Michael Douglas as Grady Tripp

Tobey Maguire as James Leer

Frances McDormand as Sara Gaskell

Robert Downey Jr. as Terry Crabtree

Katie Holmes as Hannah Green

Rip Torn as Q

Richard Knox as Vernon Hardapple

Jane Adams as Oola

Michael Cavadias as Miss Sloviak

Richard Thomas as Walter Gaskell

Alan Tudyk as Sam Traxler

Philip Bosco as Emily's Father

George Grizzard as Fred Leer

Kelly Bishop as Amanda Leer

Bill Velin as Officer Pupcik

Charis Michelsen as Carrie

Yusuf Gatewood as Howard

June Hildreth as Emily's Mother

Elisabeth Granli as Emily (photo)

Richard Hidlebird as Hi-Hat Bouncer

Screamer as Poe

Bingo O'Malley as Wordfest Party Guest

Patricia Cray as Wordfest Party Guest

Marita Golden as Wordfest Party Guest

Victor Quinaz as Wordfest Party Guest

James Ellroy as Wordfest Party Guest

Lenora Nemetz as Wordfest Party Guest

Tracey D. Turner as Wordfest Party Guest

James Kisicki as Wordfest Party Guest

Rob McElhenney as Student

Anika Bobb as Student

Katherine Sweeney as Student

Katrina M. Faessel as Student (uncredited)

John W. Iwanonkiw as Father at Hospital (uncredited)

Sean King as Student (uncredited)

David Lean as Student (uncredited)

Jackson Nunn as Night Club Dancer (uncredited)

Sandy Slicker as Woman in Forum (uncredited)

Andrew Zehner as Student (uncredited)