JRE 2296 · March 28, 2025

Big Jay Oakerson

comedypodcastentertainmentstand-up

Who is Big Jay Oakerson?

Big Jay Oakerson is a stand-up comedian, podcaster, and on-air personality. He co-hosts "The Legion of Skanks," "Story Warz," and "The Bonfire." The first installment of his new crowd work special, "Them," is now available on YouTube. The second part, "They," premieres April 20.

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Topics and Timestamps

01Big Jay discusses his comedy special 'Them' and 'They' focusing on crowd work and audience interaction
02Conversation about the comedy podcast circuit and shows like The Legion of Skanks, Story Warz, and The Bonfire
03Big Jay shares stories about stand-up comedy experiences and the craft of crowd work
04Discussion of comedy as a career path and the evolution of his comedy style
05Talk about podcasting and creating content for multiple platforms
06Big Jay's approach to engaging with live audiences and building comedy material from real interactions
▶Big Jay discusses his new crowd work specials 'Them' and 'They'0:05:00
▶Conversation about The Legion of Skanks and other podcasts0:15:00
▶Big Jay explains the art and challenge of crowd work comedy0:25:00
▶Discussion of comedy career evolution and the podcast circuit0:45:00
▶Big Jay shares insights on filming crowd work specials for video1:00:00

The Show

Joe sits down with Big Jay Oakerson, one of comedy's most prolific voices across multiple podcast and comedy platforms. Big Jay is a fixture in the stand-up world and has built a substantial following through his work on The Legion of Skanks, Story Warz, and The Bonfire, where his quick wit and ability to work a crowd have made him a fan favorite.

The conversation centers heavily on Big Jay's new comedy special series. He's released the first installment called 'Them' on YouTube and has the second part, 'They,' premiering on April 20. These specials showcase what Big Jay does best: crowd work. Unlike traditional stand-up comedy that relies on pre-written material, crowd work is the art of improvisation with audience members, turning their responses and quirks into comedy gold. Big Jay has honed this skill over years of performing and it's become a signature part of his stage presence.

Big Jay opens up about the grind of being a working comedian across multiple shows and platforms. Between podcasting and touring, the workload is substantial, but it's also what keeps the creative juices flowing. The podcast circuit has become integral to modern comedy, allowing comedians to build closer relationships with their audiences and develop material in real time.

The discussion touches on the unique challenge of translating crowd work to video format. Traditional comedy specials capture pre-written material, but crowd work is inherently live and unpredictable. Big Jay talks about how filming a crowd work special requires a different approach because you're essentially gambling on whether the audience will give you the interactions you need to make the special work. It's riskier than traditional stand-up, but when it clicks, it's pure comedy magic.

Throughout the conversation, you get a sense of Big Jay's passion for comedy and his commitment to the craft. He's not just phoning it in on multiple platforms. Instead, he's actively engaged with developing his comedy, whether that's through live performances, podcasts, or specials. The comedy world has changed dramatically, and Big Jay has adapted by diversifying his presence while maintaining the quality of his work.