Jeffrey Goines
Mickey O'Neil
Rusty Ryan
Paul Maclean
Joe Black
Floyd (Dick's Roommate)
Heinrich Harrer
Richard Jones
Tyler Durden
Louis
Tom Bishop
J.D.
Achilles
John Smith
Mills
Michael Sullivan
Pam's Man
Early Grayce
Billy Canton
Tristan Ludlow
Francis Austin McGuire / Rory Devaney
Jesse James
Benjamin Button
Chad Feldheimer
Dwight Ingalls
Self
Jerry Welbach
Mr. O'Brien
Rick
Sinbad (voice)
Detective Frank Harris
Sonny Hayes
Billy Beane
Metro Man (voice)
Johnny Suede
Partygoer / Preppie Kid at Fight (uncredited)
Jackie Cogan
LT. Aldo Raine
Will (voice)
Joe Maloney
Elliott Fowler
Gerry Lane
Brian
Steve Black
Samuel Bass
Self (archive footage)
(archive footage)
Westray
Don 'Wardaddy' Collier
Cox
Narrator (voice)
Bachelor Brad
Roland
Ben Rickert
Boy at the Beach (uncredited)
Brad Pitt / Self
Gen. Glen McMahon
Jack Conrad
Brad Pitt
Billy (segment "King of the Road")
The Madman
Sinbad
Max Vatan
Teddy Johnson
Judge Vaughn Walker
Waiter (uncredited)
Brad Pitt (uncredited)
Cliff Booth
Vanisher
Sgt. Bill Mauldin
Party Guest
Roy McBride
Ladybug
Self (Archival Footage)
Jack Trainer
Video footage
Jeff
Bernard
Peter
Will Colbert (uncredited)
Patch Boomhauer (voice)
Billy
Self - Judge
Self - Guest
Randy
Walker Lovejoy
Jonathan Keith
Jim Jefferies Show Weatherman
Ex-Weatherman
Self - Cameo (uncredited)
Weatherman
Self - Nominee