Shane Gillis hosting an awards show in 2025 was always going to be a "hold your breath" kind of situation. When ESPN announced the Mechanicsburg native would take the stage at the Dolby Theatre, everyone knew the vibe wouldn't be the usual safe, corporate banter. Honestly, it wasn't. The 2025 shane gillis espy highlights are basically a masterclass in how to make a room full of the world's most elite athletes feel incredibly awkward while simultaneously making the internet lose its mind.
It was polarizing. Some people called it the funniest thing to happen to sports media since Norm Macdonald’s legendary 1998 stint. Others found it cringey or straight-up offensive.
The "Deanna" Incident and the Caitlin Clark Jab
Things got weird early. Gillis started by trying to shout out WNBA legend Diana Taurasi. He called her "Deanna." The camera cut to Taurasi, and she looked like she wanted to be anywhere else. She wasn't smiling. She was just shaking her head while Gillis scrambled with a "My bad on that."
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But the real fire started when he pivoted to Caitlin Clark. Clark wasn't even in the building—she was nursing an injury before the All-Star break—but that didn't stop Shane. He joked that when she retires, she’ll end up working at a Waffle House so she can keep doing what she loves: "fist-fighting Black women."
The room went quiet. Like, pin-drop quiet.
On one hand, you've got the "it’s just a joke" crowd on X (formerly Twitter) laughing at the absurdity. On the other, you have folks pointing out that WNBA players have been dealing with a massive wave of online toxicity, making the joke land a bit too heavy for a celebratory night.
Why the Bill Belichick "Bookie" Joke Actually Worked
If there was one moment where the audience actually loosened up, it was the Bill Belichick stuff. At 73, the new North Carolina head coach is dating 24-year-old Jordon Hudson. That’s a lot of material for a guy like Gillis.
He leaned into the age gap hard. He joked that a "bookie" is just what Belichick reads to his girlfriend before bed. He listed off fake titles like The Very Horny Caterpillar and The Little Engine That Could But Needed a Pill First.
It was silly. It was biting. And for a second, the tension in the Dolby Theatre actually broke.
"He won six Super Bowls. He’s dating a hot 24-year-old. Maybe if you guys won six Super Bowls, you wouldn't be sitting next to a fat, ugly dog wife." — Shane Gillis, immediately realizing he maybe shouldn't have said that last part.
He literally admitted on stage that he should have cut that part of the joke. That's the Shane Gillis experience: pushing the line, crossing it, and then pointing at the line from the other side while looking slightly terrified.
Political Jabs and the Norm Macdonald Tribute
You can't give Shane Gillis a microphone and expect him not to talk about Donald Trump or Joe Rogan. He did a bit about Joe Rogan thinking NBA Commissioner Adam Silver is an alien. He also took a swing at Trump’s idea of staging a UFC fight on the White House lawn, quipping that the last time Trump staged a fight in D.C., "Mike Pence almost died."
But the most "Shane" moment of the shane gillis espy highlights was his tribute to Norm Macdonald. He basically did a cover of Norm's infamous O.J. Simpson joke.
Congratulating Colorado’s Travis Hunter on his Heisman win, Gillis told him it’s something they can never take away from him—unless he kills his wife and a waiter. It was a direct callback to 1998. It was a moment for the comedy nerds, even if the athletes in the front row looked like they were reconsidering their career choices.
The "Tush Push" Skit and Local Roots
Being a die-hard Philadelphia Eagles fan is a core part of Shane's identity. He didn't just stay on the stage; he leaned into his fandom with a pre-taped skit about the "tush push."
Working with comedian Druski, the skit explored the "origins" of the play. Gillis spent a good portion of it calling every NFL team that tried to ban the play "cowards." Later, he even chatted with Eagles head coach Nick Sirianni in the crowd. Sirianni actually seemed to enjoy it, which was a rare moment of genuine athlete-comedian synergy during the night.
A Quick Breakdown of the Room's Reaction:
- The Boos: Mostly came during the Caitlin Clark and Donald Trump jokes.
- The Laughs: Belichick’s "bedtime stories" and the Shai Gilgeous-Alexander "foul trouble" joke.
- The Silence: The Jeffrey Epstein "deleted joke" bit.
Was it a Bomb or a Success?
It depends on who you ask. If you're looking at the faces of the people in the Dolby Theatre, it looked like a struggle. Athletes are notoriously bad at being the butt of the joke. They spend their lives being praised and protected; getting roasted by a guy in a suit who looks like he just rolled out of a dive bar is a culture shock.
But if you look at the metrics, it was a massive win for ESPN. The clips of the shane gillis espy highlights generated more engagement than the actual awards.
What to Take Away From the Night
The 2025 ESPYs proved that the "roast" format of award shows is still alive, but it’s getting harder to pull off. Gillis didn't pander. He didn't play it safe. He stayed true to the style that made his Netflix show Tires and his stand-up specials huge hits.
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If you're a fan of comedy that makes you a little uncomfortable, this was a top-tier performance. If you prefer the polished, "we're all friends here" vibe of Jimmy Kimmel, you probably hated it.
Next Steps for Fans:
- Watch the Tush Push Skit: It's the most "accessible" part of his hosting gig and shows his genuine love for the game.
- Compare to 1998: Go back and watch Norm Macdonald’s ESPY monologue. You’ll see exactly where Shane was getting his inspiration.
- Check out MSSP: If you want to hear the "behind the scenes" of how he felt about the night, he'll almost certainly break it down on Matt and Shane’s Secret Podcast.
Ultimately, Shane Gillis did exactly what he was hired to do: he made people talk about the ESPYs. Whether you're laughing or cringing, you're definitely watching.