Academy Award-nominated filmmaker Steve James’ fascinating and complex portrait of contemporary Chicago delivers a deep, multifaceted look into the soul of a quintessentially American city, set against the backdrop of its history-making 2019 mayoral election, and the tumultuous 2020 summer of COVID-19 and social upheaval following the police killing of George Floyd.

Dan Phillips is a 30-something bartender who lives and works in the ordinary city of Wessex. Dan's had the same friends since grade school, his most prized possession is a vintage Ms. Pac-Man game and his last serious relationship was with a girl who is now engaged to someone else. His life seems to be firmly on the path to more of the same... until a chance comment suddenly puts him in the running for mayor of Wessex.