Matt Walsh Director, Screenwriter, Producer James Pumphery Fitz Actor Abby Elliott Monica Actor Dylan O'Brien Jimmy Actor Rob Riggle James Malone Sr. Actor Joe Lo Truglio Officer Fogerty Actor Lizzy Caplan Sheila Actor Matt L. Jones Richie Actor Zach Woods Tommy Actor Andrew Daly Mr. Doobin Actor Horatio Sanz Doctor Actor Kyle Gass Winter Wierdo Actor Brandon Johnson Cab Driver Actor Rich Fulcher Arnie Actor Seth Morris Berlin Bartender Actor Joseph A. Nunez Ramón Actor Josh Keaton Screenwriter Erik Rommesmo Executive Producer Jeff Schlossman Executive Producer Kirk Roos Producer Inman Young Producer Hillary Spera Cinematographer Alexis Hanawalt Film Editing Johnny Flanagan Production Design, Art Director Lauren Kolodny Costume Design