The Heyday of the Insensitive Bastards

James Franco

Conrad

Age 36 (now 48)

Natalie Portman

Laura

Age 33 (now 44)

Kristen Wiig

Monica

Age 41 (now 52)

Kate Mara

Lisa

Age 32 (now 43)

Amber Tamblyn

Amanda

Age 31 (now 43)

Jim Parrack

Paul

Age 34 (now 45)

Abigail Spencer

Abigail

Age 33 (now 44)

Keir Gilchrist

Michael

Age 22 (now 33)

Thomas Mann

Lee

Age 23 (now 34)

Rico Rodriguez

Charlie Foster

Age 16 (now 27)

Matthew Modine

Theodore Foster

Age 56 (now 67)

Jimmy Kimmel

Mr. Chipmunk

Age 47 (now 58)

Tony Cox

Mr. Chubb

Age 56 (now 68)

Bo Mitchell

Greg

Age 20 (now 31)

Jacob Loeb

Keen

Kelsey Ledgin

Lila

Tyler Labine

Clete

Age 36 (now 48)

Jack Kehler

Sheriff Mallon

Age 68 (died at 75)

Wendy Phillips

Mrs. Nighetti

Age 63 (now 74)

Frank Birney

Edmund

Age 77 (died at 83)

Muriel Minot

Caddy

Priscilla Garita

Maricelle Foster

Age 46 (now 58)

Tanner Buchanan

Bobby Bell

Age 16 (now 27)

Wilmer Calderon

Barnett

Age 39 (now 51)

Kai Lennox

Timmy

Age 41 (now 52)

Ella Anderson

Sally

Age 9 (now 21)

Charlie Martin

Cliff

David May

Brian

Katie Cofield

Val

June Conniff

Ophelia

Tom Paliferro

Sydney

Robert DuBois

Stu

Adam J. Harrington

Henry

Age 42 (now 53)

Milan Johnson

Zach Cuttle

Alex Oberheide

Preston

Bryan Patrick West

Skins

Malia Pyles

Amber

Age 14 (now 25)

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

Age 50 (now 61)

Anthony Sherritt

Swinger

Maya Zapata

Babysitter

Age 33 (now 44)