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Comedian and actor Matt Rife joins Shannon Sharpe on Club Shay Shay for a wide-ranging conversation about his rise from a young club comic to one of the biggest stand-up stars in the world. Now one of the highest-earning comedians working today, Rife reflects on selling out arenas across the globe, joining Taylor Swift as one of the only live acts to break Ticketmaster’s website due to overwhelming ticket demand, becoming the youngest comedian to sell out two shows at Madison Square Garden and the youngest stand-up to sell out the Hollywood Bowl, and building a massive audience through viral social media moments.

Rife opens up about growing up in Ohio and the childhood influences that shaped him, including being raised by his mother and grandfather after losing his father at a young age. He shares how his grandfather supported his dream early on—literally paying to watch him perform—and how that encouragement helped push him toward the stage. The conversation also touches on his early love of sports and the competitive mindset he developed growing up.

Starting stand-up as a teenager, Rife discusses studying comedians like Dave Chappelle, while learning how to write jokes, survive bombing on stage, and develop his own comedic voice. He talks about early comparisons to Justin Bieber, the mentors who helped him early in his career—including D.L. Hughley and Mike Epps—and how performing in Atlanta helped sharpen his skills before moving to Los Angeles after passing a California proficiency exam.

Rife reflects on becoming the youngest cast member in the history of Wild ’N Out with Nick Cannon, competing alongside comedians like DC Young Fly, Karlous Miller, and Chico Bean, and what he learned about television, exposure, and building a brand. He also addresses some of the public conversations and online speculation about his appearance that surfaced as his fame grew.

The discussion also touches on how viral moments online helped expand his audience, including clips of his crowd work that spread widely across social media. He breaks down the business side of comedy, touring worldwide, releasing specials independently, and navigating the changing landscape of entertainment platforms.

The conversation closes with reflections on the realities of fame, stories from memorable moments on stage, and what he’s hoping to accomplish in the next chapter of his career. Rife also previews upcoming projects, including his film Rolling Loud with Owen Wilson and the Netflix limited series The Altruist with Julia Garner, along with new tour dates across the U.S. and Europe.