- Reese Witherspoon
- Cheryl
- Laura Dern
- Bobbi
- Thomas Sadoski
- Paul
- Keene McRae
- Leif
- Michiel Huisman
- Jonathan
- W. Earl Brown
- Frank
- Gaby Hoffmann
- Aimee
- Kevin Rankin
- Greg
- Brian Van Holt
- Ranger
- Cliff De Young
- Ed
- Mo McRae
- Jimmy Carter
- Will Cuddy
- Josh
- Leigh Parker
- Rick
- Nick Eversman
- Richie
- Ray Buckley
- Joe
- Randy Sean Schulman
- Therapist
- Cathryn de Prume
- Stacey
- Kurt Conroyd
- Greg's Friend
- Ted deChatelet
- 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.
- JD Evermore
- Clint
- Beth Hall
- Desk Clerk
- Jan Hoag
- Annette (Frank's Wife)
- Carlee McManus
- Notary
- Art Alexakis
- Tattooist
- Anne Gee Byrd
- Vera
- Evan O'Toole
- Kyle
- Jeanine Jackson
- Lecturer
- Jason Newell
- Cheryl's Dad
- Barry O'Neil
- Young Suit #1
- Rich 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 Musician
- John Dickerson Jr.
- Grateful Dead Fan Musician
- Denise McSweeny
- Toll Booth Operator
- Alina Gatti
- College Freshman
- Henry Shotwell
- Son of Man at Gas Station
- Cheryl Strayed
- Woman in Truck
- Zackry Ayres
- Dead Head / Extra (uncredited)
- Joseph Thomas Bailey
- Native American Man Crossing the Road w / Fishing Equipment (uncredited)
- Sara Bailey
- Mother of Two at the Gas Station
- Brett Barron
- Drunk Guy #2
- Vincent M. Biscione
- Truck Driver
- Richard G. Boron
- St. Patrick
- Cody Burns
- Restaurant Patron
- Miles Cardin
- College Student
- William "Will" Daubert
- Gas Station Attendent
- Matthew Joel Flood
- Grateful Dead Hippie - Matthew
- Elizabeth Fournier
- Hippie Chick
- Bekah Grace
- Ashland Local / Deadhead (uncredited)
- Dylan Hall
- Hippie Kid
- Simos Kalivas
- Deadhead Bartender
- Brent Kublick
- Drunk Guy #1
- Dylan Wayne Lawrence
- Frat Guy
- Jacob Looper
- College Student
- Jamie McCall
- St Patrick's Day Patron
- Edwin Modlin II
- Hot Smoking Guy
- Brett Nemecek
- Bar Patron
- Blaine Palmer
- Store Assistant
- Jennifer Penner
- St Patrick's Day Patron
- Elizabeth Pennington
- College Student
- Ted Rooney
- Crazy Guy
- Trip Ross
- Punk
- Eric Sahlstrom
- Hospital Visitor
- Peter Simpson
- Man in Bar
- Jamie Martin Stewart
- Hippie DJ
- Wayne Sweat
- Tourist
- Robert Zorn
- Homeless Man with Dog
