"In my mind, I was like, ‘now this youngster named Kanye West is going to take over the reigns.'"

In September 2004, Dave Chappelle threw a block party in Brooklyn that was turned into an aptly titled documentary, Dave Chapelle’s Block Party, the following year.

Inspired by the 1972 Wattstax benefit concert commemorating the seventh anniversary of the Watts riots, the block party featured performances from conscious rap and neo-soul favorites like Common, The Roots, Mos Def, Talib Kweli, Erykah Badu, Fugees, Bilal, Jill Scott and dead prez.

What should have been a celebration of the Soulquarians movement he masterminded, however, felt more like a funeral for Questlove. What he saw was the passing of the “alternative hip-hop” torch he had carried for the last decade to a new generation specifically, a new leader named Kanye West.

“That morning, I was like, ‘ugh, this is how it all ends,’” he recalls in a new interview with Alec Baldwin as part of his WNYC series, Here’s The Thing. “Onscreen it looked very beautiful, it looked like a beautiful celebration, but in my mind, I was like, ‘well this is where I once held the baton and now this youngster named Kanye West is going to take over the reigns and he’s going to be the new leader.’”

Questlove also touched on that day in his 2013 book, Mo’ Meta Blues, and remembered how Kanye’s captivating performance at the block party literally made him question The Roots’ future.

We were shooting a performance of “Jesus Walks,” and Kanye wanted to come in with a marching band. I remember a welter of political and artistic thoughts crowding my mind. I thought about how presidential he looked and how the black kids were responding to him, something I had never really focused on in our own audience. I remember having a kind of out-of-body experience and investigation of the thought of my own artistic death. “Am I dead already?” I wondered.

I saw the rest of the plot stretched out before me. Kanye was going to be the new leader, and I was fine with that. I was acting like I knew it was my last day. I took lots of photographs. I said lots of good-byes. I told myself, “You’re not going to get all these people together again."

Questlove was partly right: he didn’t get all those people together again. But Kanye West’s arrival didn’t exactly make The Roots extinct. Since Dave Chappelle’s Block Party, Questo and co. signed to Def Jam, added another five critically acclaimed albums to their catalog and became Jimmy Fallon’s house band. This year, they’re set to release their 17th LP, End Game. The Roots are indeed a legendary crew, even if they don’t always scream it from the rooftop.

“The Roots are more known to be Phish or the Grateful Dead of hip-hop than the winners of hip-hop,” Questlove tells Baldwin. “But don’t sleep: Phish is a group that somehow still makes eight figures a year under the radar. They didn’t have to shake their ass in a video, they didn’t have to get mired in controversy, they quietly sell out Madison Square Garden. That for us was a better way of survival.”

Kanye West, meanwhile, has juggled—rather than carried—that proverbial torch Questlove passed him. The College Dropout established Kanye as "the red-nosed reindeer of the Roc," but what separated him from The Roots is that he was never just a conscious rapper. While Questlove admitted he had “mixed feelings” about working with Jay Z on Unplugged, Kanye relished putting Freeway and Mos Def on the same song. The “first n*gga with a Benz in a backpack,” Kanye West was the bridge that closed the gap between the mainstream and the underground.

“His wolf in sheep’s clothing approach is kinda brilliant,” Questlove says.

Given his increasing investment in other areas like fashion and design, not to mention his budding bromance with Donald Trump, Kanye is no longer the main torch bearer for conscious rap. New leaders like Kendrick Lamar and Chance The Rapper are fighting the good fight today. But what Questlove couldn’t foresee at Dave Chappelle’s block party is how that flame would continue its course through the crowd and into the hands of another young Yeezus disciple who would later become J. Cole.

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By Andy James. You can follow him on Twitter.

Photo Credits: Tumblr / Tumblr