Christopher McCandless

Emile Hirsch

Jan Burres

Catherine Keener

Billie McCandless

Marcia Gay Harden

Walt McCandless

William Hurt

Ron Franz

Hal Holbrook

Carine McCandless

Jena Malone

Wayne Westerberger

Vince Vaughn

Rainey

Brian H. Dierker

Rainey

Brian Dierker

Tracy

Kristen Stewart

Kevin

Zach Galifianakis

Thomas

Thure Lindhardt

Gail Borah

Robin Mathews

Ted Turner

Kyle Kwon

Building Manager

Paul Knauls

Sonja

Signe Egholm Olsen

Bar Girl

Candice Campos

Himself

Jim Gallien

Lee's Ferry Ranger

Steven Wiig

Graduation Reader

James J. O'Neill

Waitress

Malinda McCollum

Chris McCandless - age 4

Bryce Walters

Bull

R.D. Call

Carine McCandless

Haley Ramm

Wayne's Crew #1

Craig Mutsch

Announcer

John Jabaley

Wayne's Crew #2

Jim Beidler

Emily Skeggs

Hutterite #1

John Decker

Francine Maisler

Hutterite #2

John Hofer

Additional Narration (voice)

Sharon Olds

Hutterite #3

Jerry Hofer

Himself

Leonard Knight

Hutterite #4

Terry Waldner

Man In Phone Booth

Floyd Wall

Immigration Officer

Jim Davis

Social Worker

Cheryl Francis Harrington

Lori

Merritt Wever

Insane Cain

Everett "Insane Wayne" Smith

Book Shopper #1

Matt Contreras

Book Shopper #2

Denise Sitton

Additional Narration (voice)

Carine McCandless

Director

Sean Penn

Director

Art Linson

Director

Bill Pohlad