Last Thursday, approximately 17 years after starting in comedy, Big Jay Oakerson sat down with Ron Bennington at The Stand Comedy Club in New York City, to talk about his career. Jay and Ron were taping a highly anticipated episode of Unmasked. Highly anticipated because Jay has been a regular guest on Bennington’s radio shows for years and has been a fan of Ron’s and Unmasked. The timing was perfect for Jay to guest on the critically acclaimed series. Comedy Central is about to premiere his first hour comedy special this Friday night- another major career milestone.
Oakerson’s fans packed into the club last Thursday to hear Jay talk about his start in comedy, his inspirations, his goals, and of course, to hear him share plenty of embarrassing stories about the early days. And he delivered. The stories are ridiculously funny- we’ll go so far as to say must hear, and we really don’t want to give too much away, so just trust us, this is an episode you won’t want to miss.
But just to give a few small teases, here are fragments of some of our favorite stories Oakerson shared throughout the hour:
Jay may be the first white comedian who struggled crossing over to working for white audiences. “I almost quit two years in. ‘Cause I did that black comedy circuit so much in the beginning and I saw the ceiling on it, I didn’t know how to kind of cross over at all.”
Big Jay has had an incredible run of scary funny comedians support him over the years. If you know anything about Jay, you know Dave Attell is one of those people, but there’s also been Ari Shaffir, Amy Schumer, Keith Robinson, Colin Quinn, just to name a few. Oakerson, by the way, does the best Keith Robinson impression we’ve ever heard.
Signs that you’ve “made it” in life, according to Jay: Bolo ties and the availability of fresh iced tea at all times.
Jay started with Kevin Hart in Philly, and also Kurt Metzger. In his early days, Kurt Metzger had the nickname “Bring ’em Back Kurt” and you probably won’t guess why.
Bob Kelly on Trial in Comedy Court. Jay told a hilarious story about doing some road gigs with Robert Kelly that ended with Kelly going “on trial” in front of the comics of the Comedy Cellar.
Jay dedicated his special to Patrice O’Neal. Jay was very close with Patrice O’Neal, and revealed that “there’s going to be a picture of him and a dedication at the end of my special.”
Starting at 12pm ET on Friday June 17th, SiriusXM’s Bennington Show will air two hours of some of the best of Jay’s appearances on the show, followed by the world premiere of the Unmasked episode. Big Jay Oakerson: Live at Webster Hall premieres on Friday night at midnight on Comedy Central.