According to Questlove, it was Jay-Z making a Simpsons reference during their first conversation with each other that led to the relationship they have to this day.
In his appearance on the Fader Uncovered podcast, Quest recalled how the beloved animated series helped him realize he and Jay had more in common than he thought. While speaking with host Mark Ronson, Quest gave some backstory on how The Roots ended up on Def Jam when Jay was president of the label, with it all beginning with Jay’s 2001 The Blueprint album.
“It’s so weird. In 2001, there was still this hip-hop apartheid, church and state separation thing between artists. Backpackers didn’t take kindly to commercial rappers. Commercial rappers looked at us like broke haters,” Quest said, before recounting how he told dream hampton that he liked the album.
“What’s weird is for a lot of people, September 11 is the day where a lot of us just self-soothed to The Blueprint by just listening to it over and over and over again, just to get our minds off of what was happening. I hit up dream hampton. I was like, ‘Yo, don’t tell nobody, but I think this Blueprint record… but don’t tell no one,'” he recalled. “She’s like, ‘Ahmir, you got to let me tell Jay this.’ I said, ‘No, no, no, no, no.’ Because to my mind, he’s like, ‘Oh, he’s the devil, commercial rapper.’ It’s like, ‘No, no, no, no, don’t do that.’ She’s like, ‘Ahmir, I got to get you out your own way. I’m telling Jay this, and you’re going to accept it.'”
So, dream ended up telling Jay, and the Brooklyn rapper appreciated that Quest liked his record, leading to him inviting The Roots drummer to a show he was doing in Philly, as well as calling him after dream gave Jay Quest’s number.
“He called a few times and I wasn’t answering and [dream] hit me up like, ‘Why aren’t you answering the phone, Ahmir? Just talk to him,” he said. “And finally I gave in.”
“He disarmed me in two minutes,” Quest continued. “He doesn’t remember this. He made a Troy McClure Simpsons reference. It was either a monorail reference… it wasn’t Lisa needs braces, but it was a deep Conan-era Simpsons reference that he made. … I was like, ‘Yo, he’s a nerd. He’s like me.’ I was amazed.”
In speaking with Jay, Quest realized that the rapper was a “regular guy,” while also speaking to what makes Jay so successful.
“He was a complete sponge,” Quest said. “And that’s when I realized that people who are really successful are open. They let everything in…Jay’s a guy where it’s like, ‘Let’s try this idea. Let’s try this idea.’…That’s how we forged our relationship.”
Elsewhere in the interview, Quest talks about how Dr. Dre helped save The Roots’ career, the infamous Electric Lady Studios recordings, and more.