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

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 Jr.

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)