Dave Chappelle has never lost Best Comedy Album at the Grammys, and this year could tie legends Carlin and Pryor

Daniel Montgomery
·3 min read
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Dave Chappelle has four previous Grammy nominations for Best Comedy Album and four previous wins: “The Age of Spin and Deep in the Heart of Texas” (2018), “Equanimity and The Bird Revelation” (2019), “Sticks and Stones” (2020) and “The Closer” (2023). Indeed, he’s undefeated in the category and is a contender again this year for “What’s in a Name?” If he prevails again he’d tie for second place on the all-time list of winners in the category.

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To date the biggest winner for Best Comedy Album is the now-disgraced Bill Cosby. He claimed six in a row from 1965 to 1970, and then won a seventh in 1987. Of the five comedians who are next in line, Chappelle is the only one still living. The late George Carlin and Richard Pryor won five apiece, and Chappelle shares fourth place with fellow quadruple winners Peter Schickele and Robin Williams.

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But according to the combined predictions of Gold Derby users, Chappelle is an underdog for the award this time around. Instead, the favorite to win is Trevor Noah for “I Wish You Would.” Noah has never won before, and this is only his second nomination following a bid for “Son of Patricia” in 2020. Notably, though, this is the first time Noah has been nominated since he started hosting the Grammys telecast; he has done so for the last three years in a row, and he’s back for a fourth round in 2024, which could inspire Recording Academy members to give him their grateful votes of support.

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Chappelle is also a divisive figure due to his jokes about the LGBTQIA+ community, specifically transgender people. But the Grammys have recently doubled down on their support of controversial comics. Chappelle’s last victory was for “The Closer,” the very special that was criticized by the queer community. The year before, Louis CK won for “Sincerely,” his first comedy special following his admission of sexual misconduct at the height of the #MeToo movement. Whether awards voters support these comedians in spite of or because of their controversies is anybody’s guess.

Though if voters want to embrace controversy, they could always opt for Chris Rock‘s aptly titled “Selective Outrage,” in which he addressed the infamous incident where Will Smith slapped him on live television at the Oscars. Rock is also a darling of the academy, having won three times over the course of his career. However, the only other time he has gone head-to-head against Chappelle, in 2019, Chappelle won. So can Rock make a comeback? Will Chappelle continue his winning streak? Or will Noah be crowned for the first time? Our odds indicate it’s between those three, with the remaining two nominees — Wanda Sykes (“I’m an Entertainer”) and Sarah Silverman (“Someone You Love”) — fighting for an upset.

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