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Questlove Remembers His ‘Surreal’ Dinner With O.J. Simpson

On this week’s installment of his Pandora podcast “Questlove Supreme,” Roots drummer and “Late Show” bandleader Ahmir “Questlove” Thompson and his crew talk with “Daily Show” veteran and “Last Week Tonight” host John Oliver, who speaks at length about the challenges of putting together topical comedy, about his first-ever trip to a Walmart and why it was his most profound cultural clash in coming to America, and perhaps most entertainingly, of how he ended up hosting “The Daily Show” for several weeks in 2013 when Jon Stewart went on hiatus to make the film “Rosewater.”

“It was terrifying,” Oliver recalled. “Because he called me and said, ‘I’ve got that movie I’ve been working on. I’m going to direct it.’ So I was kind of, ‘Oh, that’s nice’ — I didn’t see what was coming. I said, ‘Well, that’s an odd thing, to decide to call me– how many people are you calling today?’ And then he said, ‘So I’m going to be gone for a few months. Will you host the show?’ So I just said, ‘Yeah, I’ll do whatever you want.’ And then hung up the phone and went, ‘Oh, sh–!’ I just said yes because I would just say yes to anything he ever asked me. But I did not think about what I’d just said yes to until I put the phone down.”

Yet the most memorable part of the interview is probably Questlove recalling a dinner he once had with O.J. Simpson — it’s a story he’s told before, but never in quite this much detail. Oliver initially thinks he’s joking, but then Quest continues [the passage has been edited for flow]:

“Seriously, I had dinner with O.J. one night. It was the surrealist thing in my life. We were in Miami working on an album. And [producer/former Roots keyboardist] Scott Storch and some friends of his are also connected to O.J. They go golfing with him and everything. So I guess the story is that one of their wives was having a birthday dinner. And Scott just ever so casually mentioned, like, ‘Let’s go on a dinner break. Oh, by the way, O.J.’s going to be here, too.’ And [off to the side of the main dinner table], there’s this small table. And it’s me, Busta Rhymes, Scott Storch, and O.J. Simpson.

“In the beginning it was slightly awkward,” he continues. “I tried to act as normal as I could. And he was like, ‘Yeah, I used to have one of those.’ He was pointing at my afro and stuff. And then four bottles of wine in, he says to Busta, me, and Scott, he’s like, ‘You know Hurricane Carter? All the singers, Bob Dylan and them, they fought for Hurricane Carter’s innocence. And you know, I need the rappers to make a song about me!’ And we’re all looking at each other [laughter].

“There was a point where he started talking about [prosecutors Christopher] Darden and Marcia Clark and stuff, and then me and Scott’s brother were having that ‘Trading Places’ bathroom stall, feet raised up in the air so no one could see us at the bottom thing. And it was like, ‘Yo, are we allowed to be talking to O.J. about this sort of thing or not?’ It was the weirdest three hours of my life.”

Listen to the full interview here.

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