4. Strained Relationship With Father
As a semi-successful doo-wop singer, Quest’s father, Lee Andrews, is in many ways his prime musical inspiration. But throughout his life, Quest has developed a deep-rooted strain in his relationship with his dad. He cites a time in middle school when he stole $25 dollars from his father in order to pay a friend back for breaking his boom box and, of course, to buy a couple cassettes. His father, a meticulous no-bullshit kinda guy, realized the money was missing immediately and gave young Questlove a “Kunta Kinte/Django Unchained–like whipping.” For Quest, this was a defining moment in his relationship with his father. And, as he mentions, an ironic one, as this beating came not just in the name of records, but in the name of The Jacksons Live! record.
And then, on a more personal level, when Quest’s mom moved out unannounced, his father didn’t know how to take it and became vulnerable and lost. Quest’s only reaction was to throw himself into work. He would escape reality by retreating to the studio. His relationship with his dad was the catalyst to his obsessive work routine and his subsequent life as an introvert.