Despite his evasion of stylistic pigeonholing and no label affiliation -- not even a major-bankrolled vanity imprint -- Chance the Rapper is one of the most significant independent artists to infiltrate the mainstream. Through several mixtapes, his output underwent a rapid evolution as he celebrated life and faith, mourned personal losses, and hit upon lighter everyday experiences with high-aptitude wordplay served with a variety of mostly genial styles. All the while, the productions that supported the verses and hooks included various regional contemporary rap production styles, and among other genres synthesized elements of gospel, jazz, and soul. Previously unthinkable achievements, such as winning a Grammy Award for Best Rap Album with 2016's Coloring Book -- a mixtape available only on streaming platforms -- prompted headlines, yet they didn't overshadow the creative accomplishments that vaulted him onto the top tier. Chance continued to evolve with the delivery of his long-awaited debut studio album, 2019's The Big Day. He has stayed busy, collaborating on tracks with Ludacris, Justin Bieber, Vic Mensa, and others.

A native of Chicago's West Chatham neighborhood, Chancelor Bennett made his mixtape debut in April 2012 with 10 Day, a wide-ranging effort recorded during -- and partly inspired by -- a high-school suspension of the same duration. Featuring beats from Flying Lotus, Chuck Inglish, and Lex Luger, it was preceded by advance notice from Complex and followed by praise from Forbes. One of Bennett's early supporters was Childish Gambino, who took him on as opener for a U.S. tour. Increasing popularity didn't prevent Bennett from visiting local schools, deepening a lasting humanitarian connection with his community. Second tape Acid Rap, Chance's first release to register on Billboard's album charts, arrived in April 2013 and intensified efforts from major labels who wanted to sign the artist, only to be turned down. By the end of that year, he had strengthened his commercial appeal with an appearance on Justin Bieber's "Confident," a single that nearly reached the Top 40 on its way to a gold RIAA certification. Months later, XXL magazine selected Chance for their 2014 Freshman list, a group that included fellow Chicagoans Vic Mensa and Lil Durk.

From 2014 through the first four months of 2016, Chance was heard primarily on collaborations with artists who included Madonna ("Iconic"), Action Bronson ("Baby Blue"), Snakehips ("All My Friends"), and Kanye West ("Ultralight Beam"). There was also extensive involvement in Surf, an album from Donnie Trumpet the Social Experiment, and Free, a six-track mixtape co-billed with Lil B. The next proper release from Chance, Coloring Book, arrived in May 2016. Enhanced by collaborators ranging from Ty Dolla $ign to Kirk Franklin, the full-length was well received by critics and listeners, and peaked at number eight on the Billboard 200. Chance's 2016 output as a headliner and featured artist led to seven Grammy nominations. He took the award for Best New Artist, Coloring Book won Best Rap Album, and Best Rap Performance went to him, Lil Wayne, and 2 Chainz for "No Problem."

During the first half of 2017, Chance lengthened his discography of featured appearances through tracks by brother Taylor Bennett and Brian Fresco, as well as DJ Khaled, whose "I'm the One" topped the Billboard Hot 100. In July 2018, Chance simultaneously released four singles, including "I Might Need Security," and appeared on another Khaled hit, "No Brainer," which quickly went Top Ten pop. The non-album single "Groceries" arrived in 2019, along with guest spots on tracks by Ed Sheeran and Cordae.

In July 2019, Chance's long-promised and highly anticipated debut studio album, The Big Day, finally arrived. Based loosely on a wedding day theme and heavy on lyrics about family and maturation, the record boasted a long list of prestigious contributors as wide-ranging as Nicki Minaj, Death Cab for Cutie, Randy Newman, CocoRosie, and actor John Witherspoon. The Big Day debuted in the number two position on the Billboard charts. In 2020, Chance issued several singles of his own, including the Ludacris collaboration "Found You," and he featured on tracks by Justin Bieber and MadeinTYO. More non-album tracks arrived with 2022's "Wraith," featuring Vic Mensa and Smoko Ono, and "The Highs & the Lows," featuring Joey Bada$$. ~ Andy Kellman, Rovi