Bill Hader Milo Dean Kristen Wiig Maggie Dean Luke Wilson Lance Ty Burrell Rich Levitt Boyd Holbrook Billy Joanna Gleason Judy Kathleen Rose Perkins Carlie Van der Hoff Adriane Lenox Dr. Linda Essex Eddie Schweighardt Young Milo Dean Paul Castro Jr. Eric Levitt Benjamin McGowan Cullen Genevieve Adams Store Manager Truck Hudson Security Officer Cliff Moylan Police Officer Ian Hyland Waiter (uncredited) David Garelik College Dude (uncredited) Jennifer Lafleur Drunk Natalie (uncredited)