4. Mickey Rooney (Breakfast At Tiffany's)
Like John Wayne, Mickey Rooney lands on our list for his shameless use of yellowface for his role as Mr. Yunioshi in 1961's Breakfast at Tiffany's. Rooney went overboard portraying a caricature of a Japanese man, wearing makeup and a prosthetic mouthpiece to make him appear Asian. At the time of its release, the hideously racist character didn't cause much of a stir. But, in the 1990s, people began to take offensive at the patently racist character. Breakfast at Tiffany's reputation suffered a hit that ruined its legacy. The producer of Breakfast at Tiffany's, Richard Shepherd, apologized repeatedly for Rooney's insensitive portrayal and on the dvd commentary for Breakfast at Tiffany's Anniversary, apologizes profusely for it over and over again. Rooney himself said that he wouldn't have taken the role if he knew how offended people would be. Rooney's miscasting was severe enough to tarnish the legacy of a classic film.