1. Robyn -- "U Should Know Better" ft. Snoop Dogg
Robyn herself does not cross-dress, but a little boy basically plays her, and a woman plays Snoop Dogg.
Boy-Robyn has her signature moves down:
And Robyn herself shows up as Boy-Robyn's mom.
Robyn's experiences of being misgendered were fodder for the video:
It happens to the best of us, Robyn.
2. Jessie J -- "Do It Like A Dude"
OK, the whole song is based on defying gender roles. But this is a very important moment:
And then she grabs her crotch a lot.
Also, this happens, so.
3. Eurythmics -- "Who's That Girl"
Seeing Annie Lennox looking this feminine is already sort of surprising, since she's usually androgynous:
But Annie in drag shows up at the very end:
And then this totally realistic-looking kiss happens.
4. Ciara -- "Like A Boy"
She has the macho posturing down.
And it really works for her.
She dances with herself in a suit and a dress:
And repeatedly grabs her crotch:
There seems to be a theme emerging.