Retro: Sorority Boys

This was not a good movie, but some of the themes were worthwhile and the gurls sometimes looked nice:

Retro: The Crying Game

 Jaye Davidson was nominated for an Oscar for this performance. 

Retro: Bosom Buddies

 When Cillian Murphy won the Oscar for Oppenheimer, I noted that the talented actor had femulated in multiple films. Tom Hanks, of course, has multiple acting Oscars and began his career in a dress. I'm guessing many young people in the community don't know that.

Here's a peek at the credits:

It seems very difficult to find any more substantial videos of the performance en femme. 

Retro: The Odds

From 1993, it's "Heterosexual Man" featuring video appearances from some members of Kids in the Hall. Spoiler: towards the end of the video the entire band femulates. 

Here's an image of Dave Foley from the video. 

Retro: David Bowie

David Bowie - Rebel Rebel • Top of the Pops. Anyone know of a live action video that feature's the song's story?

 

Retro: The Kinks

The Kinks - Lola (Official Music Video). Does anyone know of a live action video of this song that is not merely from a concert or TV program?

 

Retro: Lou Reed

Lou Reed - Walk On The Wild Side, with help from some of Andy Warhol's superstars.