George Clooney as Miles

Catherine Zeta-Jones as Marilyn

Geoffrey Rush as Donovan Donaly

Cedric the Entertainer as Gus Petch

Edward Herrmann as Rex Rexroth

Paul Adelstein as Wrigley

Richard Jenkins as Freddy Bender

Billy Bob Thornton as Howard D. Doyle

Julia Duffy as Sarah Sorkin

Jonathan Hadary as Heinz, the Baron Krauss von Espy

Tom Aldredge as Herb Myerson

Stacey Travis as Bonnie Donaly

Jack Kyle as Ollie Olerud

Irwin Keyes as Wheezy Joe

Judith Drake as Mrs. Gutman

George Ives as Mrs. Gutman's Lawyer

Booth Colman as Gutman Trial Judge

Kristin Dattilo as Rex's Young Woman

Wendle Josepher as Miles' Receptionist

Mary Pat Gleason as Nero's Waitress

Mia Cottet as Ramona Barcelona

Kiersten Warren as Claire O'Mara

Rosey Brown as Gus's Pal

Ken Sagoes as Gus's Pal

Dale E. Turner as Gus's Pal

Douglas Fisher as Maitre d'

Nicholas Shaffer as Waiter

Isabell O'Connor as Judge Marva Munson

Mary Gillis as Court Reporter

Colin Linden as Father Scott

Julie Osburn as Stewardess

Gary Marshal as Las Vegas Waiter

Blake Clark as Convention Secretary

Allan Trautman as Convention Lawyer

Kate Luyben as Santa Fe Tart

Kitana Baker as Santa Fe Tart

Camille Anderson as Santa Fe Tart

Tamie Sheffield as Santa Fe Tart

Bridget Marquardt as Santa Fe Tart

Emma Harrison as Santa Fe Tart

John Bliss as Mr. MacKinnon

Patrick Thomas O'Brien as Bailiff

Sean Fenton as Bailiff

Bruce Campbell as Soap Opera Actor on TV (uncredited)