Stanley Tucci as Walter Winchell

Glenne Headly as Dallas Wayne

Paul Giamatti as Herman Klurfeld

Christopher Plummer as Franklin D. Roosevelt

Xander Berkeley as Gavreau

Kevin Tighe as William Randolph Hearst

Frank Medrano as Melvin Diamond

Vic Polizos as Sam Hague

John F. O'Donohue as Harry the Doorman

Michael Greene as Bellamy

Rod McCary as Emcee

Victoria Gabrielle Platt as Josephine Baker

Megan Mullally as June Winchell

Paul Mazursky as Winchell's Father

Francis X. McCarthy as Winchell's Attorney

Sven-Ole Thorsen as German Man

Mary Portser as Janet Winchell

Paul Jenkins as Lawrence Newman

Jason Huber as Ed Sullivan

Paula Cale as Mrs. Klurfeld

Don Fischer as Reporter #1

Kris Kamm as Reporter #2

Sean Michael Allen as Mirror Reporter (as Sean Barnes)

Joe Bays as Post Reporter #1

Joe Basile as Post Reporter #2

Michael Monks as Miami Reporter #1

Rick Scarry as Miami Reporter #2

Phillip Connery as Miami Reporter #3

David St. James as Miami Reporter #4

Robert Verlaque as Stork Club Reporter

Jon Menick as Precinct Reporter #2

Mason Lucero as Walter Jr. - Age 4

Ricky Davila as Walter Jr. - Age 10

Matt Bellner as Walter Jr. - Age 20

Sean Stavropoulos as Walter Winchell - Age 8

Raffi Di Blasio as Walter Winchell - Age 20

Danielle Beckstrom as Walda - Age 6

Kayley Gable as Walda - Age 12

Emily Saunders as Walda

Gary Donovan as Josephine Baker's Manager

Pat Asanti as Vaudeville Magician

Michael Laskin as Radio Executive #1

Lamont Johnson as Radio Executive #2

Sean Lawlor as Miami Sergeant

Richard Livingston as Musician

Jack Lotz as Bartender

Ray Lykins as Newman's Driver

Raf Mauro as Backstage Manager

Stuart Nisbet as Senator #1

J. Patrick McCormack as Senator #2

Clive Rosengren as Senator #3

Jack Shearer as Politician

Katherine Ann McGregor as Madam

Anthony Russell as Fitter

Enrique Peralta as Barber

Marshall Gitter as News Seller

Phillip Geoffrey Hough as Copy Boy

Joel Rooks as Stork Club Captain #1

Oliver Muirhead as Stork Club Captain #2

Stacey Brooks as Stork Club Patron #1

Tiffany Salerno as Stork Club Patron #2

Dennis Tracy as Stork Club Patron #3 (as Dennis A. Tracy)

Michael Chieffo as Photographer at Stork Club

Blayne Weaver as Country Club Worker

Palmer Davis as Showgirl

Peggy Miley as Candy Store Woman

James Wellington as First Doorman

Blake Rose as The Fighter

Carrie Stroud as Schwing Sister #1

Aria Rosenberg as Schwing Sister #2

Marissa Leigh as Schwing Sister #3 (as Marissa Leigh Baumgartner)

Tiffany Burton as Schwing Sister #4

Jonathan Aaron as Rabbi

Nina Savelle as Woman in Hotel Room

Tony Schubert as Cab Driver

Kate Brian as Girl with Walter

Carolyn Smith Bryant as Beautiful Woman

Joseph Benti as Announcer