10. Nine Inch Nails, "Starfuckers, Inc."
Universal Music fails too hard to allow embedding, so you'll have to click to watch this one.
I wasn't sure if I wanted to include this one, because it doesn't have a very gay aesthetic. Within the video's narrative, the crossdressing is less "drag queen" and more "it's a trap!" It's still very campy, though, and I do love me some silliness.
What really launches it into "drag" for me is how devoted Marilyn Manson is to playing his character. The man flails and wobbles like he's been waiting to pretend to be a lushy socialite his entire life, and I have to admit, he's damn good at it.
9. The Dresden Dolls, "Shores Of California"
Some people have made a case for Amanda Palmer's touch of menswear in this video counting as drag, which... no, not really. It just highlights her femininity and adds another queer little twist to the song.
What does count as drag is a guest appearance by Kelly! I am wholeheartedly for videos where ANYONE makes out with a drag queen. They just don't get enough lovin', you know.
8. Annie Lennox, "Little Bird"
Annie drag! I don't mean "Annie in drag;" I mean "people impersonating Annie Lennox." Specifically, people impersonating characters that she's portrayed in other music videos. All the bases are covered: you've got girls dressed as girls, boys dressed as Annie dressed as boys, and a whole pile of androgyny to sort through. This is a great one to watch with your friends and play Spot The Queen.
The highlight, of course, is Lennox herself as she turns the flame up to 11. Smile harder, Annie! I don't think they can see those teeth on Mars yet.
7. Suede, "Attitude"
This was Suede's last single, so I guess they decided to go out in a blaze of "We're STILL CAMP you guys! SERIOUSLY. WE ARE." And you're not imagining things: the queen here is John Hurt, of 1984 and V for Vendetta fame. I'm not entirely sure how this came to pass, as neither the video concept nor the casting make any intuitive sense to me, but you should be fine as long as you don't think about it too hard.
Hurt isn't in extreme drag in this one, which is part of the charm--he's not dressed to the nines, but his camp performance more than conveys a nice female-impersonatey aesthetic. Plus, I love how he sings to himself; that's really how we all do it, isn't it?
The song was also featured in an episode of the US Queer as Folk, so I guess this is their faggiest single since "Can't Get Enough."