The Roots Annual Grammy Jam Thrived Until 3 A.M. Thanks to Dave Chappelle Jokes and Multi-Genre Meld

The Roots
Mark Seliger/NBC

The Roots

With less than 24 hours to go until the Grammy Awards ceremony, and as Clive Davis’s Pre-Grammy Gala was underway across town, another iconic staple of a busy weekend in Los Angeles was unfolding on stage at Live Hollywood: a jam session featuring a universe of stars that revolved around the sun and the light of The Roots.   

“This transcends genre, this transcends race,” Roots vocalist Tariq “Black Thought” Trotter said of the idea of the evening as the festivities kicked off just before midnight in front of an audience of industry professionals and fellow musicians. The proceedings, which is in its 16th year and is concocted by Roots tour manager Tina Farris, are "the real definition of all-inclusive," according to Trotter: the program "transcends point of origin, point of destination.”  

Introduced by Dave Chappelle, who would become an unscheduled MC throughout the night alongside designated master of ceremonies Deon Cole (who cracked jokes during the sometimes lengthy set-ups between guests), The Roots kicked off the jam with the stage all to themselves, running through a range of hits of their own including their 2006 Game Theory track “Here I Come.” It also served as the original theme to their day job playing as the house band for Jimmy Fallon’s Late Night talk show (which they joined since its inception 11 years ago) and seeing it through its eventual transition into its current iteration as The Tonight Show, where the band is frequently on-air fodder.

A jam taking place Grammy weekend wouldn’t be complete without current nominees. The Roots, with Questlove on the drums, James Poyser on keys and “Captain” Kirk Douglas on guitar, characteristically meshed well with the range of artists featured, including (perhaps most surprisingly) Billy Ray Cyrus. Nominated this year for assisting on the remix of Lil Nas X’s 2019 record breaker “Old Town Road” (in the music video, record of the year and best pop duo/group performance categories), Trotter took on the teenager’s rapping duties in lieu of X’s absence, throwing in an improvised line or two for good measure. But Cyrus didn’t launch into “Old Town Road” until treating the audience with a crackling rendition of his 1992 signature “Achy Breaky Heart" -- a former record of the year contender -- proving that versatility of The Roots is virtually unmatched. 

Bookending the show was another Grammy nominee, Gary Clark Jr., who wrapped up the proceedings with a trio of his tracks, including a powerful version of “This Land.” Nominated this year for music video, rock song and rock performance, the rendition of the song proved to be a preview and perhaps quasi-rehearsal for the next day’s Grammy ceremony, where Clark is slated to perform the song once again alongside The Roots. Performed live and propelled by the band, the track had added force, with its hooks accentuating harder and the lyrics landing stronger than perhaps even on his nominated recording. Adding to the cache of the night’s potential Grammy winners, Burna Boy, the Nigerian singer-songwriter, ran through tracks courtesy his fourth studio effort African Giant. Released last summer, it scored a nod for best world music album. 

Both the audience and band seemed most alive when they were grooving. Spanning the generations, Steve Arrington, the frontman for the Ohio funk band Slave, hit the stage with earworms “Just A Touch of Love” (which peaked at No. 9 on the R&B charts in 1979), “Watching You” (a Hot 100 hit which peaked at No. 6 on R&B) and “Weak at the Knees,” a cut which most recently surfaced in the 2015 soundtrack to Straight Outta Compton. It was a guest Trotter specifically seemed giddy at the prospect of sharing the stage with, endlessly grinning while providing background vocals and first welcoming Arrington by singing his praises. “I shouldn’t even introduce this man who’s about to come out,” he said. “Because the brother doesn’t need any introduction if you know these classic joints.” 

Vaulting from the '80s to the modern day and from funk to soul, Ty Dolla $ign also appeared, handling a ruminative version of his 2014 hit “Or Nah,” sans guest appearance by feature Wiz Khalifa. Nonetheless, hip-hop was well-represented throughout the expansive jam, courtesy of appearances ranging from South Los Angeles rapper Duckwrth, BJ the Chicago Kid, the Jamaican reggae artist Chronixx, and Maimouna Youssef (otherwise known as Mumu Fresh). Even Chappelle joined in, at multiple points rapping along to classic cuts the DJ was spinning, including an extended version of the Eric B. classic “Paid in Full,” to which he knew every word.

Despite stage managers visibility trying to move the show along, Chappelle happily stood in their way. With a cigarette hanging out of his mouth while imploring the audience to put down their phones and not record him (“Those could end my career!”), he treated the crowd with jokes and stories, including one about a previous night’s dinner he attended with Cole alongside Eddie Murphy (“It was the first time I ever saw Eddie eat”), and about his experience earlier in the day at the annual Roc Nation Brunch. “I went to Jay-Z’s brunch this morning,” he said. “Jay-Z’s got so much money, he made his own Easter.”

With a guest list this stacked (the backstage area was visibly overflowing), after playing for around two hours straight,  the Roots crew took an extended break around 1 a.m., which resulted in more banter, jokes and stories from Cole and Chappelle. By 2 a.m., Questlove took his perch back at the drumset for another hour of tunes, with the jam wrapping up by 3. Though it was an aside Trotter mentioned at one point that summed up the evening, which spoke not only to the length of the show but the impressive avalanche of the quality of the music music: “This is not for the faint of heart.”