Back when music still mostly traveled by CD, Chancelor Bennett would get in trouble with his dad for handing out his mixtapes for free. You’ve gotta understand, his dad said, we worked for that money to buy those CDs. Now you’re giving them away. But the free thing wasn’t just about getting out there, Chance the Rapper explained to Apple Music in 2016. “It was kind of to throw out a beacon to let everybody see what could come of a free artist. I wanted people to associate those words—to see an independent artist’s independence.”

Bennett wasn’t the only artist figuring out how to ride the waves of the new musical economy, of course, but few have met the project with so much energy. Mixtapes, albums, whatever: The impression one gets of Chance isn’t just of a musician but a mission, a young man of faith documenting his passage into adulthood through a bright mix of hip-hop, gospel, and jazz, mixing exuberant spirituality with a grounded realness that makes him easy to cheer on.

Born in April 1993, Bennett grew up on the South Side of Chicago. His father was an aide to Barack Obama, while his mother worked for the Illinois Attorney General—a civic-mindedness Bennett carried into his own community and philanthropic work. His first mixtape, 10 Day, was recorded during a 10-day suspension from prep school for marijuana possession; his second, Acid Rap, dealt in part with postgrad self-exploration through LSD, conceits handled with a good-natured earnestness that made Bennett instantly relatable. After a star turn on Kanye West’s 2016 album The Life of Pablo, Bennett released Coloring Book, which went on to become the first streaming-only album to reach the Billboard 200 and, subsequently, to win a Grammy. (“He said let’s do a good-ass job with Chance three/I hear you gotta sell it to snatch the Grammy,” Bennett rapped on Pablo’s “Ultralight Beam.” “Let's make it so free and the bars so hard that there ain’t one gosh-darn part you can’t tweet.”)

Chance's first studio album, The Big Day, came out in mid-2019. His activism has included the co-creation of a nonprofit designed to create programs for Chicago youth, participating in campaigns to combat the city’s gun violence, and speaking out in general in advocacy of government intervention and support in the lives of young black men. In early 2017, he donated $1,000,000 to Chicago Public Schools; later the same year, he donated another $2.2 million through nonprofit fundraising. In between, he got a public thanks at the city’s annual Bud Billiken Parade from Barack Obama, a fan.