How Dave Chappelle Became The Biggest Winner Of The Grammys

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The 60th Grammy Awards featured the inclusion of the “Best Comedy Album” award in its telecast, the first such occurrence in the Recording Academy’s history. The award went to Dave Chappelle, an icon whose return to comedy after a controversial hiatus has been nothing short of extraordinary. But Chappelle’s commanding presence during the ceremony extended beyond his acceptance speech and into his time on stage as part of Kendrick Lamar’s opening performance and as presenter for the “Best Rap Album category.”

Chappelle earned the first Grammy for his trophy case for his Netflix specials, Heart Of Texas and The Age Of Spin. While accepting his award, he kept his speech succinct and gracious, shouting out his network and collaborators on Saturday Night Live and Chappelle’s Show. He beat out serious heavyweight contenders including Kevin Hart, Jerry Seinfield and Sarah Silverman (plus Jim Gaffigan, who humorously mentioned he couldn’t wait to see Dave win while he presented an award earlier in the evening). However, it was what Chappelle said in other moments that make him a wild-card pick for the real winner at the Grammys.

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Kung-Fu Kenny opened the evening with the kind of high-caliber performance we’ve come to expect from “the greatest rapper alive.” It was Chappelle’s unannounced appearance mid-set that got Heads talkin’, and his words that had us listening. “The only thing scarier than watching a Black man being honest in America is being an honest Black man in America,” he said, aligning himself with Lamar. Just as quickly as he popped up on stage, he was gone, leaving a palpable sense of gravitas in the room, albeit through laughter. It was fitting for the world’s biggest name in comedy to join the world’s biggest name in Rap at the very top of a ceremony that would go on to tackle gun violence and sexism through live performances.

Chappelle managed to perform yet another Hip-Hop miracle while introducing the nominees for “Best Rap Album.” Before naming the LPs up for consideration, he reminded everyone of his deep love for the culture. By the time the name “Jarobi” escaped his mouth, it was clear Dave was not going to allow the telecast to go on without mention of A Tribe Called Quest, who famously performed last year’s stand-out set for the Grammys. As Heads will probably recall, Q-Tip took to social media to express his anger with the Recording Academy for snubbing We Got It from Here… Thank You 4 Your Service. With that in mind, Dave mentioned each A.T.C.Q. member by name (even adding Busta Rhymes’ affiliate status, “and sometimes Consequence”), making sure to give a heartfelt shout-out to Phife Dawg.

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Whether or not the Recording Academy opted to include “Best Comedy Album” in this year’s telecast strictly because of Dave Chappelle is unclear, but it was certainly a welcome addition to an event often criticized for playing it safe.