Reese Witherspoon

Character: Cheryl Strayed

Laura Dern

Character: Bobbi Grey

Keene McRae

Character: Leif

Gaby Hoffmann

Character: Aimee

Michiel Huisman

Character: Jonathan

Kevin Rankin

Character: Greg

Cliff DeYoung

Character: Ed

Thomas Sadoski

Character: Paul

Randy Schulman

Character: Therapist

W. Earl Brown

Character: Frank

Brian Van Holt

Character: Ranger

Mo McRae

Character: Jimmy Carter

Will Cuddy

Character: Josh

Leigh Parker

Character: Rick

Nick Eversman

Character: Richie

Ray Buckley

Character: Joe

Cathryn de Prume

Character: Stacey

Kurt Conroyd

Character: Greg's Friend

Ted de Chatelet

Character: Greg's Friend

Jeffree Newman

Character: Greg's Friend

Lorraine Bahr

Character: Lou

Jerry Carlton

Character: Dave

Kevin-Michael Moore

Character: Spider

Debra Pralle

Character: Saleswoman

Gray Eubank

Character: Doctor

Anne Sorce

Character: Nurse

Charles Baker

Character: T.J.

J.D. Evermore

Character: Clint

Beth Hall

Character: Desk Clerk

Jan Hoag

Character: Annette

Carlee McManus

Character: Notary

Art Alexakis

Character: Tattooist

Anne Gee Byrd

Character: Vera

Jeanine Jackson

Character: Lecturer

Jason Newell

Character: Ronald Nylund

Barry O'Neil

Character: Young Suit #1

Richard Morris

Character: Young Suit #2

Bobbi Strayed Lindstrom

Character: Cheryl (6 Yrs Old)

Robert Alan Barnett

Character: Man at Gas Station

William Nelson

Character: Leif (3 Yrs Old)

Tony Doupe

Character: Man Behind Counter

Dan Considine

Character: Weird Dude

Andrew Saunderson

Character: Outdoor Store Clerk

Greg James

Character: Man at the Hotel Bar

Orianna Milne

Character: Paul's Girlfriend

Brian Borcherdt

Character: Grateful Dead Cover Band

Eric D. Johnson

Character: Grateful Dead Cover Band

Matt Pascua

Character: Wayne

Edric Carter

Character: Male Nurse

Matthew Noyes

Character: Grateful Dead Fan Musicians

John Dickerson Jr.

Character: Grateful Dead Fan Musicians

Denise McSweeny

Character: Toll Booth Operator

Alina Gatti

Character: College Freshman

Cheryl Strayed

Character: Woman in Truck

Evan O'Toole

Character: Kyle

Henry Shotwell

Character: Son of Man at Gas Station

Vincent M. Biscione

Character: Truck Driver (uncredited)

Dylan Hall

Character: Hippie Kid (uncredited)

Ted Rooney

Character: Crazy Guy (uncredited)