Big Jay Oakerson
Carolines New York, NY

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Big Jay Oakerson

For the first time ever, Big Jay Oakerson will headline a weekend at Carolines Comedy Club in New York City. Mark your calendars for March 30 – April 2nd.

So, to keep track, he just had his first hour special premiere on Comedy Central last year, season 2 of his WYFD crowdwork show is set to premiere on Seeso in April and he’s also the co-host of The Bonfire with Dan Soder on Sirius XM in addition to co-hosting both The SDR Show and Legion of Skanks podcasts.

Philadelphia born and raised Jay Oakerson, has risen the ranks of New York City comedy to become truly one of the best at the art of storytelling. Dubbed recently by the New York Times as a “Master of the Dirty Joke,” Jay has also mastered the art of Crowd Work.

Many may know Jay from his television appearances, most recently on Late Night with Jimmy Fallon. He is also known to many via the hit IFC show Z-Rock, where he received critical acclaim for his performance as “Neil,” the sexually ambiguous owner of a NYC rock club. His television credits also include Comedy Central’s Premium Blend and The Half Hour as well as Tough Crowd with Colin Quinn.” He’s appeared multiple times on BET’s Comic View and HBO’s P. Diddy’s Bad Boys of Comedy. His first hour stand-up special will be airing on Comedy Central in 2016.

Jay has been a stand out at comedy and music festivals around the world, including Just For Laughs in Montreal, Toronto and Australia. Additionally he has taken part in the New York Comedy Festival, South By Southwest, Moontower Festival in Austin, Tx., North By Northeast, Oddball Comedy Festvial, Mayhem Festival among others.

We’re running a contest for your chance to win a pair of tickets to see Big Jay in NYC during his headlining weekend. All you have to do is enter below for your chance to win!

Enter now for your chance to win tickets!


  • The contest ends at 12 noon (EDT) on Wednesday, March 29th
  • You must be 18 years of age or older to enter
  • One winner will be selected at random from all proper entries
  • Winner can select what show they’d like to attend that weekend
  • The winners will be notified via email and tickets will be available for pick up at the venue’s will-call.