Aphex Twin on MTV (1996)

Perhaps the most intriguing thing is how the girl seems to be, like, in love with him or something.

New Wave on 20/20 (1979)

Could you imagine a mainstream news piece getting it this (almost) on the mark nowadays? Also, a nice companion to Retromania, noting the undeniable debt of punk/new wave to the 1950s.

David Bowie- "Crystal Japan" video

The commercial that wound up being the origin of "Crystal Japan", the Bowie b-side that Nine Inch Nails eventually knicked for "A Warm Place"

David Bowie- Boys Keep Swinging (Saturday Night Live, 1979)

Starring Klaus Nomi
This has to be the strangest SNL performance ever.
As noted in the user comments for this video, the phobic SNL crew decided to cut out the phrase "other boys check you out", but failed to censor the puppet erection he made for his marionette costume.