwork, giving every audience a completely unique experience that often masks the fact that he is also a great joke writer. Third, you can kind of tell he’s actually just a giant kitten. Jay can get away with his outrageous interactions onstage because he is just so damn likeable. He’s not your creepy uncle at Thanksgiving, he’s the other uncle who told you your first dirty joke, then winked and gave you a quarter when your mother scolded him for it. Finally, he is uncompromising and unrepentant. Jay is an open book about his (mostly) formerly scumbag ways and often very un-PC opinions, which is exactly what makes him both difficult to package up in a nice little marketable box and practically a folk hero to his fans.

Jay’s “This is who I am, take it or leave it” attitude permeates Legion of Skanks, a twice-weekly podcast where Jay, Dave Smith and Luis J Gomez sit down with guests from comedy, TV, music, porn, wrestling and everything else that a teenaged boy from Philly might love. It’s mostly just a shit-shooting session, but often veers into dicey territory like a discussion on looking up girl’s skirts on the subway steps or which people with Down’s Syndrome they’d like to have sex with. In many ways, LoS has played a major role in the now steeper slope of Jay’s rise to prominence, with people tuning in around the country and then turning out to see Jay when he comes to town. His fanbase multiplied exponentially from his many beloved appearances on SiriusXM’s Ron and Fez show and later on its successor show, Bennington– a show he has been a fan of forever and helped shape his radio personality. And his appearances on Ari Shaffir’s Skeptic Tank – has given Jay another gigantic boost. Jay has made multiple appearances on ASST, and Ari is a favorite repeat visitor to LoS. Skeptic Tank helped propel Ari into the enviable position of maintaining an enormous amount of creative control over both his Comedy Central series, This is Not Happening. This creative control extended to much of the casting for Shaffir’s TiNH, where Ari accommodated a few network plants, but mostly insisted on using comedians who had done the live show and done it well, regardless of whether they had flashy credits or a CC series to cross promote. One of those comedians was Big Jay, who featured on both the digital series and the first season of the network broadcast. Watch some of the clips here, here and here.

Jay is no stranger to Comedy Central, who put out his albums An American Storyteller and What’s Your F@!?#NG Deal and featured him on showcases like Premium Blend and Comedy Underground with Dave Attell. But the bigger get of an hour-long special had gone through a series of near misses, never quite materializing. Until now. Jay credits Ari’s support on all fronts as a big factor in Comedy Central finally committing to putting a guy whose off-the-cuff act is certainly not PG-13 onto broadcast television. And that’s not the only new platform that has introduced Jay to a wider crowd. He and Dan Soder have become SiriusXM favorites with their show The Bonfire. Even Legion of Skanks recently received a broader reach, as it came under the umbrella of the Anthony Cumia Network.

All this has given whole new swaths of America the chance to fall in love with Jay, but it will likely bring him some new haters as well. Jay’s appeal is more immediately obvious to the kind of young men who feel marginalized by PC culture and revel in a space where men are unabashedly throwing around words like “cunt” and telling stories of banging groupies in comedy club bathrooms with a “boys will be boys” attitude. And while this goes over great with the reddit crowd, it doesn’t always sit well with folks who would rather be reading Jezebel. In fact, there’s been a long-standing beef between the Legion of Skanks crew and the women behind the Guys We Fucked podcast, who claim the Skanks’ laissez faire attitude and actions toward women are part of the problem, like catcalling or casting 25-year-old women as dumpy mothers.

That’s certainly one way of looking at it, but as with everything in life, the whole of it is a lot more complicated and nuanced. Jay has no shortage of female fans, including his adolescent daughter. Sort of. Like most 12-year-olds, she thinks her father is kind of lame. She even provided her godfather Kurt Metzger with a series of embarrassing stories for the Roast, with the sighs and eye rolls of her tween angst almost audible. Jay’s daughter, and simply the years of mellowing that have gone by since her birth, have given Jay a more complicated and rather protective view of women. Jay often worries about what she’ll be experiencing, knowing firsthand what horny young dudes are like. He extends that fatherly concern to other women in his life, often acting more like a father with a shotgun than a friend with a fauxhawk when it comes to their romantic lives. Of course, five minutes later, he’ll be egging on his male friends in their potential conquest of the day. He also has nothing but praise and respect for the women “running the show” in his life-like producer Rebecca Trent, producer/girlfriend Christine Evans and even his ex-wife. That contradictory mix of chauvinism, old-school gallantry and modern support for women is obviously not going to fly with folks who think even Amy Schumer and Tiny Fey aren’t “feminist enough.” But it is plenty of opening for your average comedy fan with two X chromosomes to find something to love.

Jay’s comedy also flirts with race and sexuality in ways that would get your average social justice warrior blogger’s hackle up. But he’s certainly not “punching down” (to use a ridiculous term), Jay approaches these topics with the same genuine curiosity and open mind he brings to a live crowd, poking and pushing from his own point of view, but willing to ride the ride in whatever unexpected direction it takes him, often learning something along the way.

