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I came into the office this morning and had this video sitting, innocently, in my inbox:

At first glance, there’s nothing particularly curious about it. It’s blatantly racist. 5 guys in blackface, dancing around minstrel-style to some Jackson Five lyrics. This isn’t anything new, but perhaps moreso than in cultures across the planet, the United States has implicitly outlawed such “buffoonery.” What can pass as cheaply humorous in Australia is downright unacceptable here in the U.S.A. We, as a society, have unanimously decided that when white men paint their faces black in order to “entertain,” it is always in poor taste and is never actually funny.

…Or is it? Even Harry Connick, Jr., a judge on the above show who voiced his offense at the end of the clip, had his very own blackface-moment on Mad TV:

Sure, his black-face isn’t that, well… Black. But, the inflection is on point. No surprise either since Connick, Jr. was brought up in New Orleans and leans heavy on jazz culture. So, is it acceptable for a white actor to successfully play a Black character? Is it only okay for a serious role and not for a comedic one that could be confused as being antagonistic?

How about when roles are reversed? Is it never entertaining when a Black actor plays a white person, a la Eddie Murphy on his Delirious comedy tape?:

You’re laughing, aren’t you? Stop lyin!

And what about all those Obama impersonators out there, the most famous of which isn’t even Black! (Fred Armisen on SNL.) He’s not Black but he plays a Black man – not just ANY Black man, but the Black President of the United States! And it’s totally not funny! YET, no one raises concerns about his blackface. Have you seen AlphaCat? Much much funnier:

So is the degree of offense taken based on the actual comedic quality of the blackface impersonation? Or is blackface just ALWAYS out of line? And if blackface is ALWAYS out of line, should Whiteface be outlawed as well? Where do we draw the line on this?

As you ponder these questions, I leave you with one of the most disturbing and, yet, most brilliantly executed blackface moments of contemporary film. HAHA!: