Conrad

James Franco

Lisa

Kate Mara

Laura

Natalie Portman

Moniica

Kristen Wiig

Charlie Foster

Rico Rodriguez

Abigail

Abigail Spencer

Amanda

Amber Tamblyn

Paul

Jim Parrack

Theodore Foster

Matthew Modine

Lee

Thomas Mann

Michael

Keir Gilchrist

Mr. Chubb

Tony Cox

Mr. Chipmunk

Jimmy Kimmel

Keen

Jacob Loeb

Greg

Bo Mitchell

Helen

Ahna O'Reilly

Lila

Kelsey Ledgin

Clete

Tyler Labine

Lila

Kelsey Ford

Sheriff Mallon

Jack Kehler

Bobby Bell

Tanner Buchanan

Henry

Adam Harrington

Mrs. Nighetti

Wendy Phillips

Edmund

Frank Birney

Caddy

Muriel Minot

Maricelle Foster

Priscilla Garita

Barnett

Wilmer Calderon

Timmy

Kai Lennox

Sally

Ella Anderson

Cliff

Charlie Martin

Brian

David May

Val

Katie Cofield

Ophelia

June Conniff

Sydney

Tom Paliferro

Stu

Robert DuBois

Henry

Adam J. Harrington

Zach Cuttle

Milan Johnson

Preston

Alex Oberheide

Skins

Bryan Patrick West

Amber

Malia Pyles

Jimmy

Pappy Faulkner

Nate

Isaac Faulkner

Young Conrad

Max Leifman

Young Lisa

Rebecca Ellen Evans

Young Amanda

Lili Brennan

Conrad's Father

Jack Sochet

Greg's Mom

Toni Gaal

Brian's Wife

Bridget Bowes

Michael’s Love Interest

Maite Pistiner

Therapist

Brian Lally

Swinger

Anthony Sherritt

Babysitter

Maya Zapata