Cheryl Strayed

Reese Witherspoon

Bobbi Grey

Laura Dern

Paul

Thomas Sadoski

Jonathan

Michiel Huisman

Leif

Keene McRae

Frank

W. Earl Brown

Aimee

Gaby Hoffmann

Greg

Kevin Rankin

Ed

Cliff DeYoung

Richie

Nick Eversman

Jimmy Carter

Mo McRae

Therapist

Randy Schulman

Ranger

Brian Van Holt

Josh

Will Cuddy

Rick

Leigh Parker

Joe

Ray Mist

Joe

Ray Buckley

Stacey

Cathryn de Prume

Greg's Friend

Kurt Conroyd

Greg's Friend

Ted DeChatelet

Greg's Friend

Ted de Chatelet

Greg's Friend

Jeffree Newman

Lou

Lorraine Bahr

Dave

Jerry Carlton

Spider

Kevin-Michael Moore

Saleswoman

Debra Pralle

Doctor

Gray Eubank

Nurse

Anne Sorce

T.J.

Charles Baker

Clint

J.D. Evermore

Desk Clerk

Beth Hall

Annette (Frank's Wife)

Jan Hoag

Notary

Carlee McManus

Tattooist

Art Alexakis

Vera

Anne Gee Byrd

Lecturer

Jeanine Jackson

Kyle

Evan O'Toole

Cheryl's Dad

Jason Newell

Young Suit #1

Barry O'Neil

Young Suit #1

Barry O'Neill

Young Suit #2

Richard Morris

Cheryl (6 Yrs Old)

Bobbi Strayed Lindstrom

Man At Gas Station

Robert Alan Barnett

Leif (3 Yrs Old)

William Nelson

Man Behind Counter

Tony Doupe

Weird Dude

Dan Considine

Outdoor Store Clerk

Andrew Saunderson

Man At The Hotel Bar

Greg James

Paul's Girlfriend

Orianna Milne

Grateful Dead Cover Band

Brian Borcherdt

Paul's Girlfriend

Orianna Herrman

Grateful Dead Cover Band

Eric D. Johnson

Wayne

Matt Pascua

Male Nurse

Edric Carter

Grateful Dead Fan Musicians

Matthew Noyes

Grateful Dead Fan Musicians

John Dickerson Jr.

Toll Booth Operator

Denise McSweeny

Grateful Dead Fan Musicians

John Dickerson

College Freshman

Alina Gatti

Woman in Truck

Cheryl Strayed

Son Of Man At Gas Station

Henry Shotwell

Truck Driver (uncredited)

Vincent M. Biscione

Hippie Kid (uncredited)

Dylan Hall

Crazy Guy (uncredited)

Ted Rooney