3. Breakfast at Tiffany's
Another one that leaves a lot of people red-faced, Breakfast At Tiffany's is an excellent film for the most part, tainted slightly by Mickey Rooney's ridiculous portrayal of the Asian man "Mr. Yunioshi", wearing glasses, prosthetic make-up and a mouthpiece (giving him bigger teeth) in order to more closely resemble a stereotypical caricature of Japanese people. In the decades since its release, it remains its most frequently-maligned component, all the more frustrating given how well-judged everything else in the film is. Director Blake Edwards did in later years respond to the criticism, wishing that he had just cast a Japanese actor in the role instead, while Rooney, devastated by the criticism, has expressed similar sentiment. It's a debate that feels fresh in the mind given the race-changing make-up effects in the Wachowski's upcoming Cloud Atlas, but at least in that film it doesn't serve to reinforce stereotype, and also has a narrative point.