1. Mickey Rooney – Breakfast At Tiffany’s (1961)
2. Leonardo DiCaprio – J. Edgar (2011)
3. Jim Sturgess – Cloud Atlas (2012)
4. Shawn & Marlon Wayans – White Chicks (2004)
5. Al Jolson – The Jazz Singer (1927)
Contributed by: Spencer
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Shadows & Noise 
This list seems like it was more difficult than initially meets the eye due to the necessary balancing of make-up that is simply awful versus outrageously racist. I think you managed this really well, but I’m curious about your thought process.
Did you see Cloud Atlas? Honestly, I could’ve done the entire list using just that movie. Jim Sturgess in yellowface was the most egregious example, but they also have Hugo Weaving as a woman, Asian actress Doona Bae as a Hispanic woman, and Tom Hanks as a reject from Color Me Badd. In the movie’s defense, this was because the whole point of the film is that each actor is playing a character in multiple settings and time periods, as reincarnations of a sort. I get that. But the idea, while ambitious, just doesn’t end up working at all.
As for the rest of my list, bad racial makeup was obviously an easy target — that explains Rooney and Jolson. (Had to include a blackface in here … you could also go with Fred Astaire in Swing Time). “White Chicks” wasn’t offensive so much as just bad. And J. Edgar — well, the makeup job in that was so bad that it was the single reason I refused to watch the movie. (Part of the problem was in casting Leo anyway….)
One nominee I really wanted to include, but couldn’t make room for, was John Travolta in “Battlefield Earth.” Anyone else you think I missed?
I’ve haven’t seen Cloud Atlas! With all the bad reviews I’ve heard, I’ve never had the desire to check it out. I’ve considered reading the book instead, but much better stuff keeps topping my list.
No, I can’t think of anyone else you missed. When I read the title to the High-Fiver, I immediately thought of J. Edgar, so I was pleased to see it take a prominent spot. What piqued my interest was the location of the bad racial make-up as selections at 1 and 5, leaving me to think that purely bad racial make-up wasn’t entirely enough to move up the list, unless there was something more. But, now knowing about Cloud Atlas, I see that there was an element of bad racial make-up there too, along with the make-up just being, well, bad.