In this special rewind episode of Club Shay Shay, revisit some of Shannon's favorite segments from the show so far. Today, the first-ever episode of Club Shay Shay, featuring Shannon's brother, Sterling.



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In this special rewind episode of Club Shay Shay, revisit some of Shannon's favorite segments from the show so far. Today, the first-ever episode of Club Shay Shay, featuring Shannon's brother, Sterling. Learn more about your ad choices. Visit <a href="https://megaphone.fm/adchoices">megaphone.fm/adchoices</a>

NFL legend Shannon Sharpe—3x Super Bowl champion and member of the Pro Football Hall of Fame—sits down with the biggest athletes, celebrities and influencers to discuss their accomplishments, challenges, and everything in-between.

NFL legend Shannon Sharpe—3x Super Bowl champion and member of the Pro Football Hall of Fame—sits down with the biggest athletes, celebrities and influencers to discuss their accomplishments, challenges, and everything in-between.

Club Shay Shay

In this special rewind episode of Club Shay Shay, revisit some of Shannon's favorite segments from the show so far.

REWIND: Sterling Sharpe makes a case for why he should be in the Hall of Fame

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/d76f9969-4563-4727-aea1-b06c00f7cd21/transcript

Download the PrizePicks app today and use code SHANNON to get $50 in lineups after you play your first $5 lineup! https://prizepicks.onelink.me/LME0/SHANNON 

Save the everyday with Amazon

Comedian and global touring star Gabriel Iglesias joins for a candid and hilarious conversation about fame, relationships, comedy, and the moments that shaped his career.

Gabriel opens up about the realities of dating and maintaining relationships while living a life on the road. As one of the most recognizable comedians in the world, he explains how constant fan interactions—sometimes happening every few steps in public—can create tension in relationships. Iglesias reflects on how fame complicates normal experiences like going out to dinner, and why partners have to understand the unique pressures that come with dating an entertainer.

The conversation turns to humor and attraction, with Gabriel joking that while abs may look good, a sense of humor is what truly wins people over. Known for making audiences laugh his entire life, he shares how comedy became his greatest asset—but also admits that personal struggles, including weight and avoiding difficult conversations in relationships, created challenges earlier in his life.

Iglesias then reflects on the moment he first discovered his comedic gift at just ten years old during a school talent show. Performing spot-on impressions of characters like Mickey Mouse, Ronald Reagan, and Pee-wee Herman, he stunned the audience and received a standing ovation—an experience that hooked him on performing long before he understood what stand-up comedy truly was.

Growing up, Gabriel found inspiration in the raw comedy he watched on Def Comedy Jam and BET's ComicView. Without many Latino comedians in the spotlight at the time, he gravitated toward stars like Martin Lawrence and D. L. Hughley, whose performances helped shape his understanding of stand-up. He even shares the surreal moment of finally meeting Martin Lawrence decades later and expressing how much his work meant to him.

Gabriel also talks about landing one of his early TV opportunities on ComicView and why young comedians should prioritize mastering the craft over chasing money or fame. For him, exposure and growth mattered far more than the small paycheck he earned at the time.

One of the most memorable stories comes from his first trip to New York to perform on Showtime at the Apollo at the legendary Apollo Theater in 1999, hosted by Steve Harvey. Gabriel recalls how brutally honest the Apollo audience was—and how he had to follow a fellow comedian who had just been booed off the stage. After advice from co-host Kiki Shepard about changing his outfit, Iglesias took the stage in a simple white T-shirt and delivered one of the best sets of his early career, earning a standing ovation.

He also shares the awkward aftermath of celebrating that huge moment while still sharing a hotel room with the comedian who bombed before him—and how even a second attempt at redemption at Carolines on Broadway didn’t go as planned.

Closes with highlighting Gabriel’s incredible career milestones—from selling out arenas worldwide to historic performances at venues like Madison Square Garden, Sydney Opera House, and Dodger Stadium—cementing the legacy of the comedian fans know and love as “Fluffy.”

