As one of the most iconic and enduring hip hop groups, The Roots have a reputation for their distinctive sound, blending together hip hop, jazz, and soul to create something that is truly unique.

However, it may come as a surprise that the group once found themselves in the middle of a heated feud with none other than The Notorious B.I.G. himself. The Roots’ drummer, Questlove, spilled the story on the Juan Epstein podcast alongside Chris Rock, revealing that “not all was good between The Roots and Biggie” at the time.

In the early years of their career, The Roots were relatively unknown, but they had one very famous supporter in The Notorious B.I.G. He was a huge fan of the band and went out of his way to support them whenever he could. Questlove said, “Biggie was like our biggest champion. When he did Ego Trip magazine he championed us and Jeru higher than anyone. He put Brooklyn onto The Roots.”

However, things took a sour turn when The Roots released the video for their song “What They Do.” The video was a sarcastic take on the rise of champagne culture and the growing divide between the haves and have-nots. Questlove said that while they didn’t intend to directly reference someone’s video, they ended up making a video that was similar in style to Biggie’s “One More Chance.”

“We told the director we don’t want to do a direct reference to someone’s video,” Questlove said. “We just talking about the impending lurking of this new — at the time it seemed like the new apartheid — the have-nots versus the haves. Based on the way the set looked, we didn’t know we were doing a direct reference to ‘One More Chance.’ So, when we saw the final cut, they showed it to us and I was like ‘Oh, damn.’ But it was too late.”

The video caught Biggie’s attention, and he felt that The Roots were taking a direct jab at his work. Questlove said that Biggie commented in The Source that he had been disrespected by The Roots, and the situation quickly spiraled out of control. When The Source reached out to Questlove for a comment, he offered instead to write an op-ed fully explaining himself. However, the next day, Biggie was killed.

Questlove: I said, let me do an op-ed. What I wanted to do was kind of explain the dangers, New York was kind of becoming divided by the haves and the have-nots and I wrote this beautiful manifesto. It was like a 1,000 pages. I faxed it to The Source, and literally, I called The Source. It took me 10 hours to do it. Proofread it. It was great. Called The Source and said ‘Okay, I’m ready to send the response-to-Biggie op-ed.’ And they’re like ‘Oh God, you didn’t hear what happened did you?’ And I was like ‘What are you talking about?’ They said ‘Biggie’s dead.’ And that killed me. I never made it right.”

Questlove: The Roots & Notorious B.I.G. ‘Never Made It Right’ Before Biggie’s Death | Billboard

While the beef between The Roots and The Notorious B.I.G. was short-lived, it is a reminder of how easily misunderstandings and miscommunications can lead to feuds between musicians. In the end, Questlove regrets that he never had the opportunity to make things right with Biggie. “I would have loved to have that sit down,” he said. “I would have loved to have cleared the air, but unfortunately, it never happened.”

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