Bennett and West met each other in August 2014 at Bonnaroo Music Festival. Bennett considers West a huge influence on him and has said that he was inspired to begin rapping by West. After finding out the song was on West's debut album The College Dropout, Bennett purchased the album, making it the first hip-hop album that Bennett listened to. Bennett began listening to hip-hop after hearing " Through the Wire" by Kanye West on the radio while walking through Hyde Park, Chicago. Growing up, Bennett's parents were constantly playing music, including Billie Holiday, Sam Cooke and other artists in the jazz and gospel genres. īennett's interest in music began with Michael Jackson, who he exclusively listened to on cassettes until the fifth grade. Bennett attended Jones College Prep High School where he was a member of the Jewish Student Union. following Obama's win in the 2008 presidential election, though those plans eventually fell through. Bennett was originally going to move to Washington, D.C. Bennett personally met President Obama in his youth and discussed his aspirations to be a rapper, to which Obama responded with "word". When Bennett was sixteen, his father began to work in the Department of Labor during President Barack Obama's first term. Bennett grew up in the middle-class neighborhood of West Chatham on Chicago's South Side. His mother, Lisa Bennett, worked for the Illinois Attorney General.
His father, Ken Williams-Bennett, was an aide to the late Chicago mayor Harold Washington and then-Senator Barack Obama.