Correct me if I'm remembering wrong but didn't SNL have Fred Armisen as their first Obama impersonator in 2008 and 2009? And he wore makeup to darken his skin. I do think there's a difference between what Al Jolson did and what Jimmy Kimmel did. If the makeup is well done, you just look like an actual black person, not an ugly caricature. That said, no average parent is going to have the time, skill, or patience to tastefully change their kid's racefor Halloween. The Diana Rosses that Kelly remembers seeing were almost certainly poorly done and would have come across as disrespectful and ugly to many people.

I remember dying my hair orange one Halloween and spending all afternoon listening to a cassette tape on how to sound Irish. I got a few laughs at the Halloween party I went to in Orlando. We were all under 21 and there was no alcohol at this party. My Irish character, Fitzmichael, did not say anything about alcohol at the party. He just acted goofy and had a completely overdone accent. Maybe offensively overdone. And his hair was neon orange, since party City didn't have natural orange that day. So a girl my age that I'd never met before said that she was offended. I asked why, trying to stay in character. I expected her to say that she knew some actual Irish people and their accent was much less ridiculous. Instead, she said that I was making it like all Irish people are drunk. I said, only one of us said anything about Irish people being drunk and it's you. She walked away, never saw her again.

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