WIN!!! Who Wants Tickets to See Big Jay Oakerson Headlining Carolines?

Big Jay Oakerson is headlining Carolines all weekend- that’s Thursday, May 3, through Sunday, May 6.  

We’re so excited, that we are giving away some pairs of tickets to see Jay!  Do you want to win tickets? Just fill out the form below by Wednesday at 10 pm eastern time.

And just for fun, we’re re-running our “What Would Jay Say” game that we posted last year.

Showtimes are Thursday, May 3 at 7:30 pm, Friday, May 4 at 7:30 and 10 pm, Saturday, May 5 at 7:30 and 10 pm and Sunday, May 6 at 9:00.

Big Jay is not only the co-host of  SiriusXM’s The Bonfire and the Legion of Skanks and SDR Podcasts, he’s also hands down one of the funniest comedians performing in the country today.  He also hosts “What’s Your Fucking Deal” which just killed every night at Austin’s Moontower Comedy Festival. He’s a personal favorite and if you’ve never gotten to see him headline, then you need these tickets. If you’ve seen him before you don’t need us to convince you how great it would be to get a free pair.

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, and we agree with the New York Times that Jay is the “Master of the Dirty Joke.” You’ve seen him on Conan, and Fallon and of course his Comedy Central hour special stand-up special, “Live at Webster Hall.”  He’s at every major comedy festival-  Just For Laughs in Montreal, Toronto and Australia, SXSW, Moontower, Colossal Clusterfest, Skankfest, North by Northeast, Mayhem, Oddball Festival, and this year he recorded a new album during the New York Comedy Festival.

Enter here to win and we’ll see you at Carolines!

Sorry this contest has ended! Thanks for entering!

Click here to buy tickets and go to Carolines.com for more information.

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Here are the questions, click the box below each question to see the answer:

Q1: Who was the first comedian Big Jay ever met? Greer Barnes or Kevin Hart?

What did Big Jay say!?

Greer Barnes in 1999 at the Laff House in Philly. He was wearing overalls, time appropriate.


Q2: According to Jay, who is the greatest 80’s band, music group or solo artist? Hall and Oates or Toto?

What did Big Jay say!?

Toto: Simply for making the masterpiece that is “Africa”.


Q3: What was the movie that made Big Jay cry? Rocky or Armageddon?

What did Big Jay say!?

Armageddon: While on a date with a white girl who was certainly not into white guys.


Q4: How does Jay drink his coffee? Black like a real man or 3 pumps of chai, coconut milk, hold the coffee?

What did Big Jay say!?

I drink it 3 pumps of chai, coconut milk, hold the coffee.


Q5: What did little Jay want to be when he grew up? Male Porn Star or Cowboy?

What did Big Jay say!?

Male Porn Star: Turns out, didn’t have the dick or bod for it.


Q6: What’s Big Jay’s pick for the best candy bar?  Take Five or 100 Grand?

What did Big Jay say!?

Take 5: If you disagree, I don’t want you in my life.


Q7: What is Jay’s favorite animated TV show? Archer or American Dad?

What did Big Jay say!?

American Dad: Every character is perfect.


Q8: Did Big Jay ever fake an orgasm?  Yes or No?

What did Big Jay say!?

Yes: When I lost my virginity, just so it could end and I could tell people


Q9: What is Big Jay’s guilty pleasure TV show go-to? Bad Girls Club or RuPaul’s Drag Race?

What did Big Jay say!?

Bad Girls Club: Girls fighting and nudity. Two of my lifelong faves..



Bonus Question: What would you be doing if not stand up comedy?

What did Big Jay say!?

Camera guy on Bad Girls Club. 1000%


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