Suggestions by @ben_quigels
272 suggestions
Frank Sinatra
as John Laurens in Hamilton in Old Hollywood
Rita Moreno
as Maria Reynolds in Hamilton in Old Hollywood
Donald O'Connor
as Philip Hamilton in Hamilton in Old Hollywood
Margaret O'Brien
as Margarita Schuyler in Hamilton in Old Hollywood
Dick Van Dyke
as King George III in Hamilton in Old Hollywood
Judy Garland
as Angelica Schuyler in Hamilton in Old Hollywood
Ray Charles
as Gilbert du Motier in Hamilton in Old Hollywood
Gordon MacRae
as George Washington in Hamilton in Old Hollywood
Julie Andrews
as Elizabeth Hamilton in Hamilton in Old Hollywood
John Ford
as Director in Star Wars as Classic Hollywood (1950s)
Jean Simmons
as Leia Organa in Star Wars as Classic Hollywood (1950s)
Shirley Temple
as Little Red Riding Hood in Into the Woods (Old Hollywood)
Bobby Driscoll
as Jack in Into the Woods (Old Hollywood)
Katharine Hepburn
as The Giantess in Into the Woods (Old Hollywood)
Donald Meek
as Cinderella's Father in Into the Woods (Old Hollywood)
Doris Day
as Cinderella's Mother in Into the Woods (Old Hollywood)
David Tomlinson
as The Steward in Into the Woods (Old Hollywood)
Frank Sinatra
as The Big Bad Wolf in Into the Woods (Old Hollywood)
Judith Anderson
as Cinderella's Stepmother in Into the Woods (Old Hollywood)
Judy Holliday
as Lucinda in Into the Woods (Old Hollywood)