Adam Sandler as Charlie Fineman

Don Cheadle as Alan Johnson

Jada Pinkett Smith as Janeane Johnson

Liv Tyler as Angela Oakhurst

Saffron Burrows as Donna Remar

Donald Sutherland as Richter Raines

Robert Klein as Jonathan Timpleman

Melinda Dillon as Ginger Timpleman

Mike Binder as Bryan Sugarman

Jonathan Banks as Stelter

Rae Allen as Adell Modell

Paula Newsome as Melanie

John de Lancie as Nigel Pennington

Paul Butler as George Johnson

Camille LaChe Smith as Cherie Johnson

Imani Hakim as Jocelyn Johnson

Denise Dowse as Psychiatric Hospital Therapist

Anthony Chisholm as William Johnson

B.J. Novak as Mr. Fallon

Jessica Golden as Night Club Comic

Ted Raimi as Peter Savarino

Harris Peet as Kemp

Molly Binder as Becky Fishman

Tommy Nohilly as Patty

Robert Harvey as Dental Partner

Nick Taylor as Taxi Driver

M.D. Walton as New York Police Officer #1

Chad Brigockas as New York Police Officer #2

Elizabeth Andrews as Sugarman's Secretary

Neal Young as New Dental Patient

Lela Loren as Dental Hygienist

Joey King as Gina Fineman (uncredited)

Gina Fricchione as Dr. Johnson's Waiting Room Patient (uncredited)

Diana Gettinger as Doreen Fineman (uncredited)

Karen Huie as News Reporter (uncredited)

Lou Irizarry as Moving Man (uncredited)

Andre M. Johnson as New York Police Officer (uncredited)

Arick Salmea as Rock Club Guy (uncredited)

Nick Vlassopoulos as Examining Doctor (uncredited)