Despite his evasion of stylistic pigeonholing and no label affiliation -- not even a major-bankrolled vanity imprint -- Chance the Rapper became one of the most significant artists to infiltrate the mainstream during the 2010s. Through several mixtapes, his output underwent a rapid evolution as he celebrated life and faith, mourned personal loss, 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 a mixtape available only on streaming platforms, prompted headlines, yet they didn't overshadow the creative accomplishments that vaulted him onto the top tier.
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 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, Bennett'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, Bennett 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 Bennett 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, Bennett 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 Bennett, Coloring Book, arrived in May 2016. Enhanced by collaborators ranging from Ty Dolla $ign to Kirk Franklin, the album was well received by critics and listeners, and peaked at number eight on the Billboard 200. Bennett'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, Bennett 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. The year 2018 brought a handful of new solo singles, including "65th & Ingleside," "Work Out," and "I Might Need Security."