From the Archives: Unmasked with Big Jay Oakerson

Unmasked with Big

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As part of our new podcast sharing select archival episodes of ’s epic interview series Unmasked, this week we are sharing Unmasked with Big Jay Oakerson. The Unmasked series which began in 2008 with a brilliant hour with Patrice O’Neal has taped nearly 200 episodes since, documenting the careers of the most interesting comedy writers, directors, filmmakers, actors, screenwriters, satirists, political comedians, comedic musicians and of course, stand up comedians in the business. It is a veritable archive of the greatest comedy of our time. Past Unmasked guests have included , Bob Newhart, , Dan Aykroyd, Simon Pegg, , , Jim Jefferies, Gilbert Gottfried, Bobcat Goldthwait, Louis C.K., David Brenner, , Patrice O’Neal and over 150 more comedy greats.

In this episode, Ron Bennington sits down with Big Jay Oakerson in front of a packed house at The Stand comedy club in New York City. It’s one of our favorite hours of the series, and Oakerson is full of hysterical stories about his start in comedy in the black rooms in Philadelphia, almost giving up and the one gig that kept him from changing his mind.  He also goes through his early attempts to break into the New York comedy scene with a story about going on the road with Bobby Kelly that you won’t want to miss. Big Jay’s evolution from his early days to his first Comedy Central hour special Big Jay Oakerson: Live at Webster Hall is absolutely must listen. We chose this as our first Unmasked to share through this

We chose this as our first Unmasked to share through this podcast, because it’s the audio equivalent of a page turner. Big Jay has been appearing on Ron’s radio show Bennington and the Show before that for years, and if you’ve been a fan of hearing Oakerson on all his other shows- SDR, The Bonfire, Legion of Skanks- you’ll get to hear a different side of him when he sits down with Ronnie B.


For anyone who isn’t already a giant Big Jay fan- and we don’t know how you could be a fan of the site and not be, but for formality’s sake, the New York Times called him the Master of the Dirty Joke in 2014, and we recently called Big Jay comedy’s next big rock star. He’s had a huge year- taping and airing his first hour special, touring his “Whats Your Fucking Deal” show and taping it for a second season on Seeso, and he has a hit radio show, The Bonfire, with Dan Soder.  He is one of our favorite stand-up performers, a master at crowd work, a great storyteller, and the only person we know who can still get away with wearing fingerless gloves. If you haven’t heard it yet, please enjoy and share it with someone else who loves comedy. Recorded on June 9, 2016 at The Stand in NYC, this is Unmasked, from the Archives, with Big Jay Oakerson and Ron Bennington.

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Check out our other Podcasts, Gail Meets Girls, and Big Brother and the Holding Kompany, here.


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