The 2025 ESPY Awards will likely be remembered for Shane Gillis’ monologue, even if the comedy was largely forgettable.

Gillis, a standup comedian and the co-creator and star of Netflix’s Tires, is probably best known for lasting like four hours at Saturday Night Live — Lorne Michaels felt compelled to fire Gillis after some non-PC clips of a 2018 episode of Matt and Shane’s Secret Podcast were resurfaced — though he has gone on to host the show, twice.

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By now, you’ve probably read both praise and criticism on Gillis’ monologue — he’s that kind of comic. Gillis is wildly popular among his base, and controversial among non-fans. This was always gonna go some sort of way, and ESPN executives knew that when they gave Gillis the gig. Gillis has appeared on the network’s College GameDay show, where he (internet-)famously got into it with Nick Saban, an all-time great college football coach and an analyst on the popular ESPN program. Saban might not have an all-time great sense of humor.

There were some positives from Gillis’ ESPYs monologue. First of all, he dressed better than I’d expect, so there’s that; Gillis’ respect for the audience largely stopped there.

Though Gillis had some tough (even by modern awards-show standards) punchlines for some of the guests in attendance — and others who were not — he started off light and agreeable.

“[Oklahoma City Thunder star Shai Gilgeous-Alexander] is here, give it up for SGA. Hell yeah, bro,” Gillis said. “And now, everyone sitting around him is in foul trouble.”

It’s a good opener — a nice B+ joke that eases the audience into things (and comments on how the NBA overprotects its star players). It says Gillis is here to poke fun, not poke the bear. That was short-lived.

“Megan Rapinoe isn’t here,” Gillis said next. “Nice.”

That was the joke — and it was where things started to go sideways for the monologue. For Gillis fans, a punchline of “Nice.” and a smirk is kind of a staple of his persona — it’s almost a catchphrase. The joke is polarizing, sure, but so is Rapinoe to Gillis’ base (and vice-versa). Rapinoe, the U.S. soccer great, in 2016 kneeled during the national anthem in support of Colin Kaepernick. She’s ripped the NCAA in front of Congress and has called out U.S. Soccer in a discrimination suit.

The joke got some laughs — it was still early on and the benefit-of-the-doubt time. Gillis saved the moment somewhat.

“No? We’re gonna pretend she’s a good time?” he said. “Alright.”

Being unbothered by the negative reception of a joke or opinion is another Shane Gillis hallmark. He rolls with the punches as well as he throws punches.

Gillis is an anomaly. He presents as a right-wing good ol’ boy, but he’s not ignorant; Gillis does not fit neatly into the box that people project on him, and that can be confusing for crowds and critics. Like, what do you do when Shane Gillis makes Trump jokes? Let’s find out.

“Donald Trump wants to stage a UFC fight on the White House lawn,” Gillis said to a crowd that included some UFC greats. ”The last time he staged a fight in D.C., Mike Pence almost died.”

It took some time, but the joke — a reference to the January 6, 2021, attack on the U.S. Capitol — worked. It even got an applause break. It was as if the crowd collectively thought, “Oh, wait — is he on our side (politically)?” It’s another regular occurrence at a Shane Gillis show, where preconceived notions (one way or the other) don’t work out.

“There was supposed to be an Epstein joke here,” Gillis continued to roll at the ESPYs, gesturing to the teleprompter, “but I guess it got deleted.”

“It probably deleted itself, right? Probably never existed, actually,” he quipped. “Let’s move on as a country and ignore that.”

Gillis does not let you pin him down. It’s the political comedy you didn’t expect to get out of a big guy who looks like that and pals around with Joe Rogan.

We’re doing well here, both in terms of topical comedy and audience reception.

But just as quickly as Gillis got his good-guy status back among the Dolby Theatre-goers, he called out Karl-Anthony Towns in a reference to viral memes that depict the New York Knicks star as an effeminate defender of the basketball.

“The New York Knicks had a great season.”

Applause.

“Karl-Anthony Towns is here. Hey guuurl!”

Perhaps surprisingly, that one actually went over alright, which is really unfortunate for K.A.T. The (mostly) positive reaction to what was effectively a gay joke seems to indicate that a crowd full of Towns’ fellow professional athletes lost the “proper” public response to such material to a subconscious sense of agreement with its concept. That cannot feel good, regardless of whether you think the joke sucks or not.

The next joke was a Juneteenth joke, so you can probably guess how that played in the room.

