Live at Webster Hall

Big Jay Oakerson introduces himself in his debut hour-long special with a massive heavy-metal rock intro, only to immediately sit on a stool and call himself “a fat guy who’s gonna sit down and tell dick stories.” Filmed at Webster Hall in New York City, the 2016 Comedy Central special relies heavily on his trademark loose, conversational style and interactive crowd work. Rather than sticking strictly to a rigid script, Oakerson spends a significant portion of the hour bouncing off the front row, steering conversations toward the highly inappropriate and the deeply graphic. When he does use written material, it matches his black-clad, fingerless-gloved aesthetic: he talks about the anxieties of raising a teenage daughter, his preference that she become a lesbian so he does not have to deal with teenage boys, and the sexual tension between himself and his podcast co-host Dave Smith. He also presents a defense of why men with small penises deserve love. Directed by Jeff Tomsic, the special arrived during a busy period for Oakerson. In 2016, he was solidifying his place in the New York podcasting and radio scene, having recently launched The Bonfire on SiriusXM with Dan Soder and his crowd-work show What’s Your F@%king Deal?! on Seeso. The Webster Hall crowd, filled with a mix of metalheads, DJs, and long-time fans, provides the perfect backdrop for Oakerson’s brand of unfiltered filth.