6. Queen, "I Want To Break Free"
In the UK, a man in a dress = comedy! The band are dressed as characters from Coronation Street--when the video isn't totally insane, that is. Freddie Mercury deigned to shave his moustache for the crazy ballet bit, but not the bit where he's wearing a skirt. Still, I appreciate the effort; it's slightly more popular to get someone in to dress as a lady rather than do it yourself, so I'll take any band in drag that I can get. (And Roger Taylor makes a great chick.)
Brian May blames this video for destroying the band's career in America, as MTV banned it for seven years. I guess they thought alternative sexualities were even scarier than black people.
5. David Bowie, "Boys Keep Swinging"
Some artists are reluctant to get all kitted out as a woman once, but Mr. Bowie is awesome enough to do it three times in one video. Personally, I favor the sassy brunette, but I'm sure cases could be made for the other two. What more is there to say about "Boys Keep Swinging," really? The video's nuts, but certainly not the craziest Bowie video there is. Bless him.
My absolute favorite thing about this song is that one of the perks of manhood listed is "They'll never clone you!" Because I worry about that a lot, you know.
4. U2, "One"
Most of the queer interpretations of "One" spring from this video. Yes, a lot of the money they made on the singles went to AIDS charities, and in 1991 AIDS was still The Gay Disease, but really. Here we've got the whole band in drag, and Bono's singing to his dad. (Like, literally--his dad's in the video.) Adds another layer to the lyrics, doesn't it?
Unfortunately, they aren't attractive or enthusiastic; drummer Larry Mullen expressed his displeasure at being forced to dress like a woman by sulking and refusing to remove his Doc Martens. It's borderline terrible of him (seriously, Larry! It's just a feather boa! What's your damage?), but also freaking hilarious, because he is so not even trying to look anything but infuriated.
Adam Clayton is having a damn good time, though.