Chancelor Jonathan Bennett was born in Chicago, Illinois to Ken Williams-Bennett, an aide to former Chicago mayor Harold Washington and then-Senator Barack Obama, and Lisa Bennett, a secretary for the office of Illinois Attorney General. Bennett grew up in the middle-class neighborhood of West Chatham on Chicago’s South Side. When Bennett was thirteen, his father began to work for President Barack Obama during his first term in the Department of Labor. Bennett personally met President Obama in his youth and discussed his aspirations to be a rapper, to which Obama responded with “word”. Bennett was originally going to move to Washington, D.C. following Obama’s win in the 2008 presidential election though those plans eventually fell through. Bennett attended Jones College Prep High School where he was a member of the Jewish Student Union. During his time in high school, Bennett did not get good grades and was suspended often.
Bennett’s interest in music began with Michael Jackson, who he exclusively listened to on cassettes until the fifth grade. Growing up, Bennett’s parents were constantly playing music, including Billie Holiday and Sam Cooke and other artists in the jazz and gospel genres. Bennett began listening to hip-hop after hearing “Through the Wire” by Kanye West on the radio whilst walking through Hyde Park, Chicago. 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 considers West a huge influence on him and has said that he was inspired to begin rapping by West. Bennett and West met each other in August 2014 at Bonnaroo Music Festival.