From the Black Rooms of Philly to New York City Headliner

Jay started his comedy career in the urban rooms of Philadephia alongside Kevin Hart, Keith Robinson and Kurt Metzger. If you watch old clips of Jay’s early days, you’d never imagine that ‘wigger’ would turn out to be the co-host of a podcast called The Sex, Drugs, and Rock n Roll Show. Though Jay has shed the Fubu gear, he’s held on to much of who he was comedically at that time. As a white comic working black rooms, he had to quickly grab the audience’s attention and hold it through all kinds of disruptions from standard heckling to having chicken wings thrown at him. That ability to roll with the punches, react spontaneously and win over a hostile crowd are the bedrock of his act that is now more likely to come up against snooty sorority girls with their arms crossed than a united chorus of “nah nah nah nah, hey hey hey, goodbye.”

After moving to New York, Jay did the typical hustling for spots and working on new material until many of the guys from The Comedy Cellar began taking him on the road to feature for them. Jay began touring with Dave Attell fairly regularly, who he credits as both the ultimate comedy mentor and the kind of incredible joke writer Jay strives to match. It was during this period that the Big Jay Oakerson who became a cult hero emerged – his hair, his style of dress, his Attell-like fearlessness and his Patrice O’Neal-like habit of sitting on a stool and taking it at a slow pace.

While all this was going on, Jay’s old pal Kevin Hart was shooting to stardom, becoming arguably the most famous comedian in America and certainly one of the most successful. And comedy on television was changing. Shows like Insomniac with Dave Attell and Tough Crowd gave way to kinder, gentler “alternative” fare like Important Things with Demitri Martin and The Comedians of Comedy. Kids weren’t quoting Dave Attell and Colin Quinn to each other on the playground, they were rabidly gobbling up Patton Oswalt’s blog posts. For a while there, it seemed like Jay may get stuck a perpetual road dog “comedian’s comedian.”

Even at the height of the alternative comedy frenzy, New York City based website Cringe Humor was bucking the trend, promoting edgier, old school club-style comedy from guys like Nick DiPaolo, Quinn, Attell and, of course, Jay. As they expanded first to producing live shows at other venues, then to owning their own venue (NYC’s hot young thing The Stand) and a management company, Jay has been a key artist every step of the way. And now that the industry assesses commercial value based on numbers of Twitter followers or YouTube subscribers, the previously untapped legions of fans clamoring for “rock n roll comedy” is no longer being ignored. Comedy fans are also demanding a more realistic experience, one that captures the feeling of being live in a club rather than watching someone tell jokes in a strange theater-sized bubble. You can see this shift in Comedy Underground with Dave Attell, Ari Shaffir’s Paid Regular, Kurt Metzger’s White Precious, and even Jerrod Carmichael’s HBO special Love at The Store. Jay’s new Seeso series, What’s Your F$%ing Deal?! takes this trend to the next level.

Originally produced live at The Village Underground, it played to Jay’s strengths with crowdwork and the organic banter he had developed over years with The Comedy Cellar’s go-to emcee, Ardie Fuqua. Ardie would often stay in the room for Jay’s sets, teeing him up with facts he learned about various interesting audience members at the top of the show or calling shenanigans on audience members who answer Jay’s probing questions with timid bullshit. The Village Underground shows were this same experience writ large, with every act on the show asked to forgo their usual set to interact with the crowd and Ardie roaming the venue with a microphone to get even the people seated in the back booths involved. Producers Christine Evans and Rebecca Trent had always had an eye toward turning the live show into a television/digital series, but suffered a huge setback just as networks began expressing interest in it. Last June, Ardie was critically injured in the bus crash that killed Jimmy Mack (James McNair) and injured Harris Stanton and Tracy Morgan. But luckily Hollywood is slooooooow and in the kind of serendipity you only see in bad romcoms, What’s Your F#$ing Deal? got the green light from NBC the same week that Jay received a call from Ardie with the good news that he was medically cleared and felt up to re-emerging back into the world. An emotional Jay responded, “That’s great news, buddy… and I’ve got a job for you!” Despite Ardie’s 16 months away from the stage and serious head injuries that could have ended the career of someone whose bread and butter is thinking on their feet, the spark between the two was still there during filming as the pair guided heavyweights and young guns from both coasts through the potentially treacherous waters of relying on the crowd for a set.

Coinciding with this boost in recognition, Jay’s look has gone through another evolution. He’s lost enough weight that people jokingly call him Medium Jay Oakerson and he’s shorn the trademark ponytail in favor of a cut that’s somewhere between boy band and fauxhawk. It was a potentially risky move, after all, it’s one thing to root for the guy telling you graphic stories about spying on his friends’ hookups when he looks like a roadie who might still live in his parents’ basement. It’s a very different thing when that guy is good-looking and approachable. During the first set he did at The Stand with his new ‘do, there was an air of breath being held in the back of the room. How is this going to go? Fortunately Jay is still Jay, and his sincere degenerate warmth and charm shine through no matter what the external presentation is. He’s still the kind of guy whose friends don’t envy his success, they just pump their fists and say, “It’s about time!”

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