I'm given to understand that the use of of blackface is potentially offensive because back in the early days of theatre, black people weren't allowed on stage. If any role required a black person, it would require a white actor to dress up in blackface to portray a black person - generally in the role of savage/dumbass/object of ridicule. Blackface was pretty blatant and offensive caricature.
I don't think there's anything specifically offensive about about white guy dressing up as as a specific black guy. But unless you can pull it off really, really well - you run the risk of looking like a dumbass in blackface.
But then, I'm neither black, nor a theatre-buff. I could be wrong.
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