The Heyday of the Insensitive Bastards

James Franco

Conrad

Natalie Portman

Laura

Kristen Wiig

Monica

Kate Mara

Lisa

Amber Tamblyn

Amanda

Jim Parrack

Paul

Abigail Spencer

Abigail

Keir Gilchrist

Michael

Thomas Mann

Lee

Rico Rodriguez

Charlie Foster

Matthew Modine

Theodore Foster

Jimmy Kimmel

Mr. Chipmunk

Tony Cox

Mr. Chubb

Bo Mitchell

Greg

Jacob Loeb

Keen

Kelsey Ledgin

Lila

Tyler Labine

Clete

Jack Kehler

Sheriff Mallon

Wendy Phillips

Mrs. Nighetti

Frank Birney

Edmund

Muriel Minot

Caddy

Priscilla Garita

Maricelle Foster

Tanner Buchanan

Bobby Bell

Wilmer Calderon

Barnett

Kai Lennox

Timmy

Ella Anderson

Sally

Charlie Martin

Cliff

David May

Brian

Katie Cofield

Val

June Conniff

Ophelia

Tom Paliferro

Sydney

Robert DuBois

Stu

Adam J. Harrington

Henry

Milan Johnson

Zach Cuttle

Alex Oberheide

Preston

Bryan Patrick West

Skins

Malia Pyles

Amber

Pappy Faulkner

Jimmy

Isaac Faulkner

Nate

Max Leifman

Young Conrad

Rebecca Ellen Evans

Young Lisa

Lili Brennan

Young Amanda

Jack Sochet

Conrad's Father

Toni Gaal

Greg's Mom

Bridget Bowes

Brian's Wife

Maite Pistiner

Michael’s Love Interest

Brian Lally

Therapist

Anthony Sherritt

Swinger

Maya Zapata

Babysitter