Questlove, drummer and frontman for the Grammy award-winning band The Roots, is back with “a new jump-off,” he laughs, “like it’s 2008,” called Questlove Supreme, a fun, irreverent interview podcast where “legends and legends in the making,” including Usher, Michelle Obama, Weird Al Yankovic, Chaka Khan and more bring “their legacies to life in their own words.” On this episode, he sits down with late-night legend Jimmy Fallon to talk about their top five performances on The Tonight Show, the time Jimmy played ping-pong with Prince, the first mixtape he ever made, and a truly incredible story when Jimmy got to sing with Stevie Wonder. “I hate you for that, man,” Questlove groans.
The Roots has been Jimmy's house band since Late Night, so Questlove and Jimmy are far from strangers. They talk about their mutual fondness for doo-wop music (Questlove blows Jimmy’s mind by pointing out that legendary guitar player Jimi Hendrix originally played for Joey Dee and the Starliters) and loving sleep (Jimmy discovered that Grace Jones still goes out to clubs until five in the morning; “I would have no clue,” he laughs). Questlove has helpful pointers for Jimmy on parenting; when Jimmy shares that his first-grade daughter can’t dance, Questlove tells him to show her Soul Train. “Trust me, a good Soul Train clip...that’s how everyone in America learns how to dance.”
Both of them are music lovers and talk extensively about their childhood growing up with cassette tapes and Columbia House memberships. “Every album back then, I loved it, even if it was bad,” Jimmy says. “I tried every type of genre...like oh, maybe I’m into metal...maybe I should, like, worship the devil.” He laughs. “What was I talking about? I’m an altar boy.” Quest was the master of the mixtape, he says, but though Jimmy made mixtapes, he wouldn’t let anyone keep them. “I thought it would affect the record industry,” he admits, as Quest snort-laughs. “I would have to take my music to the party, I play my mixtape, then I take the tape home. I would own my mixtapes...my sister was like you’re the worst! You’re the weirdest kid!” Sometimes he’d record songs off the radio, especially the novelty comedy songs on Dr. Demento. He remembers writing his own “Manic Monday” parody that was “just awful,” thinking he’d become the next Weird Al.
They share some great memories of hijinks on The Tonight Show and off, like the time Quest messed up the drum solo for Phil Collins’ “In the Air Tonight” because his cymbal fell off (“it, like, broke in pieces,” Jimmy remembers). They also have incredible and somewhat surreal stories about Prince: once, he tricked Jimmy into going onstage during his concert in Madison Square Garden; another time Quest was charged with planning an after-party for him. He scrambled around and secured a club for the venue, loaded in a pool table ("it was a five-story walkup," he says), and was DJing Fela tunes when Prince’s manager told him to put on a Finding Nemo DVD instead. Jimmy once squared off with him over a ping-pong table, not knowing what a big fan of ping-pong Prince was (he owned “a gold paddle,” Quest reveals), and lost. “I go, ‘you won! You won!’...and I turn around, and he’s gone...like Batman,” Jimmy says. Questlove actually ran into him after the match and asked what happened. “And seriously, he's like, ‘Ask your boy,’ and…the [car] window goes slowly up, just like the Grey Poupon commercials...and just takes off."
Get more details about Prince’s ping-pong game, Jimmy’s ridiculous high school rap name, and tons of other great stories from both of these men’s wild lives, on this episode of Questlove Supreme.
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