The Roots also have an extensive history with Jay-Z, having rode shotgun as his backing band on the critically acclaimed live album, 2001's Jay-Z: Unplugged. The rap legend returned the favor by signing the group to Def Jam in 2005 after Jay-Z became president of the historic hip-hop label.

In reflecting on their decades-long relationship, Questlove praised the 4:44 rapper, insisting that “people who are really successful are open.”


“Jay’s a guy where it’s like, ‘Okay, let’s try this idea. Let’s try this idea. Let’s try this idea.’ He’s open to all ideas and what sticks,” he said. “That’s what works. That’s what we go with. You know, that’s how we forged our relationship.”

Questlove also attributed his signature style to “a bold change in direction.”

“[It’s] one of the toughest things an artist can do, especially when you’ve just broken through to the mainstream,” he said. “I mean, it’s the musical equivalent of burning a bag of money.”


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