Suggestions by @ben_quigels

Margaret O'Brien

as Sansa Stark in Game of Thrones as Classic Hollywood

Score: +1

Howard Keel

as Eddard Stark in Game of Thrones as Classic Hollywood

Score: +1

Cary Grant

as Petyr Baelish in Game of Thrones as Classic Hollywood

Score: +1

Billy Barty

as Tyrion Lannister in Game of Thrones as Classic Hollywood

Score: +1

James Dean

as Rob Stark in Game of Thrones as Classic Hollywood

Score: 0

Clark Gable

as Jaime Lannister in Game of Thrones as Classic Hollywood

Score: +1

Barbara Stanwyck

as Cersei Lannister in Game of Thrones as Classic Hollywood

Score: +1

King Fergus

as Robert Baratheon in Game of Thrones (Disney characters)

Score: +1

Laurence Olivier

as Aaron Burr in Hamilton in Old Hollywood

Score: +1

Rod Steiger

as Hercules Mulligan in Hamilton in Old Hollywood

Score: +1

Frank Sinatra

as John Laurens in Hamilton in Old Hollywood

Score: +1

Rita Moreno

as Maria Reynolds in Hamilton in Old Hollywood

Score: +1

Donald O'Connor

as Philip Hamilton in Hamilton in Old Hollywood

Score: +1

Margaret O'Brien

as Margarita Schuyler in Hamilton in Old Hollywood

Score: +1

Dick Van Dyke

as King George III in Hamilton in Old Hollywood

Score: +1

Judy Garland

as Angelica Schuyler in Hamilton in Old Hollywood

Score: +1

Ray Charles

as Gilbert du Motier in Hamilton in Old Hollywood

Score: +1

Gordon MacRae

as George Washington in Hamilton in Old Hollywood

Score: +1

Julie Andrews

as Elizabeth Hamilton in Hamilton in Old Hollywood

Score: +1