Warren Beatty as Mike Gambril

Annette Bening as Terry McKay

Katharine Hepburn as Ginny

Garry Shandling as Kip DeMay

Chloe Webb as Tina Wilson

Pierce Brosnan as Ken Allen

Kate Capshaw as Lynn Weaver

Paul Mazursky as Herb Stillman

Brenda Vaccaro as Nora Stillman

Glenn Shadix as Anthony Rotundo

Barry Miller as Robert Crosley

Harold Ramis as Sheldon Blumenthal

Linda Wallem as Lorraine

Meagen Fay as SSA Flight Attendant

Ray Girardin as Wally Tripp

John Hostetter as Ben

Elya Baskin as Ship Captain

Boris Lee Krutonog as Second Officer

Savely Kramarov as Cable Officer

Oleg Vidov as Russian Businessman

Taylor Dayne as Marissa

Carey Lowell as Martha

Ed McMahon as Self

Dan Castellaneta as Phil

Jeffrey Nordling as Lou

Rosalind Chao as Lee

Rebecca Miller as Receptionist

Tom Signorelli as Cab Driver

Cylk Cozart as Dr. Punch

Robert Levine as Dr. Kaplan

Frank Campanella as Elevator Operator

Wendie Jo Sperber as Helen

McNally Sagal as TV Reporter

Gary McGurk as Waiter

Helena Carroll as Dorothy

Manu Tupou as Rau

Irene Olga López as Annie

Lisa Edelstein as Assistant at Studio

Stefan Lysenko as Russian Sailor

Marek Probosz as Russian Sailor

Sergey Brusilovsky as Russian Waiter

Herman Sinitzyn as Russian Waiter

Rosalind Allen as Qantas Flight Attendant

James Pyduck as Bell Captain

Jack Johnson as Matthew Stillman

Lori Sebourn-Carhart as Blonde Woman

Michael Gordon Bennett as Lynn's Chauffeur

Michael Fischetti as Street Man

Michael F. Boyle as Bellman

Mary Hart as Self

John Tesh as Self

Steve Kmetko as Self

Terry Murphy as Self

Barry Nolan as Self

Andrea Kutyas as Self

Ray Charles as Self

James W. Lively as Single and Jingle Children

Laurie A. Schillinger as Single and Jingle Children

Jessica Rotter as Sing and Jingle Children