Douglas McGrath
Alan Quimp

John Turturro
Crocker Johnson

Alan Cumming
General Batista

Sigourney Weaver
Daisy Quimp

Anthony LaPaglia
Fidel Castro

Jeffrey Jones
Senator Biggs

Paul Guilfoyle
Officer Hickle

Denis Leary
Officer Fry

Ryan Phillippe
Petrov

Terry Beaver
Mr. Judge

Sean Dugan
Skull and Bones Waiter

Grant Walden
Older Man

John Randolph Jones
Fobbs

Reathel Bean
Senator Farwood

Harriet Koppel
Stenographer

Kim Merrill
Woman in Line

Merwin Goldsmith
Mr. Brisk

Heather Matarazzo
Nora

Nathan Dean
Younger Man

Kathleen Chalfant
Mother Quimp

Larry Clark
Fred Quimp

Sandy McGrath
Tom Quimp

Frank Brosens
Chuck Quimp

Luis Placer
Man on the Beach

Noberto Kerner
Cuban Waiter

Jane Read Martin
Betty Crichton

Liz Welch Tirrell
Sally Smith

Octavio Gómez Berríos
Field Worker

Darlena Tejeiro
Rosa

Raul Aranas
Guard 1

José Ramón Rosario
Audience Member

Andrew Driscoll
The Lifeguards (Band Member)

Meredith Patterson
Marilyn Monroe

Bill Greenlee
The Lifeguards (Band Member)

David McKinley
The Lifeguards (Band Member)

Mateo Gómez
Aide

Matt Ross
Danny

John McDonnell
Emissary (Gorbachev)

Pablo Cunqueiro
Cuban Man

Tuck Milligan
President Kennedy

Susanna Hobrath
JFK's 3:30

Lisa Ganz
JFK's 3:30

Susan Stout
JFK's 3:30

Steven Banks
Officer Emmons

Brian Nelson
The Lifeguards (Band member)

Woody Allen
Lowther (uncredited)

Jason Antoon
Croupier (uncredited)