The famous cartoon that led Questlove to befriend Jay-Z: “It’s so weird”
Questlove and Jay-Z seem like unlikely musical collaborators. While Questlove is an instrumentalist who came to fame by making soulful conscious music as part of the roots, Jay-Z is an emcee who exploded into the mainstream by captivating the culture with his bravado and slick lyricism.
That said, at the turn of the millennium, the two artists collaborated, became close, and, according to Questlove, initially bonded over their love for a particular cartoon.
During an interview, Questlove explained that Jay-Z’s love for The Simpsons played a part in them becoming friends and helped him realise that he had more in common with the Brooklyn icon than he had initially thought.
Reflecting on how he first crossed paths with Hov, Questlove explained that it was in the early 2000s when The Roots signed with Def Jam—Jay-Z was the president of the record label at the time. During the early 2000s, there was still a divide between different kinds of rappers, whether you were a conscious emcee, a mainstream act or a gangster rapper; according to Questlove, there were noticeable groupings.
Explaining this, Quest told Fader, “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.”
However, the Roots producer unveiled that after the September 11th attacks in New York City, he found solace in Jay-Z’s album The Blueprint, unveiling, “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!'”
Still, the filmmaker really wanted to tell Jay-Z about Questlove’s positive response to the project. Recalling her desperation, Questlove remembered, “She was 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.'”
Hampton eventually told the Reasonable Doubt creator, and the Brooklyn rapper appreciated him so much he ended up inviting The Roots drummer to a show he was doing in Philadelphia, and called his cell phone several times.
Jay-Z invited Questlove to the studio, and, although Questlove had assumed Jay-Z was an arrogant commercial rapper, he was quickly proven wrong, and the two bonded. Recalling when Hov shocked him, Questlove told Fader, “He disarmed me in two minutes. He doesn’t remember this but 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. And I was like, ‘Yo, he’s a nerd. He’s like me.’ I was amazed.”
After speaking with Jay-Z and relaxing with him in the studio, Questlove realised that he was a “regular guy.” Reflecting on his epiphany, the Organix creator emphasised, “He was a complete sponge, and that’s when I realised 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.”