I.Y. Yunioshi in Breakfast at Tiffany's (1961)
Portrayed by: Mickey Rooney
Breakfast at Tiffany’s has been romanticized to death by entire generations of filmgoers since its release. Which is weird, because it contains one of the most offensive performances in the history of American movies. Not only was Mickey Rooney cast to portray a Japanese man, the character itself indulges so many stereotypes about people of Asian descent, it would've still been offensive had an actual Japanese actor been cast.
The same way minstrel shows showcased overtly racist slapstick comedy featuring performers in blackface, Rooney’s role as I.Y. Yunioshi was a majorly exaggerated caricature of people of Japanese descent.