Shane Gillis Makes Wild “Diddy” Joke at the ESPY’s

Shane Gillis Makes Wild “Diddy” Joke at the ESPY’s Shane Gillis Makes Wild “Diddy” Joke at the ESPY’s
Jul 16, 2025; Los Angeles, CA, USA; Grace Brassel and Shane Gillis on the red carpet before the ESPYS at The Dolby Theatre. Mandatory Credit: Kirby Lee-Imagn Images

Shane Gillis turned the 2025 ESPYs into an unforgettable spectacle on Wednesday night, taking center stage with a monologue that left no stone unturned. Blending humor with audacity, Gillis pushed the envelope, touching on everything from celebrity antics to his own life, while taking a swipe at everyone under the spotlight.

In true comic fashion, Gillis ventured into controversial territory, such as joking about the Diddy trial and poking fun at notorious parties. Sports icons, celebrities, and even Gillis himself felt the heat as he walked the fine line between wit and provocation. At one point, he playfully mispronounced Diana Taurasi’s name and riffed on Caitlin Clark, suggesting absurd scenarios that nudged at the boundaries of satire.

Demonstrating his knack for stirring the pot, Gillis humorously highlighted the unfamiliarity many have with WNBA players. He introduced an unsuspecting woman as a basketball star, drawing cheers from the audience, only to reveal she was actually his friend’s wife—a classic bait-and-switch maneuver that struck a chord with the crowd.

No one was safe, including Bill Belichick and his 24-year-old cheerleader companion, Jordon Hudson. As if saving the best for last, Gillis singled out Druski, who found himself embroiled in controversy related to a lawsuit linked to one of Diddy’s parties.

Wrapping up the night with his trademark humor, Gillis claimed there would be no afterparties, joking that they had been “ruined” by past excesses and pointedly highlighted Druski’s presence. It was all in good spirits, setting the tone for an evening that balanced humor with moments of sincere acknowledgment.

Despite the comedic edge, the ceremony didn’t shy away from inspiring moments. Penn State’s volleyball coach, Katie Schumacher-Cawley, was celebrated with the Jimmy V Award for Perseverance amidst her battle with breast cancer. Additionally, Sloane Stephens and the Indianapolis Colts were commended for their humanitarian efforts, reminding attendees of the positive impact sports figures can have beyond the game.

In the end, Shane Gillis delivered a performance that will be remembered for both its boldness and its lighter notes, encapsulating the essence of the ESPYs—a blend of humor, heart, and respect for the world of sports.