Suggestions by @michelebennett

Rock Hudson

as Darth Vader in Star Wars: Episode V - The Empire Strikes Back (1980)

Clint Eastwood

as Boba Fett in Star Wars: Episode V - The Empire Strikes Back (1980)

Basil Rathbone

as Ki Adi Mundi in Star Wars Prequel Trilogy (1960s)

Stepin Fetchit

as Jar Jar Binks in Star Wars Prequel Trilogy (1960s)

Jean Simmons

as Padmé Amidala in Star Wars: Episode I – The Phantom Menace (1959)

Paul Robeson

as Captain Quarsh Panaka in Star Wars: Episode I – The Phantom Menace (1959)

Dudley Digges

as The Kingpin in Marvel Cinematic Universe (Golden Age of Hollywood)

Dudley Digges

as 1879 in Best Actor/Actress by year of birth

C. Aubrey Smith

as Obi-Wan Kenobi in Star Wars: Episode VI – Return of the Jedi (1943)

Ray Bolger

as C-3PO in Star Wars: Episode VI – Return of the Jedi (1943)

Jerry Maren

as R2-D2 in Star Wars: Episode VI – Return of the Jedi (1943)

Cary Grant

as Han Solo in Star Wars: Episode VI – Return of the Jedi (1943)

Edward Everett Horton

as The Voice of Jabba in Star Wars: Episode VI – Return of the Jedi (1943)

Ed Wynn

as Yoda in Star Wars: Episode VI – Return of the Jedi (1943)

Katharine Hepburn

as Princess Leia in Star Wars: Episode VI – Return of the Jedi (1943)

James Stewart

as Luke Skywalker in Star Wars: Episode VI – Return of the Jedi (1943)

Ed Wynn

as Yoda in The Empire Strikes Back (1940)

James Stewart

as Luke Skywalker in The Empire Strikes Back (1940)

Ray Bolger

as C-3PO in The Empire Strikes Back (1940)

Paul Robeson

as Lando Calrissian in The Empire Strikes Back (1940)