Shane Gillis’ 10 Best Jokes at the ESPY Awards (Critic’s Picks)

“There’s one thing I want to say before I get out of here, and this is a dumb joke, you guys aren’t going to like it — it’s just a Norm Macdonald joke that I loved when he hosted the ESPYS [in 1998] and I’m going to do it now,” Gillis said. “[Colorado Buffalo] 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. In which case, they can take that away from you.”

Sportsplainer: Although O.J. Simpson was acquitted in criminal court of the 1994 murder of his ex-wife Nicole Brown Simpson and her friend Ronald Goldman — who was a waiter — in 1997, a civil trial found him liable for their deaths, and the Heisman he won in 1968, was auctioned off to help pay for the more than $33 million that was award to the victims families in compensatory and punitive damages.

It’s also worth noting that Macdonald, who died in 2021, is a hero among comics for his deadpan, unflinching comedy, which during his stint as Saturday Night Live‘s Weekend Update anchor often included him referring to Simpson as a “murderer” with no “alleged” attached. The same year that Macdonald hosted the ESPYs, Don Ohlmeyer, the president of NBC’s West coast division, removed Macdonald as Update anchor, citing declining ratings. Macdonald alleged, however, that the real reason had to do with Ohlmeyer’s friendship with Simpson.

“It’s crazy to be in this room with so many legends,” Gillis said. “Sugar Ray Leonard’s here, hell yeah. Sugar Ray, you’re the man, but in 10 years, Jake Paul’s gonna try to knock you out, so take it easy.”

Sportsplainer: A number of the 28-year-old social media star-turned-boxer’s fights have pitted him against Paul’s last two fights pitted him against aging pugilists born in the 1980s (Tyron Woodley), ’70s (Anderson Silva) and even ’60s (Mike Tyson), which some attribute to his 12-1 record. Leonard was born in 1956, a decade that Paul has yet to exploit.

“Four-time WNBA all-star Brittany Hicks is here. Give it up for Brittany, everybody. I’m joking around, that’s my friend’s wife. I knew none of you knew WNBA players. That’s crazy you [clapped for] it.”

Sportsplainer: Despite a surfeit of press reporting that the WNBA now enjoys the same level of popularity as the male version, Gillis’ joke may have proven otherwise. The crowd did give it up, mildly, for Hicks, but she’s the wife of his comedian friend Matt McCusker and not in the WNBA.

“Shedeur Sanders had his jersey number retired at Colorado this year, and people are saying it’s because of nepotism, because of his father, and it’s not. It’s because he went 13 and 12 over his career and he almost won the Alamo Bowl. Definitely not nepotism, right?”

Sportsplainer: Sanders wasn’t in the ESPYs audience, which was probably a good thing. He’s already endured plenty of jibes for being a fifth-round draft pick (by the Cleveland Browns) after much speculation that he was destined to be chosen in the first. That was followed by conjecture that his father, Deion Sanders, who coached his son’s team, the University of Colorado Boulder’s Buffaloes during the two seasons he was there, had hurt Shedeur’s prospects by over-hyping him behind the scenes.

The school’s decision to retire Shedeur’s jersey after just two seasons also proved controversial given his stats, and because former Buffaloes QB Darian Hagan, who had a 28-5-2 record and took the team to the national championship in 1990, has not had his jersey retired. To be fair to Shedeur, the Buffaloes went 1-11 the season before he arrived, and he has broken over 100 school records. (And his actual win-loss record is 13-11.)

“Caitlin Clark, she and I have a lot in common. We’re both whites from the Midwest who have nailed a bunch of threes.”

Sportsplainer: Although Clark’s 29% WNBA three-point basket average is down from the 34% she posted last year, she remains near the top of the competition and will participate in the three-point contest that takes place July 17 during the upcoming WNBA All-Star Weekend. Gillis’ was talking about a different kind of scoring when he referenced himself, which resulted in some wincing and murmuring from the crowd. But as he said in response, “Lighten up a little, this is not serious.”

“Skip that joke. Please skip that joke. All right bring it back. I‘ll tell that joke. I didn’t write this. ‘Put Your Hands Where My Eyes Can See,’ is what they say when DeShaun Watson gets a massage.” 

Sportsplainer: This one ranks high for sheer ballsiness. Gillis made the joke — which name-checks the title of a Busta Rhymes track — following Rhymes performance on the show, and the audience sounded like it had been punched in the gut. The reason: Beginning in 2021, more than 20 women filed civil lawsuits accusing the former Houston Texans quarterback of sexually inappropriate conduct or sexual assault during massages. (In 2021, Watson wrote on X that he had “never treated any woman with anything [other] than the utmost respect.” and settled most of the suits.) “I disagree as well,” Gillis said with a smile when he heard the reaction. “I swear to god I didn’t want to tell it.” But he did.

“Aaron Rodgers didn’t take the [Covid 19] vaccine because he predicted it would be bad for him. And then he joined the New York Jets. So maybe he wasn’t right about everything.”

Sportsplainer: Rodgers sat out his first season with the Jets after suffering an Achilles injury in the first game. During the 2024 season, he led the team to a dismal 5-12 record and was released early this year. He is now with the Pittsburgh Steelers.

“Joe Rogan actually wanted me to be here to host this award show so that I could capture [NBA Commissioner] Adam Silver because Joe thinks he’s an alien. And Donald Trump wanted me to be here to capture Juan Soto for the same reason.”

Sportsplainer: Actually, this was more of a political joke about the Trump administration’s reportedly indiscriminate arrests of immigrants than a poke at the New York Mets’ Dominican outfielder, whose $765 million contract is the largest in sports history.

“Donald Trump wants to stage a UFC fight on the White House lawn. The last time he staged a fight in D.C., Mike Pence almost died,” Gillis said. “Actually, there was supposed to be an [Jeffrey] Epstein joke here, but it got deleted. Must have probably deleted itself, right? Probably never existed, actually. Let’s move on as a country and ignore that.”

Sportsplainer: An even-more-timely Trump joke about the U.S. president and his administration’s backtracking on its promises to reveal all about the late sex offender Epstein, which has sparked a firestorm of criticism from the MAGA media and the commander-in-chief’s conspiracy-minded supporters, who are convinced there exists a list of powerful figures who joined Epstein in sexually abusing minors, and that the financier did not commit suicide in prison but rather was murdered.

“Shohei Ohtani couldn’t make it tonight. Man, I hope his interpreter didn’t bet that he was going to be here. Shohei is a once-in-a-generation talent. No one’s been able to do what he does at so many positions. Pitcher, hitter and bookie. A bookie is what Bill Belichick reads to his girlfriend before bedtime. They do. They read, uh, The Very Horny Caterpillar, The Little Engine That Could But Needed a Pill First, and of course, the classic Goodnight Boobs.”

Sportsplainer: “That was my favorite one,” Gillis said after telling the joke, and the burst of laughter that came back to him said the audience agreed. The Ohtani lead-in was a throwaway reference to the Los Angeles Dodger phenomenon’s interpreter, who was sentenced to nearly 5 years in federal prison for stealing $17 million from the Major League superstar and using the ill-gotten gains to place illegal bets.

The punchline that killed was Gillis’ reference to the 73-year-old former head coach of the New England Patriots (now guiding the University of North Carolina’s football team) and his new 24-year-old girlfriend, former cheerleader Jordon Hudson.