Reese Witherspoon
Cheryl Strayed
Laura Dern
Bobbi Grey
Keene McRae
Leif
Gaby Hoffmann
Aimee
Michiel Huisman
Jonathan
Kevin Rankin
Greg
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
Ray Buckley
Joe
Cathryn de Prume
Stacey
Kurt Conroyd
Greg's Friend
Ted de Chatelet
Greg's Friend
Jeffree Newman
Greg's Friend
Lorraine Bahr
Lou
Jerry Carlton
Dave
Kevin-Michael Moore
Spider
Debra Pralle
Saleswoman
Gray Eubank
Doctor
Anne Sorce
Nurse
Charles Baker
T.J.
J.D. Evermore
Clint
Beth Hall
Desk Clerk
Jan Hoag
Annette
Carlee McManus
Notary
Art Alexakis
Tattooist
Anne Gee Byrd
Vera
Jeanine Jackson
Lecturer
Jason Newell
Ronald Nylund
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
William Nelson
Leif (3 Yrs Old)
Tony Doupe
Man Behind Counter
Dan Considine
Weird Dude
Andrew Saunderson
Outdoor Store Clerk
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
Edric Carter
Male Nurse
Matthew Noyes
Grateful Dead Fan Musicians
John Dickerson
Grateful Dead Fan Musicians
Denise McSweeny
Toll Booth Operator
Alina Gatti
College Freshman
Cheryl Strayed
Woman in Truck
Evan O'Toole
Kyle
Henry Shotwell
Son of Man at Gas Station
Vincent M. Biscione
Truck Driver (uncredited)
Dylan Hall
Hippie Kid (uncredited)
Ted Rooney
Crazy Guy (uncredited)