How Questlove Pulled Off the Grammys’ Crowd-Pleasing Hip-Hop Tribute

Will Smith, once known as the Fresh Prince, couldn’t make it. Lil Wayne and Future dropped out at the last minute. Countless other rap luminaries were never even invited, owing to inevitable time and scheduling constraints. Yet with a climactic, decade-spanning, region-representing, 15-minute medley on Sunday night, the Grammys managed to do something that had proved a struggle for the show since 1989: It pleased hip-hop fans.

Putting Grandmaster Flash next to GloRilla, LL Cool J alongside a TikTok-dancing Lil Uzi Vert, and DJ Drama on the same stage as Flavor Flav, the producers of the show celebrated the forthcoming 50th anniversary of the first hip-hop party with a fittingly sprawling and unwieldy tribute that mixed deep cuts with pop smashes and recognizable icons with overlooked innovators.

“It was a lot of mountains to move to make this happen,” said Questlove, the drummer of the Roots and a go-to rap ambassador for mainstream America, in an interview a few days before the show.

Tapped around Christmas by the Grammys as a curator, D.J. and connector for the centerpiece segment, Questlove, 52, a superfan above all else, knew more than most the deep resentment that many hip-hop legends feel toward the Grammys, after years of perceived disrespect.

“It took a lot of cajoling for this particular generation to come to a function that has systematically treated them as stepchildren,” he said.

Multiple acts who ended up onstage, including LL Cool J, Salt-N-Pepa and DJ Jazzy Jeff, were even part of the inaugural class of hip-hop artists who in 1989 boycotted the first Grammy ceremony to include a rap award, because it was not being televised, which they called “ghettoizing” at the time.

“I explained to them all that I understand the historical significance of it,” Questlove continued, “but you’ve got to understand that there is a new generation that has a seat at the table. Our job is to make it right.” He recalled telling his idols, “I know this reeks of a lot of overcompensatory acts, but just trust me, the old guard is gone and the new guard is the establishing guard. What should’ve been due to you 35 or 40 years ago is coming to light now.”

And it worked — almost across the board. There were the “major coups,” Questlove said of booking LL Cool J, Queen Latifah, Method Man and Ice-T, each of whom is currently starring in a television show. Grandmaster Flash, at Questlove’s rap-nerd insistence, worked his old-school drum machine (or “beat box”) in addition to the record-scratching he is better known for. And they locked in Lil Uzi Vert for the youth-oriented grand finale with a personalized phone call last week.

“Probably the greatest coup of all was getting Missy ‘Misdemeanor’ Elliott, who is world famous for the word ‘no,’” Questlove added, comparing his persuasion techniques to “damn near Jerry Maguire levels.”

Smith — who has hardly appeared onstage, let alone on live TV, since slapping Chris Rock at the Academy Awards — had planned to be there, too. “Will Smith was all of 99.4 percent in,” Questlove said, but the actor was due on set for “Bad Boys 4.” The drummer had suggested that Smith take it all the way back to DJ Jazzy Jeff & the Fresh Prince’s “Brand New Funk.”

Even Public Enemy bought in. The group that once forcefully declared its lack of interest in a “goddamn Grammy,” on “Terminator X to the Edge of Panic,” appeared onstage, although they were asked not to perform that particular track. “That’s the one battle I lost,” Questlove said of the song. (Ice Cube, formerly of N.W.A, was also not available for a “___ Tha Police” moment, Questlove added.)

Of course, some artist absences were more glaring than others. There was no MC Hammer, Puff Daddy, Lil’ Kim, 50 Cent, Eminem, Nicki Minaj, Kendrick Lamar, Kanye West or Drake, who has taken to boycotting the show himself. (Jay-Z, who rapped along from the audience, performed later in the show with DJ Khaled instead.) But this was always going to be the case.

“I knew that 12 minutes to tell a 50-year story was going to be tricky,” Questlove said, fondly recalling the “‘12 Angry Men’-esque battle” that took place with the producers Jesse Collins and Fatima Robinson. “But with my generation of hip-hop, it always starts with the lists and the debates — that’s the fun part.”

On the telecast, LL Cool J got ahead of those criticisms from the outset. “We wish we could have included every single hip-hop artist from 1973 to 2023 — I know, I know, I know,” he cautioned. (Harvey Mason Jr., the chief executive of the Recording Academy, said in an interview that a “full two-hour celebration” of hip-hop, hosted by the Grammys, was being planned for August.)

Those who did take the stage, including Run-DMC, Rakim, Big Boi of Outkast, Busta Rhymes and Lil Baby, needed to represent not only the various eras of hip-hop, but also its regionalism, Robinson, the producer and veteran choreographer, said in an interview.

“I started dancing in the clubs around ’88, ’89, and we never would’ve thought that hip-hop — that I — would still be here doing this,” she said. “I thought I was doing this as a hobby, it was a fad. But I never knew I would make a career out of it. I’ve known Puff since he was a D.J. at a club and drove a beat-up Jetta. I’ve known Jay-Z since he was Big Daddy Kane’s hype man and we performed on high school football fields because we didn’t even have a venue.”

“It is American culture, hip-hop,” Robinson added. “I think people showed up for that.”

Still, only two rap albums have ever won the Grammy for album of the year, with the last coming nearly two decades ago, in 2004, when Outkast took home the top prize for “Speakerboxxx/The Love Below.” And while a single joyous genre survey may not heal all lingering wounds between the Recording Academy and Black artists — especially after a night that ended with Beyoncé losing her fourth best album trophy to a fourth white artist — the leadership behind the Grammys wants everyone to know they are working on it.

“This show, and this hip-hop 50th anniversary segment, is a celebration of that genre of music, but it’s also an acknowledgment that we’ve come a long way as an academy,” Mason said ahead of the Grammys. “We haven’t always honored that genre of music properly or accurately. But that was then — this is now. It’s a new day, it’s a new academy.”

“What we’re doing,” he added, “is we’re trying to be better.”

The full set list:

Black Thought introduction

Grandmaster Flash, “Flash to the Beat”/“The Message”

Run-DMC, “King of Rock”

LL Cool J and DJ Jazzy Jeff, “I Can’t Live Without My Radio”/“Rock the Bells”

Salt-N-Pepa, “My Mic Sounds Nice”

Rakim, “Eric B. Is President”

Chuck D and Flavor Flav of Public Enemy, “Rebel Without a Pause”

Black Thought and LL Cool J interlude, “El-Shabazz (Skit)”/“Rump Shaker”

Posdnuos of De La Soul, “Buddy”

Scarface, “Mind Playing Tricks on Me”

Ice-T, “New Jack Hustler (Nino’s Theme)”

Queen Latifah, “U.N.I.T.Y.”

Method Man, “Method Man”

Big Boi of Outkast, “ATLiens”

Busta Rhymes, “Put Your Hands Where My Eyes Could See”/“Look at Me Now”

Missy Elliott, “Lose Control”

Nelly, “Hot in Herre”

Too Short, “Blow the Whistle”

The Lox and Swizz Beatz, “We Gonna Make It”

Lil Baby, “Freestyle”

GloRilla, “F.N.F. (Let’s Go)”

Lil Uzi Vert, “Just Wanna Rock”