Suggestions by @michelebennett

Paul Robeson

as Lando Calrissian in Star Wars Original trilogy in the 50s

James Stewart

as Luke Skywalker in Star Wars Original trilogy in the 50s

Margaret Sullavan

as Mara Jade Skywalker in Star Wars as Classic Hollywood (1950s)

Bela Lugosi

as Jorus C'Baoth in Star Wars as Classic Hollywood (1950s)

Boris Karloff

as Grand Admiral Thrawn in Star Wars as Classic Hollywood (1950s)

Paul Robeson

as Lando Calrissian in Star Wars as Classic Hollywood (1950s)

Clara Blandick

as Beru Lars in Star Wars as Classic Hollywood (1950s)

Harry Davenport

as Owen Lars in Star Wars as Classic Hollywood (1950s)

George Bancroft

as Anakin Skywalker in Star Wars as Classic Hollywood (1950s)

Gary Cooper

as Boba Fett in Star Wars as Classic Hollywood (1950s)

Edward Van Sloan

as Wilhuff Tarkin in Star Wars as Classic Hollywood (1950s)

Katharine Hepburn

as Leia Organa in Star Wars as Classic Hollywood (1950s)

James Stewart

as Luke Skywalker in Star Wars as Classic Hollywood (1950s)

Samuel S. Hinds

as Obi-wan Kenobi in Star Wars as Classic Hollywood (1950s)

James Stewart

as Han Solo in Star Wars as Classic Hollywood (1950s)

Gary Cooper

as Boba Fett in Star Wars (1950's)

Margaret Sullavan

as Mara Jade in Star Wars (1950's)

Katharine Hepburn

as Princess Leia Organa in Star Wars (1950's)

James Stewart

as Luke Skywalker in Star Wars (1950's)

John Barrymore

as The Riddler in My version of Batman (Golden Age)