Bennett's father, Ken Bennett, has been involved in Democratic Party politics on the local and national level. Ken Bennett worked for Barack Obama as a presidential appointee and as an aide. Ken Bennett also worked on Obama's presidential campaign in 2008, and has worked as an aide to Mayor of Chicago Rahm Emanuel and as 2019 Chicago mayoral campaign co-chair for Toni Preckwinkle. Despite his family's ties to the Democratic Party, Bennett has called himself an independent voter, though he has a history of supporting Democrats. Bennett volunteered with Barack Obama's reelection campaign by phonebanking in Hyde Park, Chicago and has given speeches at the University of Chicago Institute of Politics.
In November 2014, Emanuel named Bennett as Chicago's Outstanding Youth of the Year for his activism. Bennett's work to support Chicago youth includes hosting Open Mike nights for Chicago-area high school students in collaboration with Chicago Public Library, which drew the attendance of fellow Chicago natives and celebrities like Hannibal Buress and Kanye West. In December 2015, Bennett joined with Detroit-based nonprofit group Empowerment Plan to start an initiative called Warmest Winter 2016. The initiative raised money to give 1,000 specially manufactured coats, which doubled as sleeping bags and shoulder bags, and were manufactured by homeless citizens of Detroit, to homeless citizens of Chicago. In June 2016, he hosted the Teens in the Park event, a free youth festival on Chicago's Northerly Island that drew an attendance of 3,300.
Bennett has actively fought to combat gun violence in his hometown of Chicago and in 2014, along with his father, promoted the "#SaveChicago" campaign. The campaign sought to stop gun violence over Memorial Day Weekend. During 2014's Memorial Day weekend, Chicago went 42 straight hours without a shooting. Bennett met with President Obama at the White House on April 16, 2016, to discuss My Brother's Keeper Challenge, an initiative of the United States Federal Government to promote intervention by civic leaders in the lives of young men of color to address their unique challenges and to promote racial justice, with other musicians, including Alicia Keys, Busta Rhymes, Janelle Monáe, J. Cole, and others. Bennett started a Twitter campaign for May 23, 2016 using #May23 to stop gun violence for 42 hours.
On March 6, 2017, after a meeting with Governor Bruce Rauner that did not go well only days before, Bennett announced his intention to donate $1,000,000 to Chicago Public Schools in order to help offset the lack of government funding provided. Following this, a movement arose to try and inspire Bennett to run for mayor of Chicago. This was backed by fellow media personalities including musician Drake.