100% CHANCE

Even after he postponed his scheduled tour, it’s been a heck of a busy year.

ALBUM

The Big Day, Bennett’s first full-length album, debuted at No. 2 on the Billboard 200 in July, making it his highest-charting release.

LIVE PERFORMANCE

In addition to a September show in Chicago, Bennett headlined London’s Lovebox Festival, the Life is Beautiful festival, and the iheartradio Music Festival.

COLLABORATIONS

Bennett’s vocals appeared on tracks by YBN Cordae, Supa Bwe, 2 Chainz, and Guapdad 4000.

SOUNDTRACK

Bennett produced and cowrote a song for September’s film version of Rebecca Sugar’s progressive animated series Steven Universe.

THE LION KING

Bennett surprised audiences with an unannounced cameo in Disney’s July remake.

RHYTHM AND FLOW

The Netflix talent competition show, which debuted in October, features Bennett as one of its celebrity judges.

BETWEEN TWO FERNS

Bennett made a cameo in the film, which came out in September.

DORITOS COMMERCIAL

Bennett starred with the Backstreet Boys in an ad that aired during the 2019 Super Bowl.

OPEN MIKE

Bennett oversees and often hosts this event, which invites Chicago high school students to perform music, poetry, and dance onstage.

WARMEST WINTER

This four-year-old effort collects donated winter clothing and distributes it to the homeless and transient population of Chicago.

SUPPORT CPS

Socialworks builds arts and literature programs in dozens of Chicago public schools. (Bennett has donated $1 million to the school system.)

KIDS OF THE KINGDOM

This Christian summer day camp was founded in 1978 by Bennett’s great-grandmother. (His 4-year-old daughter is a camper.)

MY STATE OF MIND

Bennett has personally given $1 million to the mental wellness fund, which pledged $600,000 to local service providers in 2018.

THE CHICAGOIST

Bennett bought the 15-year-old local news site in 2018 and is rebuilding it as an app that connects users to art, culture, and food in the city.