When filmmaker Chris Wilcha revisits the record store he worked at as a teenager in New Jersey, he finds the once-thriving bastion of music and weirdness slowly falling apart and out of touch with the times. Flipside documents his tragicomic attempt to revive the store, while revisiting other documentary projects he has abandoned over the years. In the process, Wilcha captures This American Life icon Ira Glass in the midst of a creative rebirth, discovers the origin story of David Bowie’s ode to a local New Jersey cable television hero, and uncovers the unlikely connection between jazz photographer Herman Leonard and TV writer David Milch. This disparate collection of stories coheres into something strange and expansive—a moving meditation on music, work, and the sacrifices and satisfaction of trying to live a creative life.