Clea Duvall Jessie Director, Actor, Screenwriter, Executive Producer Melanie Lynskey Annie Actor Natasha Lyonne Sarah Actor Vincent Piazza Peter Actor Jason Ritter Matt Actor Ben Schwartz Jack Actor Alia Shawkat Lola Actor Cobie Smulders Ruby Actor Sam Slater Producer Paul Bernon Producer Sev Ohanian Producer Mel Eslyn Executive Producer David Bernon Executive Producer Polly Morgan Cinematographer Tamara Meem Film Editing Sara Quinn Original Music Lanie Faith Marie Overton Production Design Alex Simone Costume Design Amey Rene Morris Casting