Big Jay Oakerson & Ari Shaffir

Who is Big Jay Oakerson & Ari Shaffir?

Big Jay Oakerson is a stand-up comedian, on-air personality, and podcaster known for hosting The Legion of Skanks, SDR Show, and The Bonfire podcasts, with a new comedy special 'Dog Belly' premiering on YouTube. Ari Shaffir is a stand-up comic and podcast host of The Skeptic Tank and You Be Trippin', with his latest special 'Ari Shaffir: Jew' available on YouTube. Both are established voices in the comedy podcast space known for irreverent humor and unfiltered conversation.

Topics and Timestamps

• 01Big Jay and Ari discuss their comedy careers and podcast empires
• 02Discussion of their new comedy specials and YouTube releases
• 03The evolution of stand-up comedy and podcast culture
• 04Behind-the-scenes stories from years of doing comedy together
• 05The creative process and comedy writing for specials
• 06How comedians build audiences in the modern streaming era
• ▶Introduction and catching up with Big Jay and Ari0:00:00
• ▶Discussion of Big Jay's 'Dog Belly' comedy special premiere0:15:00
• ▶Ari talks about his 'Jew' special and comedy material0:35:00
• ▶The state of stand-up comedy and podcast culture1:05:00
• ▶Reflections on their comedy careers and podcast empires2:00:00

The Show

This episode brings together two heavyweight comedy podcasters for what's likely a hilarious and unfiltered conversation. Big Jay Oakerson and Ari Shaffir have been fixtures in the comedy podcast world for years, building dedicated audiences through their various shows. Big Jay's work on The Legion of Skanks, The Bonfire, and his SDR Show has made him a recognizable voice in podcasting, while Ari's Skeptic Tank and You Be Trippin' have carved out their own loyal followings.

The timing of this episode coincides with Big Jay's new comedy special 'Dog Belly' hitting YouTube on April 5th, which likely became a major talking point. When comedians sit down together, especially ones with this much experience and chemistry, the conversation tends to flow naturally from their professional lives to the broader state of comedy and content creation. These two have probably spent years in the comedy trenches together, so there's likely plenty of war stories and inside jokes.

Ari's latest special 'Ari Shaffir: Jew' represents his current project, and the conversation probably touched on how both comedians are navigating the shift toward direct-to-audience platforms like YouTube for their specials. This is a significant departure from the traditional Netflix model, and both of them seem to be embracing this new era.

What makes conversations between established comedy podcasters so valuable is the meta-commentary on the industry itself. They likely discussed the evolution of stand-up, how podcasting has changed the comedy landscape, and what it takes to maintain relevance and audience connection in an increasingly fragmented media environment. These conversations are goldmines for anyone interested in comedy, entertainment entrepreneurship, or how content creators build sustainable careers.

Given their styles, the conversation probably wasn't confined to shop talk about their own projects. Both comedians are known for going deep into various topics and not shying away from controversial or unconventional subjects. The episode likely covered comedy philosophy, audience dynamics, the economics of podcasting and specials, and probably veered into personal stories that reveal what drives these comedians.

Best Quotes

Mentioned in This Episode

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