Alana Haim Alana Kane Cooper Hoffman Gary Valentine Sean Penn Jack Holden Tom Waits Rex Blau Bradley Cooper Jon Peters Benny Safdie Joel Wachs Skyler Gisondo Lance Brannigan Mary Elizabeth Ellis Momma Anita John Michael Higgins Jerry Frick Christine Ebersole Lucille Doolittle Harriet Sansom Harris Mary Grady Joseph Cross Matthew Danielle Haim Danielle Kane Este Haim Este Kane Maya Rudolph Gale Ryan Heffington Steve Nate Mann Brian Isabelle Kusman Sue Pomerantz Destry Allyn Spielberg Frisbee Kahill George DiCaprio Mr. Jack Iyana Halley Wig Shop Brenda Ray Chase B. Mitch Reed Emma Dumont Airplane Brenda Yumi Mizui Mioko Megumi Anjo Kimiko Emily Althaus Kiki Page Will Angarola Kirk Craig Stark Long Haired Freak Rogelio Camarillo Armand Ray Nicholson Ray Eloy Perez Guillermo James Kelley Tim Sasha Spielberg Tiny Toes Girl Anna Cordell Tiny Toes Girl Delaina Mitchell Stage Mom Liz Cackowski Stage Mom Tyler Young Audience Dad Erica Sullivan Director's Assistant Lakin Valdez Cop Allegra Clark Police Dispatch (voice) Ingrid Sophie Schram B. Mitch Reed Assistant Mary Eileen O'Donnell Reporter Jon Beavers Number 12 Creep Gerren Hall Campaign Employee (uncredited) Fatimah Hassan Driver (uncredited) Anthony Molinari Cop #2 (uncredited) John C. Reilly Fred Gwynne / Herman Munster (uncredited) Jeff Willy Fair Volunteer (uncredited)