“Maxx Crosby is here. I hope you had a good Juneteenth, brother.”

Crosby is not Black, but there is a narrative out there about him having a “pass” to use the N-word (with an “a” at the end, not “er”) in social settings. There is also a common assumption that Crosby caught himself in mid-use of the word in a 2023 call to action for Las Vegas Raiders fans. So the joke is intended to be on Crosby more so than a mockery of the holiday itself. But using the relatively new national holiday, which celebrates the ending of American slavery, as a peg for the punchline didn’t seem to go over with the ESPYs crowd — it’s possible the reference went over their heads.

Next, Gillis straight-up got booed — not by everyone, of course, though at least one guy was loud enough to hear on TV — but the negative response wasn’t really fair to the point of the joke.

“Joe Rogan actually wanted me to be here to host this awards show so that I could capture (NBA commissioner) Adam Silver, because Joe thinks he’s an alien,” Gillis said. “And Donald Trump wanted me to be here to capture Juan Soto, for the same reason.”

Saying Silver looks like an alien would be a cheap joke, but it’s not the joke here — it’s the setup. The joke is on President Trump and ICE — it is identifying the ridiculousness of the mass-deportation witch hunt. The groans and boos were a misunderstanding of the intention; they came from people who (likely) heard “alien” in the same sentence as the name of a popular baseball player from the Dominican Republic and instinctually found it to be an off-color joke told by a racist.

But that’s not going deep enough. Gillis is calling out what he (and 80 percent of the in-person crowd, probably) sees to be a racist initiative by the federal government. Soto is an alien by the definition of the word; many pro baseball players and a growing number of basketball players here are. Soto came to the U.S. in July 2015 when he was 16 years old — and only because he was drafted by the Washington Nationals, ironically. And also, the NBA commissioner, Silver, does look like a space alien.

Here, I should point out how difficult it is to have a consistently strong awards show monologue — now double that for the ESPYs. There, you can pretty much only make jokes about sports, and you’re telling them to some of the worst sports on the planet. These aren’t trained actors in the audience, many of whom make a living in the comedy space themselves. The ESPY Awards stage oversees a sea of some of the most disciplined, God-gifted, physical specimens on the planet — in other words, the people that bullied the rest of us into developing a sense of humor. When you look like DK Metcalf, no one makes fun of you.

The general reception to the monologue as a whole was mixed in the room, multiple ESPYs attendees told The Hollywood Reporter; some jokes were called “hilarious,” while others “missed the mark.” One production source told THR that the monologue played better in person than on the screen. That can often be the case, depending on the director’s camera choices and the venue’s audience-microphone placement.

Gillis bailed himself out with his next joke; he picked the perfect target for the perfect spot in his set.

“Aaron Rodgers did not take the (COVID-19) vaccine because he thought it would be bad for him,” Gillis said. “And then he joined the New York Jets.”

It’s funny because it’s true: There are very few things worse for you than playing for that organization. Rodgers is an easy target, but it’s not a cheap shot. Good joke.

The joke actually had a similar (low-key) political slant as the Soto joke — this one was just easier for the audience to digest. And it got Gillis on a roll.

“It’s a big year for the WNBA. I love Caitlin Clark,” Gillis said. “Caitlin Clark and I have a lot in common: we’re both whites from the Midwest who have nailed a bunch of threes.”

To borrow a phrase from Gillis here: Hell, yeah. The joke works because 1) it’s clever, and 2) Gillis made himself the butt of the joke. It gifted Gillis some grace for the next one, which was still a pretty good joke, but one that a decent portion of the live crowd withheld from laughing at. Their reasons are their reasons.

“When Caitlin Clark retires from the WNBA, she’s going to work at a Waffle House,” Gillis said, “so she can continue doing what she loves most: fist-fighting Black women.”

The joke here is about how many physical altercations Clark — a white woman — has gotten into in the WNBA, a predominantly Black league. Clark is the league’s biggest star and appears to be the target of regular physical antagonization on the court. The Waffle House clientele and behavior piece is, of course, a stereotype. But together, this is funny. We can laugh about these things together, right?

Well, maybe not the executives backstage. ESPN has been a staunch supporter of the WNBA (and the NBA), and recently signed another long-term TV deal to continue broadcasting games. They could not have loved the multiple shots taken at one league in such a relatively short period of time.

Unfortunately, after that, Gillis definitely did not land the plane.

