Big Jay Oakerson has room for everyone around his comedy bonfire

Via Artist

With new material at the ready, the NYC-based comedy vet is looking forward to celebrating in style in the Seaport

Whether it’s because of his birthday on Saturday, or his Bonfire battery mate Dan Soder’s HBO special premiere, or the fact that he doesn’t have to get on a plane to make the trip to Boston, Big Jay Oakerson has a lot to be excited about this weekend.

Always one to keep things loose, Oakerson is looking forward to mixing it up with the crowds at Laugh Boston, where he’ll be camped for four shows starting on Thursday (December 5). While his crowd work-heavy delivery has allowed him to keep every show fairly unique in their own right, an even bigger highlight for Oakerson as he makes his way to the Seaport is the chance to do something he’s been able to achieve over the course of his entire career, and do his thing for a vastly diverse crowd.

“I like that I have a very diverse audience for the most part, from social workers to guys with neck tattoos, because I think it just shows that, even with all of the stuff going in comedy whether it be what people see as racism or people saying it’s hate speech, I like being able to bring people together,” Oakerson tells Vanyaland. “Everybody in that room can’t be wrong if they’re all there laughing together. I mean, if it was just the guys with neck tattoos, then maybe you’d think I’m hammering home some specific kind of point, but that’s not what’s happening.”


In addition to his inclusive stand-up shows, Oakerson has been hard at work growing his podcasts, Legion of Skanks and The Bonfire, as well as his newest monthly live show, The Worst at The Stand in New York City, while he looks for a new home for his former Seeso network show, What’s Your Fucking Deal?!

There’s a lot on Oakerson’s plate for 2020, but it’s all good vibes going into the new year, as the stand-up vet is just happy for the opportunities he’s had, and the chance to work alongside his friends makes it all worth it.

“There’s a lot of fun stuff in the works right now,” says Oakerson. “It’s always great to be able to do this kind of stuff with friends, and have people recognize it.”


While he may be a Philly native, Oakerson has always felt a deep connection between how he and Bostonians see the world, even beyond his career-spanning friendships with Boston-bred legends like Patrice O’Neal and Robert Kelly. Appreciative of a hard-working, blue collar crowd who looks forward to laughing at cum jokes as much as his home city, Oakerson has always felt the love in Boston; but while he looks forward to indulging in a roast beef sandwich in the city, he admits that when it comes to regional culinary delicacies, it can really go either way.

“I’m looking forward to getting a roast beef sandwich up there, but I don’t trust ordering a cheesesteak up there, because when I say ‘cheesesteak,’ and they say ‘steak and cheese,’ I just walk out. Patrice [O’Neal] and I used to argue about it all the time,” says Oakerson. “But Patrice was a huge mentor to me, and Bobby Kelly has been a mentor and friend for so many years, and there’s just that vibe and attitude from Boston that I’m drawn to.”

BIG JAY OAKERSON :: Thursday, December 5 to Saturday, December 7 at Laugh Boston, 425 Summer St. in Boston, MA :: Thursday at 8 p.m., Friday at 7:30 p.m., Saturday at 8 p.m. and 10:15 p.m., $20 to $25 :: Laugh Boston event page