By the time Sheryl Underwood took the podium Sunday night halfway through the live Roast of Kevin Hart on Netflix, the stage was set for a memorable rebuttal. Despite being one of the least recognizable faces on a dais that included celebrities like Chelsea Handler and Pete Davidson, Underwood had consistently been the target of some of the night’s sharpest barbs, including the first truly pearl-clutch-worthy joke of the night, courtesy of host Shane Gillis. “Sheryl’s husband killed himself,” Gillis said. “Apparently Black does crack if its married to Sheryl and jumps off a fucking roof.” While nothing is off-limits in the context of a roast, the line felt especially harsh given many were unfamiliar with her tragic story — unlike, say, the night’s many jokes about Davidson’s firefighter dad dying during 9/11.
Adding to the weight of the moment, Underwood followed Tony Hinchcliffe, a comedian best known in the mainstream for calling Puerto Rico a “floating island of garbage” while stumping for Donald Trump during the 2024 election, and on this occasion, Hinchcliffe leaned into his heel persona by trying to out-provoke everyone else on the lineup. “The Black community is so proud of you,” he said to Hart to close his set. “Right now, George Floyd is looking up at us all laughing so hard that he can’t breathe.” His take-no-prisoners approach played well. “A lot of people wanted him to fail, and he just fucking killed,” Gillis summed up the mood in the room following Hinchcliffe’s set.
But when Underwood got on the podium, the room’s atmosphere reset. “First of all,” she said, addressing Hinchcliffe directly, “you think you hurt my feelings by talking about my dead husband? My husband only died once. You die every night with them wack-ass jokes you be telling.” She also hit back at Gillis for his various jokes walking racial lines: “You may talk some shit about me, but I know your kind. You want to hit this Black pussy harder than you hit the windows of the Capitol on January 6.” Crucially, she played by the roast rules, which made her rejoinders hit even harder. She explicitly praised the event for demonstrating that “freedom of speech is alive today.”
Her set was a triumph, in part because her energetic delivery injected life into the proceedings after the show had slipped into a monotonous rhythm halfway through its bloated, nearly three-hour runtime. But more than that, she found a new way to create stakes for her jokes after every other panelist had exhausted every other type of provocation. There are only so many times one can see Handler called a “whore” or Hart mocked for his height in the span of one show before it grows tedious. Underwood, instead, got great mileage out of focusing on her own sexuality and sexual experiences. She reminisced on tongue-kissing audience member John Stamos while she hosted the show The Talk, asked panelist Draymond Green to prove he’s a bully by inviting him to “beat this pussy up,” and then finally turned her sights to the man of the hour. “Kevin and I hooked up once before he got married,” she said with enough hesitation to sell the audience on the idea that it might be true. “Kevin Hart is packing ten inches in his pants. They’re his legs. But it’s still ten inches.” She continued, “Fucking Kevin was a lot like watching his movies. The first five minutes are okay. Then you’re just waiting for it to be over.”
In an event that featured surprise appearances from Venus and Serena Williams, Hart enemy Katt Williams, and the Rock, no one got an ovation like Underwood following her set. The dais and the crowd stood and cheered in appreciation, and the camera cut to a shot of Tracee Ellis Ross in the audience literally breathing a sigh of relief. The reaction called to mind one of the jokes from Underwood’s set. “I know you want to fuck me,” she said to Gillis, following her January 6 barb. “Because you’re tired of fucking your sister. So you want to fuck a real sister.” Underwood added that she might actually consider it, given she’s currently on a tour titled “I Need a Job.” After her performance on Sunday night, her tour is going to need a new name.
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