Not only did two of the Wayans brothers go lady for this ridiculous send-up, they also turned themselves into the most ridiculous of white ladies. Extra points to the pair for taking down silly socialites (looking at you, Paris and Nikki!) along the way.
9 of 13
10 of 13
11 of 13
12 of 13
13 of 13
Mickey Rooney Breakfast at Tiffany's (1961)
For a film that boasts so much class (That black dress! That dreamy ''Moon River'' rendition!), it's hard to believe Tiffany's producers would stoop so low by casting Mickey Rooney as Holly's stereotypical Japanese neighbor. Not only was he not the slightest bit believable as a native Japanese speaker in the 1961 classic, but he managed to offend droves of film critics and moviegoers as well. —Kate Ward