I can’t pinpoint when exactly I first discovered Shane Gillis. All I know is that it was just before he was seemingly everywhere.
In the time since that Saturday afternoon I spent binging his YouTube standup special and Netflix’s Beautiful Dogs — as well as several Gilly and Keeves skits and clips from Matt and Shane’s Secret Podcast — the Pennsylvania native has seemingly done it all. He’s hosted Saturday Night Live (twice), gone on a world tour, had a hit Netflix show and starred alongside Post Malone in a Super Bowl ad. He was even cast in an upcoming John Madden biopic featuring Nicolas Cage and Christian Bale, which I have a sneaking suspicion will launch his movie career.
Dan Le Batard recently referred to Gillis as “the biggest thing going right now in comedy” and it would be tough to disagree. And yet, despite his critical acclaim and burgeoning A-list fame, I still found myself caught off-guard when ESPN announced that he will be hosting the 2025 ESPYS, which will take place in Los Angeles on Wednesday night.
While the Worldwide Leader has already proven that it isn’t averse to Gillis’ off-color brand of humor, there’s a big difference between letting him poke fun at Nick Saban on College GameDay and making him the main character of your annual awards show. The history of ESPYS hosts would tell you that the network is typically keen on playing it safe, often turning to actors, athletes and occasionally comedians better known for their celebrity status than actual standup material.
To find the closest comparison to Gillis getting the gig at this point in his career, you’d have to go all the way back to 1998, when a Saturday Night Live cast member named Norm Macdonald took the stage at Radio City Music Hall. To paraphrase 2014 ESPYS host Drake, nothing was the same.
Even 27 years later, Macdonald’s ESPYS monologue remains one of the most memorable moments in the awards show’s history. Over the course of eight-plus minutes, the Dirty Work star refused to adhere to the sanctity of sports, mocking everything from the Bill Clinton-Monica Lewinsky scandal, Anthony Mason’s legal issues, Hideki Irabu’s ethnicity, and, of course, O.J. Simpson.
“Hey, there’s Charles Woodson. What a season he had,” Macdonald said, calling attention to the then-Michigan star. “He became the first defensive player to win the Heisman Trophy. Congratulations, Charles. That is something that no one can ever take away from you. Unless you kill your wife and a waiter, in which case all bets are off.”
Fair or not, that’s the standard that Gillis is going to be expected to live up to. And while it’s hard to imagine even the most talented comedian delivering a similar monologue on ABC airwaves in 2025, I vehemently disagree with Le Batard’s assertion that he’ll be “respectful” to the athletes in the room, some of which he’s friends with.
In fact, I’d argue that Gillis’ connection to the sports world will only make him feel more comfortable mocking the absurdity of it all. What will that look like? If I knew, I’d be a comedian. But listening to the latest episode of Matt and Shane’s Secret Podcast, it seemed clear that he’s not just going to make a handful of “respectful” jokes in an effort to avoid conflict with the athletes in attendance.
“They’re kind of excited about it,” Gillis said of the network’s reaction to him hosting as he shot pre-show promos. “I was joking like, ‘I’m going to do something crazy’ and they’re like using it. I had to be like, ‘get rid of that. I look like a dumbass.'”
After co-host Matt McCusker opined that ESPN and ABC would probably welcome a controversial performance, Gillis didn’t disagree.
What could that mean for Wednesday night? We’ll find out soon enough. But I’m glad ESPN is taking the chance and as a fan of Gillis’ work, I’m glad he’s getting the opportunity.
Most years, the ESPYS come and go providing little more than something to watch during the deadest week on the sports calendar. This year’s, however, feels like it could truly be a moment in time, whether it’s yet another launching pad for Gillis’ career or a monologue so memorable than we’re still talking about it nearly three decades later.