Aisha Harris' article, "A Brief Guide to 21st Century Blackface", is a MUST READ. She breaks down the different ways blackface shows up in media, from (attempted) satire to "is this blackface?" moments when an actor's skin is darkened for (maybe?) other reasons.
She points out where these various excuses generally fall short, as well as one example that works: Spike Lee's film Bamboozled. In the end, she suggests that all of this doesn't mean you never, ever engage with blackface in art, but that you have to know what you're doing with it, why you're doing it, if you're using the right context, and to really, really ask yourself if you're going to do it well.
"While nothing made in the last 20 years comes close to Mr. Lee’s film in terms of acutely exposing the folly, vice and stupidity of blackface onscreen, what this look back reveals is that quite frequently there has at least been an attempt on behalf of creators to engage in critique. Some went the Mickey-and-Judy route, treating it like an old comedic pastime with nary a thought to its racist roots, but many showed signs of nuance and acknowledgment, even if the execution fell flat."
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