Suggestions by @jamesthethinker

Lara Croft

as Elizabeth Taylor in Characters golden age stars could have played

Professor Rubeus Hagrid

as Sydney Greenstreet in Characters golden age stars could have played

FAKE

as Sydney Greenstreet in Characters golden age stars could have played

Cinderella (Disney Character)

as Grace Kelly in Characters golden age stars could have played

Tinker Bell (Disney Character)

as Marilyn Monroe in Characters golden age stars could have played

Lightning McQueen

as James Dean in Characters golden age stars could have played

Harley Quinn (Dr. Harleen Quinzel)

as Lucille Ball in Characters golden age stars could have played

Mary Poppins

as Audrey Hepburn in Characters golden age stars could have played

Sheriff Woody Pride

as Roy Rogers in Characters golden age stars could have played

Axel Foley

as Eddie "Rochester" Anderson in Characters golden age stars could have played

Wonder Woman (Diana Prince)

as Hedy Lamarr in Characters golden age stars could have played

David S. Pumpkins

as Red Skelton in Characters golden age stars could have played

Batman

as Humphrey Bogart in Characters golden age stars could have played

Don Draper

as Humphrey Bogart in Characters golden age stars could have played

Commander Shepard

as Rita Hayworth in Characters golden age stars could have played

Bond Girl (James Bond)

as Audrey Hepburn in Characters golden age stars could have played

Groot

as John Wayne in Characters golden age stars could have played

Amanda Waller

as Hattie McDaniel in Characters golden age stars could have played

Emperor Sheev Palpatine (Darth Sidious)

as Lon Chaney in Characters golden age stars could have played

Princess Peach Toadstool

as Marilyn Monroe in Characters golden age stars could have played