Reese Witherspoon
Cheryl Strayed
Kurt Conroyd
Greg's Friend
Ted de Chatelet
Greg's Friend
Jeffree Newman
Greg's Friend
Kevin-Michael Moore
Spider
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
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
Matthew Noyes
Grateful Dead Fan Musicians
John Dickerson Jr.
Grateful Dead Fan Musicians
Denise McSweeny
Toll Booth Operator
Alina Gatti
College Freshman
Cheryl Strayed
Woman in Truck
Henry Shotwell
Son of Man at Gas Station
Vincent M. Biscione
Truck Driver (uncredited)
Dylan Hall
Hippie Kid (uncredited)
Ted Rooney
Crazy Guy (uncredited)