Download the PrizePicks app today and use code SHANNON to get $50 in lineups after you play your first $5 lineup! <a href="https://prizepicks.onelink.me/LME0/SHANNON">https://prizepicks.onelink.me/LME0/SHANNON</a>&nbsp;
Save the everyday with Amazon
Comedian and global touring star Gabriel Iglesias joins for a candid and hilarious conversation about fame, relationships, comedy, and the moments that shaped his career.
Gabriel opens up about the realities of dating and maintaining relationships while living a life on the road. As one of the most recognizable comedians in the world, he explains how constant fan interactions&mdash;sometimes happening every few steps in public&mdash;can create tension in relationships. Iglesias reflects on how fame complicates normal experiences like going out to dinner, and why partners have to understand the unique pressures that come with dating an entertainer.
The conversation turns to humor and attraction, with Gabriel joking that while abs may look good, a sense of humor is what truly wins people over. Known for making audiences laugh his entire life, he shares how comedy became his greatest asset&mdash;but also admits that personal struggles, including weight and avoiding difficult conversations in relationships, created challenges earlier in his life.
Iglesias then reflects on the moment he first discovered his comedic gift at just ten years old during a school talent show. Performing spot-on impressions of characters like Mickey Mouse, Ronald Reagan, and Pee-wee Herman, he stunned the audience and received a standing ovation&mdash;an experience that hooked him on performing long before he understood what stand-up comedy truly was.
Growing up, Gabriel found inspiration in the raw comedy he watched on Def Comedy Jam and BET's ComicView. Without many Latino comedians in the spotlight at the time, he gravitated toward stars like Martin Lawrence and D. L. Hughley, whose performances helped shape his understanding of stand-up. He even shares the surreal moment of finally meeting Martin Lawrence decades later and expressing how much his work meant to him.
Gabriel also talks about landing one of his early TV opportunities on ComicView and why young comedians should prioritize mastering the craft over chasing money or fame. For him, exposure and growth mattered far more than the small paycheck he earned at the time.
One of the most memorable stories comes from his first trip to New York to perform on Showtime at the Apollo at the legendary Apollo Theater in 1999, hosted by Steve Harvey. Gabriel recalls how brutally honest the Apollo audience was&mdash;and how he had to follow a fellow comedian who had just been booed off the stage. After advice from co-host Kiki Shepard about changing his outfit, Iglesias took the stage in a simple white T-shirt and delivered one of the best sets of his early career, earning a standing ovation.
He also shares the awkward aftermath of celebrating that huge moment while still sharing a hotel room with the comedian who bombed before him&mdash;and how even a second attempt at redemption at Carolines on Broadway didn&rsquo;t go as planned.
Closes with highlighting Gabriel&rsquo;s incredible career milestones&mdash;from selling out arenas worldwide to historic performances at venues like Madison Square Garden, Sydney Opera House, and Dodger Stadium&mdash;cementing the legacy of the comedian fans know and love as &ldquo;Fluffy.&rdquo;

Club Shay Shay - Gabriel Iglesias Part 2

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/ef3514ff-db86-42a9-832a-b4090187ee26/transcript

Club Shay Shay - Gabriel Iglesias Part 1

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/0fea3581-9d28-4576-ad87-b4090187e3c3/transcript

Download the PrizePicks app today and use code SHANNON to get $50 in lineups after you play your first $5 lineup! https://prizepicks.onelink.me/LME0/SHANNON

Save the everyday with Amazon

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.

Download the PrizePicks app today and use code SHANNON to get $50 in lineups after you play your first $5 lineup! <a href="https://prizepicks.onelink.me/LME0/SHANNON">https://prizepicks.onelink.me/LME0/SHANNON</a>
Save the everyday with Amazon
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&rsquo;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&mdash;literally paying to watch him perform&mdash;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&mdash;including D.L. Hughley and Mike Epps&mdash;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 &rsquo;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&rsquo;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.

Club Shay Shay - Matt Rife Part 2

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/ff63140e-892e-4221-99b5-b404004fe976/transcript

REWIND: Sterling Sharpe makes a case for why he should be in the Hall of Fame

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