What It Takes to Make Shane Gillis Funny

March 2, 2025, 1:42 PM ET

The moment Shane Gillis walked onto Saturday Night Live’s stage last night for his second hosting gig, he seemed to know the audience was not on his side.

Gillis arrived with history. In 2019, he was hired as a featured cast member but promptly fired after it came to light that he had used racist and homophobic slurs in his podcast. Instead of becoming a footnote in SNL history, Gillis transformed into a successful standup with a Netflix deal and a Bud Light ad campaign. About a year ago, he was invited to host SNL for the first time—an appearance in which he awkwardly acknowledged the strangeness of the situation, showing a touch of contrition.

This time, the tentativeness was mostly gone. After opening with some politically mild, middle-of-the-road jokes—poking fun at both Joe Biden’s age and Donald Trump’s “fifth-grade-level ideas” about trying to annex Greenland—and acknowledging the audience’s likely biases (“You guys are pretty liberal”), he swerved. “Now I’m going to lose you even more,” he said. He launched into a thread about “a thing I’ve noticed that white guys do.” At some point, he said, white guys can’t help asking their girlfriends: Have you ever had sex with a Black guy? Before posing the question, Gillis seemed to attempt to preempt criticism, suggesting that he understood the exoticizing subtext embedded in the question. “It is racist,” he said, gesturing as if to punch anyone who’d dare to say such a thing. He also copped to having asked the question himself. Once, he said, a woman he was dating told him she’d found his friend “Jamal” handsome—after which Gillis worked up the nerve to ask, Have you ever…? Her response: “Ew, no.” To which he replied, “Jesus Christ, what are you, racist?”

The twist was meant to absolve Gillis: After saying something racist himself, he found someone even more racist than he was. You might read the joke as Gillis’s attempt to poke fun at himself. But from a pure comedy standpoint, the joke was just basic—and unfunny. (“I’m not the worst of them” is hardly a winning punchline.)

Gillis had other groaners. While discussing how much he loves Ken Burns’s documentary series The Civil War, he asserted that “it’s Kryptonite to women.” Put it on, he riffed, and they’ll fall asleep instantly. Setting aside that I know plenty of women who like Burns’s work, it’s pretty hard to find anything funny in what Gillis said next: “That’s a little Cosby tip for you.” Translation: If you want to sexually assault a woman—as dozens of women have credibly accused the comedian Bill Cosby of doing (Cosby has denied the allegations)—put on a historical documentary, because it’ll induce women to pass out from boredom.

Like any stand-up, Gillis is playing a part. His happens to be that of the boorish, conservative-leaning white dude. But his monologue fell flat because even when he pretends knowingness, his jokes are ultimately directed to other boorish, conservative-leaning white dudes. He’s not doing anything to really bring the rest of the audience along.

Gillis’s act went over better in the context of the night’s sketches. You could see hints of how he might have figured into the show had he stayed on as a full-time cast member. In the parody ad “CouplaBeers,” he portrayed a disaffected suburban officeworker who treats his anxiety and depression with a medication that’s just, well, a couple of beers. The sketch worked as a takedown of both TV pitches for prescription drugs and the guy who drinks to quell his pain while causing harm to those around him.

Similarly, Gillis’s persona was well used in “Mid-Day News 2,” a reprisal of a sketch from Phoebe Waller-Bridge’s SNL appearance in 2019. Ego Nwodim and Kenan Thompson once again played Black news anchors who become overjoyed when the alleged perpetrators of the crimes they’re reporting on turn out to be white. Gillis and Heidi Gardner played white anchors who get in on a “game” in which the anchors rack up points depending on the crime suspects’ race. The premise worked even better with Gillis than with Waller-Bridge, in part because of Gillis’s history, and in part because the sketch offered a bit of social commentary that implicated everyone in the joke.

That was a key distinction between Gillis the sketch collaborator and Gillis the stand-up. Alone on stage, left to his own devices, he fell into the schtick of being crass for crassness’s sake. When he slipped into fictional character—and allowed SNL’s writers to take the reins—that’s when the commentary came closer to hitting its mark, and when he finally earned some chuckles.

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