Reese Witherspoon
Cheryl Strayed

Laura Dern
Bobbi Grey

Keene McRae
Leif

Gaby Hoffmann
Aimee

Michiel Huisman
Jonathan

Kevin Rankin
Greg

Cliff DeYoung
Ed

Thomas Sadoski
Paul

Randy Schulman
Therapist

W. Earl Brown
Frank

Brian Van Holt
Ranger

Mo McRae
Jimmy Carter

Will Cuddy
Josh

Leigh Parker
Rick

Nick Eversman
Richie

Cathryn de Prume
Stacey

Kurt Conroyd
Greg's Friend

Ted de Chatelet
Greg's Friend

Lorraine Bahr
Lou

Debra Pralle
Saleswoman

Gray Eubank
Doctor

Charles Baker
T.J.

J.D. Evermore
Clint

Beth Hall
Desk Clerk

Jan Hoag
Annette

Art Alexakis
Tattooist

Anne Gee Byrd
Vera

Jeanine Jackson
Lecturer

Barry O'Neil
Young Suit #1

Richard Morris
Young Suit #2

Bobbi Strayed Lindstrom
Cheryl (6 Yrs Old)

Robert Alan Barnett
Man at Gas Station

Tony Doupe
Man Behind Counter

Dan Considine
Weird Dude

Greg James
Man at the Hotel Bar

Orianna Milne
Paul's Girlfriend

Brian Borcherdt
Grateful Dead Cover Band

Eric D. Johnson
Grateful Dead Cover Band

Matt Pascua
Wayne

Cheryl Strayed
Woman in Truck

Evan O'Toole
Kyle

Dylan Hall
Hippie Kid (uncredited)

Ted Rooney
Crazy Guy (uncredited)