At one point, he went on a run about legendary New England Patriots coach Bill Belichick and his much younger girlfriend, Jordon Hudson. They’ve certainly made themselves fair game. But one joke was a particularly ill-advised shot about the WAGS (wives and girlfriends of sportsmen) in the crowd. The problem was, it was barely a joke.

“[Bill Belichick] has 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.”

Woof.

Why go there? Well, the idea is that Belichick is one of sports’ greatest winners of all time, and his dating life is now reaping the rewards — athletes in attendance, in 50 years, this could be you. But the real reason Shane told the joke is to revel in the discomfort it created. He knew it wasn’t good, but the opportunity to create chaos was alluring.

“They let me do it. This is Disney. They allowed that,” Gillis said. “We should have taken that out. I had doubts going into that — that didn’t work all week.”

Gillis is an envelope-pusher as much as he is a button-pusher.

But it wasn’t worth it, because mean-spirited comedy doesn’t work when it’s not funny. Fellow standup comedian Anthony Jeselnik has made a lucrative career out of making jokes about the most heinous topics you can imagine; it’s literally his writing strategy. But he only tells the joke if he comes up with a genius punchline, which Jeselnik almost always does. That wasn’t this.

In case of emergency, break glass and make fun of Trump.

Gillis attempted to recover the moment by spending more than two precious minutes of a 10-minute set telling an aimless story about meeting Trump at college football’s National Championship Game. He pulled out a (quite good) impression of the POTUS, but to borrow a phrase overused in journalism, there wasn’t much there there.

Shane mostly offset the jokes for those on the left with jokes for those on the right. Another WNBA joke — a cheap one about WNBA players looking like men combined with the champion New York Liberty not attending the White House (to the best of the public’s knowledge, they weren’t invited) — didn’t work. It also just made things officially weird. There were so many WNBA jokes in the monologue. It’s a bit of tipping your hand, and it’s not a good look.

Gillis had one last chance to win the day. And to some degree, he did, endearing himself to the audience with a sweet, thoughtful, meta tribute.

“There’s one thing I wanna say before I get out of here,” Gillis wound down. “You guys aren’t gonna like it.”

Oh, OK then. Please go on?

“But it was a Norm Macdonald joke that I loved when he hosted the ESPYs and I’m gonna do it now,” Gillis continued.

“Travis Hunter won the Heisman Trophy this year. He’s the first defensive player since Charles Woodson to win the Heisman. Congratulations, Travis Hunter. Winning the Heisman — that’s something they can never take away from you. Unless you kill your wife and a waiter.”

Macdonald’s original telling of the joke is my favorite joke of all time — proof here — so I saw it coming with Shane’s setup. It was a cool and touching idea (for probably very few of us). For Gillis, it was personal. (Macdonald died in 2021.)

Norm, the ultimate comics’ comic, was famously fired from SNL: Weekend Update in January 1998 after repeatedly making jokes about O.J. Simpson, a close friend of NBC’s west coast president Don Ohlmeyer (who died in 2017). The official reason given was “low ratings,” Macdonald relayed at the time, but very few people bought that explanation. Jim Downey, who co-wrote much of the O.J. material, was also let go from the program. Macdonald was brought back as host in 1999, and Downey returned to the writers room in 2000. Their SNL tenures were far, far longer than Gillis’.

Mere months after Macdonald’s SNL demotion (he stayed on as a general cast member for a very short bit after), the Dirty Work star hosted the ESPY Awards. That year’s Heisman winner was Woodson, the first-ever defensive player to win the highest collegiate-football individual honor. Less than three years prior, Simpson, the star University of Southern California running back and 1968 Heisman winner, was controversially acquitted of murder in the deaths of his ex-wife Nicole Brown-Simpson and Ron Goldman, a server at Mezzaluna Trattoria. Though the Heisman Trust never actually revoked Simpson’s trophy — a common misconception that almost happened — it had been removed from USC’s Heritage Hall lobby after Simpson’s arrest (and then later put back on display, and then stolen.) Simpson would soon be found liable for their wrongful deaths in a civil suit that followed.

That is the environment in which the joke happened. It was perfect, it was vengeful, and it was hysterically funny. Also, it was almost 30 years ago, before most of the athletes at Wednesday’s ESPY Awards were even born. Gillis’ retelling of the joke was great in theory, but in execution, its lack of context made things a bit awkward for the room. And that pretty much sums up the 2025 ESPYs monologue.

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