Questlove Talks Jay-Z Advice and the Supergroup with Amy Winehouse That Never Happened

AllHipHop Staff

(AllHipHop News) Many artists who achieve success on the level of fame, money, and chart-topping albums agree that the urge to stray from what brought them to the table can be a challenge.

However, Questlove credits his former Def Jam boss, Jay-Z, for keeping him and his group, The Roots, musically and artistically intact.

"(Jay-Z) didn't want to be known as the bad guy that killed The Roots," Questlove told the Associated Press (AP), while highlighting an ironic difference between himself and the man who signed The Roots. “I told Jay, 'Like man, that would be nice to have all my records debut at No. 1 and stuff.' But he's like, ‘Yeah, but you're just looking at that. I got to deal with beef with this cat and that cat. Every year, some rapper's going to take a potshot and I got to take the gloves out the closet and start training.’ ... [Jay-Z] sees me as an artist making my dream come true. Like, he wants to be seen as a true artist, not the richest guy in Hip-Hop. Meanwhile, I would like 13 zeros in my account.”

While a No. 1 album debut is a worthwhile goal, the objective may have been easier for Questlove to attain if Amy Winehouse had her way. Speaking with AP, Questlove confessed that the late songstress planned to build a supergroup consisting of him, Raphael Saadiq, and Mos Def. Winehouse’s shared love of music with Questlove opened the door for the pair to broaden their musical boundaries by exposing themselves to artists outside their preferred genres.


“She's such a jazz snob. I couldn't stand it, but I was obsessed with it because, once we exchanged information, she would always be on her computer sending me MP3s (like), ‘Listen to this.’ ... We spent a lot of time on Skype talking about crazy ideas and she schooled me about Sarah Vaughan. I schooled her about J Dilla," said Questlove, who noted what could have been possible if his friend were alive today.

“And she was like, 'All right, we're going to start a supergroup. You, me, Mos (Def), and Raphael Saadiq.' I was like, 'OK.' And she assigned homework: 'All right, study this record.' ... I really miss not having her here to school me on jazz; I thought I was a music snob, and I thought I had my doctorate in jazz, but no. There's so much more I could have learned. She's a teacher.”

Due to Winehouse's untimely death at age 27, the supergroup didn't become reality, but Questlove will still be among friends celebrating the music this summer at the upcoming "Roots Picnic." Tickets are available now for the fifth annual event, which will take place June 2-3 at the festival pier at Penn's Landing in Philadelphia, PA.

In addition to The Roots, performers will include Kid Cudi, De La Soul, Wale, Major Lazer, Diplo, St. Vincent, The Tune-Yards, Danny Brown, Shabazz Palaces, Moosh & Twist, Flosstradamus, Stretch Armstrong, The Hood Internet, Star Slinger, Mr. MFN Exquire, Kids These Days, Chill Moody, and DJ Diamond Kuts.