Shane Gillis ruffled plenty of feathers at the 2025 ESPYs on Wednesday night.

The comedian had the lion’s share of the spotlight and delivered an unforgettable monologue that was as funny as it was edgy. He even threw the Diddy trial into the mix, making a wild joke about his now-infamous parties at the end.

No one was safe from Shane’s roasting, as he went after sports icons and celebrities. And, of course, he had some jokes about himself.

There were several points where it felt like he may have been pulled off the stage, as he tap-danced on the line between satire and controversy, purposely mispronouncing Diana Taurasi’s name and joking about Caitlin Clark fist-fighting Black women.
Druski and Shane Gillis (Photo via ESPN)
He would also suggest that people don’t know WNBA players by introducing a random woman as a women’s basketball star and getting everyone to cheer for her before claiming she was his friend’s wife.

Shane Gillis Put Druski On The Spot

Shane Gillis (Photo via Twitter)

Gillis would also dump on Bill Belichick’s relationship with 24-year-old cheerleader Jordon Hudson, while Druski, who found himself named in a lawsuit alleging sexual abuse at a Diddy party, was singled out while on stage at the end.

With the event coming to a close, he said that there would be no afterparties, given that they have been “ruined” by the disgraced rapper.

“After parties have been ruined. You guys have pigged out at all the after parties. Now we’re not allowed to have them anymore,” he joked, pointing to Druski shortly after.

While it was mostly fun and games, there were many inspiring moments. Penn State volleyball coach Katie Schumacher-Cawley was honored with the Jimmy V Award for Perseverance while fighting breast cancer. Sloane Stephens and the Indianapolis Colts were also recognized for contributions to humanitarian causes.

Sure, Gillis put on a daring performance, but such events provide opportunities to get as raw as possible while avoiding serious backlash. He took full advantage.