Club Shay Shay - Gabriel Iglesias Part 1

Download the PrizePicks app today and use code SHANNON to get $50 in lineups after you play your first $5 lineup! 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.” See for privacy information.