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Big Jay Oakerson is a product of both Philadelphia and New York, two cities that shaped his voice, his comedy, and his approach to the business. A longtime fixture of the New York comedy scene, Jay came up learning first-hand from the comedians he looked up to, absorbing the lessons, stories, and hard-earned knowledge of his idols while carving out his own path.
Now a veteran comedian, podcaster, and storyteller, Jay reflects on what it means to grow up in comedy while also growing up as a person. Becoming a young dad added another layer to that journey, giving him a perspective that reaches far beyond the stage. His comedy is rooted in real life: family, friendship, growing older, and the strange process of becoming the person you once looked up to.
Nate Jackson is a stand-up comedian, actor, writer, and entrepreneur from Tacoma, Washington. He began performing locally before creating the Super Funny Comedy Show and eventually opening the Super Funny Comedy Club, establishing himself as both a performer and a force in the comedy community.
As his career grew, Jackson became known for his high energy crowd work, which helped him build a massive online following while landing appearances on Wild ’N Out, Curb Your Enthusiasm, and Young Rock. That digital momentum expanded his audience far beyond the comedy club, leading to his 2025 Netflix special, Nate Jackson: Super Funny.
Today, Jackson tours nationally and internationally, continuing to build on the crowd work style that helped take him from a local comedian to a nationally recognized headliner.
Rick Messina has spent decades behind the scenes of the comedy business as a producer, manager, and talent representative, helping guide the careers of some of comedy’s most talented performers, including Tim Allen.
In this episode, Rick takes us inside his career and the world of comedy management, from discovering and developing talent to navigating relationships, the business side of the industry, and the realities of working alongside comedians as they build their careers.
He shares stories from his years in the business, the lessons he learned working with different talent, and what really happens behind the scenes of a comedian’s career.
In this episode Industry Standard, Eddie takes us behind the scenes of the comedy business, from the complicated relationship between managers and clients to how he sees the industry as a whole. He opens up about his own Achilles heel, what he would change about his life, and the moments in his career that make him most proud.
We also get a behind the scenes look at Eddie’s creative process, including the story behind his track/alter boy bit, Barry’s perspective on Eddie, and a deeper dive into his connections throughout the comedy world.
Yakov Smirnoff came to America from the Soviet Union in 1977 with little money and limited English, determined to build a new life. He started out working as a bartender before finding his way into stand up comedy, where he turned the culture shock of being an immigrant into his greatest source of material.
His career took him from comedy clubs to The Tonight Show, Night Court, and his own sitcom "What a Country!" making him one of the most recognizable comedians of the 1980s.
Behind the catchphrase is a remarkable story of an immigrant who used comedy to understand America and ultimately found his place in it.
Questions on this week's episode of Ask Me Anything #22
Josh Adam Meyers is a comedian with the energy of a rock star and the instincts of a stand up.
His comedy is loud, unpredictable, personal, and built around a fearless stage presence. He’s spent years carving out his own lane in comedy, bringing together storytelling, absurdity, music, and an unapologetic point of view.
He’s also the creator of The Goddamn Comedy Jam, proving that for Josh, comedy has never really needed to stay in one box.
Zoe Friedman has spent decades helping shape the comedy industry from behind the scenes. From discovering and developing stand up talent to booking for The Late Show with David Letterman, leading talent development at Comedy Central, and working with Jimmy Kimmel Live! Her influence has reached every level of comedy.
Today, as the co-founder and CEO of Comedy Gives Back, she continues to advocate for comedians by providing resources, support, and a stronger foundation for the comedy community.
Questions answered in this episode of Ask Me Anything:
Adam Conover started out doing sketch comedy and stand-up before landing at CollegeHumor, where his sharp, curious style quickly stood out. That eventually led to Adam Ruins Everything, the show that put him on the map and helped carve out his unique voice, mixing comedy with a love of asking questions and challenging conventional wisdom.
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