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Michael Jackson; 2002
This was hard to watch. First, it involves not only Michael Jackson thinking that a tacky, glittery piece of crap was an award for being "Artist of the Millennium," which led to him making a terribly sincere speech. But also? Britney Spears is wearing some really unfortunate black leather gear (including a truly tragic hat) that just makes her look like the lamest dominatrix ever. Awful. Especially because the girl can NOT walk in heels. Like, at all. But really, the worst part is when Michael thanks David Blaine because "his magic is real" and Michael "believes in him."