Comedian-songwriter Henry Phillips (Henry Phillips) is lured to LA by renowned TV producer Jay Warren (J.K. Simmons), who hopes to create a television series about the life of a struggling performer. With the support of his longtime musician friend Jillian(Tig Notaro), and his well-meaning, but subpar, manager Ellen Pinsky(Ellen Ratner), Henry endures the ups and downs of LA; securing what appears to be the Hollywood dream. But when a major TV network gets involved with the show, Henry must decide whether his legacy will be to make jokes, or become the butt of them.