Shane Gillis hosting the 2025 ESPYs was always going to be a gamble. ESPN knew it, the athletes in the Dolby Theatre probably sensed it, and the "Dawgs" listening to his podcast definitely expected it. When the Philadelphia comedian stepped onto that stage on July 16, 2025, he didn't exactly go for the safe, pun-heavy humor we usually get from award show hosts. Instead, he went straight for the third rail of modern sports discourse: the WNBA.
It wasn't just a quick jab. It was a ten-minute tightrope walk that left half the room laughing and the other half looking like they wanted to call their agents.
The WNBA Punchline That Went Viral
Basically, Gillis took aim at the massive surge in popularity surrounding women’s basketball, specifically the hype around Indiana Fever star Caitlin Clark. He joked that when Clark eventually retires, she’s "going to work at a Waffle House so she can continue doing what she loves most: fist fighting Black women."
The joke was a heavy-handed reference to the physical play and the "Welcome to the league" moments Clark has faced from veterans like Angel Reese and Chennedy Carter. Some people in the crowd groaned. You could actually hear the air leave the room in a few spots. But online? The clip racked up millions of views within hours.
It’s that classic Shane Gillis energy. He plays with the tension. He knows he’s the "bad boy" who got fired from SNL only to come back as a hero to a specific segment of the internet. By the way, he also joked about how he and Clark have a lot in common because they are "both whites from the Midwest who have nailed a bunch of 3s."
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Mispronouncing a Legend: The Diana Taurasi Moment
If the Caitlin Clark stuff was edgy, the Diana Taurasi moment was just plain awkward. Early in the monologue, Gillis tried to give a shoutout to the legendary Taurasi, who was set to receive the Icon Award later that night. The problem? He called her "Deanna."
The camera panned to Taurasi, and she was not having it. She sat there stone-faced, shaking her head. Gillis caught himself pretty fast, muttering, "My bad on that," but the damage was done. For critics, it felt like a lack of respect for one of the greatest athletes to ever pick up a ball. For fans of Gillis, it was just another "Shane being Shane" moment where he plays the part of the bumbling, slightly unpolished guy who doesn't really belong in a tuxedo.
Honestly, it's hard to tell if the mispronunciation was a genuine slip or a bit of "calculated incompetence" to keep the audience off balance.
Beyond the Court: Trump, Epstein, and Belichick
The Shane Gillis ESPYs WNBA segment might have been the most controversial, but he didn't stop there. He went after the whole room.
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- Bill Belichick: He roasted the former Patriots coach for his relationship with 24-year-old Jordon Hudson. He joked that a "bookie" is what Belichick reads to his girlfriend at night, including titles like The Very Horny Caterpillar and Goodnight Boobs.
- Donald Trump: He riffed on the former president wanting to stage a UFC fight on the White House lawn, quipping that the last time Trump staged a fight in D.C., Mike Pence "almost died."
- The Epstein "Deleted" Joke: He even joked that there was supposed to be a Jeffrey Epstein joke in his script, but it "got deleted." Then he doubled down, saying it probably never existed and we should all just move on.
It was a lot. At one point, Gillis even looked at the unsmiling crowd and said, "I see a lot of you don't like me and that's OK. I don't know why this happened."
Why This Monologue Still Matters
Hosting the ESPYs is notoriously one of the hardest jobs in comedy. Athletes are famously bad at laughing at themselves in public. They spend their lives being told they are heroes; they aren't exactly used to a guy from Mechanicsburg, Pennsylvania, telling them they look like they belong in a Waffle House brawl.
Norm Macdonald famously "bombed" the ESPYs in 1998 with jokes that are now considered legendary. Gillis clearly took a page from that book, even paying tribute to Norm toward the end of his set.
But the WNBA stuff feels different because the league is at a genuine turning point. For decades, the WNBA was the "punchline" of the sports world in a way that felt mean-spirited and dismissive. Now that it’s actually popular and drawing massive ratings, the humor has shifted. Gillis wasn't making fun of the league for being "boring"—he was making fun of the high-stakes, race-adjacent drama that has defined the 2024 and 2025 seasons.
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Actionable Takeaways from the ESPY Fallout
If you're following the career of Shane Gillis or the rise of the WNBA, here is what you actually need to know about the impact of this performance:
- Comedy is Decentralized: The "room" (the athletes in attendance) hated it, but the "internet" loved it. This is the new reality for award shows. Producers are now hiring hosts specifically to create "viral" moments for social media, even if it makes the live experience uncomfortable.
- The "Caitlin Clark Effect" is Real: The fact that a comedian can go on national TV and make a joke about Clark "fist fighting" people proves she is now a household name. You don't roast people nobody knows.
- The Line is Moving: Gillis is the first "canceled" comedian to fully integrate back into the mainstream while keeping his edge. This ESPY performance was a signal that Disney/ESPN are willing to tolerate high-risk humor to capture a younger, male-dominated demographic.
Whether you thought it was "cringe" or "hilarious," one thing is for sure: nobody was talking about the awards themselves the next morning. They were talking about the guy in the suit telling the best athletes in the world to lighten up.
Check out the full clips of the monologue if you want to see the reactions for yourself; the look on Diana Taurasi's face alone tells you everything you need to know about the vibe in that building.
Next Steps for the Reader
To understand the full context of the WNBA jokes, you should look into the 2024 rookie season of Caitlin Clark and the specific on-court incidents with the Chicago Sky. This provides the "lore" behind the Waffle House punchline. Additionally, watching Norm Macdonald's 1998 ESPY monologue gives a great perspective on how the "bombing" style of hosting is often a deliberate choice by top-tier comedians.