Winchell

Stanley Tucci

— Walter Winchell

Glenne Headly

— Dallas Wayne

Paul Giamatti

— Herman Klurfeld

Christopher Plummer

— Franklin D. Roosevelt

Xander Berkeley

— Gavreau

Kevin Tighe

— William Randolph Hearst

Frank Medrano

— Melvin Diamond

Vic Polizos

— Sam Hague

John F. O'Donohue

— Harry the Doorman

Michael Greene

— Bellamy

Rod McCary

— Emcee

Victoria Gabrielle Platt

— Josephine Baker

Megan Mullally

— June Winchell

Paul Mazursky

— Winchell's Father

Francis X. McCarthy

— Winchell's Attorney

Sven-Ole Thorsen

— German Man

Mary Portser

— Janet Winchell

Paul Jenkins

— Lawrence Newman

Jason Huber

— Ed Sullivan

Paula Cale

— Mrs. Klurfeld

Don Fischer

— Reporter #1

Kris Kamm

— Reporter #2

Sean Michael Allen

— Mirror Reporter (as Sean Barnes)

Joe Bays

— Post Reporter #1

Joe Basile

— Post Reporter #2

Michael Monks

— Miami Reporter #1

Rick Scarry

— Miami Reporter #2

Phillip Connery

— Miami Reporter #3

David St. James

— Miami Reporter #4

Robert Verlaque

— Stork Club Reporter