Skip to content
Brick Wall Comedy
Brick Wall Comedy
Promotional art for Live at Webster Hall
Cover image credit: Promotional image via Prime Video

Live at Webster Hall

Big Jay Oakerson

Comedy Central · 2016 · 68 min

A filthy hour of crowd work and stand-up from Webster Hall.

Watch on Comedy Central(opens in a new tab)

or watch it free on YouTube (opens in a new tab)

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.

The set list

4 bits

  1. Men with small penises

    Argues why men with small penises deserve love and provides advice to women on how to delicately navigate intimate situations with underendowed partners.

  2. My Friend Dave

    Examines the absurdities of male friendship and perceived sexual tension between Oakerson and his best friend Dave.

  3. Raising a daughter and taboo family dynamics

    Shares brutal truths about fatherhood, dealing with a teenage daughter, and childhood memories of growing up with stepparents.

  4. Navigating the friend zone

    Breaks down the unspoken rules and awkward realities of trying to escape the friend zone.

How it plays

Tone
Crass, blue, honest, irreverent, and unapologetic.
On stage
The self-proclaimed 'king of sit down comedy' who performs seated on a stool on a custom lower thrust to feel close and casual like a bar buddy, blending raw, self-deprecating vulgarity with disarming comfort and warmth.
Pace
Low-key, patient, and conversational rather than frenzied, drawing the audience inward with a relaxed tempo that gives him complete control of the room.
About
penis size and sexual dynamics, parenting a teenage daughter, growing up with stepparents, male friendship and sexual tension, the friend zone, cringe-worthy humor and taboo comedy

What the critics said

Praised as classic Oakerson that thrives on deft, fearless crowd work and unabashed blue humor, turning crass toilet humor and dick jokes into an engaging, relatable, and authentic hour.

In the room: Resilient, highly engaged, and intimate despite the venue size, embracing Oakerson's offensive premises and unscripted crowd exchanges.

Summed up from reviews, articles and listings. Sources: cc.com, bigjaycomedy.com, themoviedb.org, tv.apple.com, vulture.com, exclaim.ca, inquirer.com, en.wikipedia.org.

Backstory

Balancing life as a touring comedian and father raising a 13-year-old daughter, translating his reputation as an unfiltered, blue club comic and master of crowd work to a wider television audience.

Details

Released
Taped
Webster Hall, New York City
Runtime
68 min
Where
Comedy Central
Director
Jeff Tomsic
Topics
After
The Crowd Work Sessions: I Promised Myself I Wouldn't Ask (2018)

More from Big Jay Oakerson

If you liked this