Jon Hamm as Sid Luft (voice)

Jennifer Jason Leigh as Judy Garland (voice)

Judy Garland as Self (archive footage)

Fred Astaire as Self (archive footage)

Count Basie as Self (archive footage)

George Cukor as Self (archive footage)

Mary Jane Gumm as Self (archive footage)

Virginia Gumm as Self (archive footage)

Lena Horne as Self (archive footage)

George Jessel as Self (archive footage)

Norman Jewison as Self (voice)

Gene Kelly as Self (archive footage)

Joey Luft as Self (archive footage)

Lorna Luft as Self (archive footage)

Dean Martin as Self (archive footage)

James Mason as Self (archive footage)

Liza Minnelli as Self (archive footage)

Jack Paar as Self (archive footage)

Martha Raye as Self (archive footage)

Mickey Rooney as Self (archive footage)

George Schlatter as Self (voice)

Frank Sinatra as Self (archive footage)

Barbra Streisand as Self (archive footage)

Jerry Van Dyke as Self (archive footage)

Louis B. Mayer as Self (archive photos)

John F. Kennedy as Self (archive photos)

Jack L. Warner as Self (archive photos)

Peter Lawford as Self (archive photos)

Grace Kelly as Self (archive footage/photos)

Ronald Reagan as Self (archive footage)

Freddie Fields as Self (archive photos and voice)

Miss Major Griffin-Gracy as Self (archive voice)

Andre Phillipe as Self (archive voice)