Late Serge Gainsbourg: and late Taylor Swift: The chiaroscuro, the black and white, the head-and-shoulder shot, the dark lipstick, the mousse, the eye shadow, the one ear visible (the other only in silhouette), signifiers of a jaded femininity.
Oh wow, I was just looking through some Slumberland stuff and came across that. Here's a couple more: Kristin Kontrol - X-Communicate/Peter Murphy - Deep
The Monkees - ??? OK, maybe this was just a publicity photo and not cover art. I don't know where it comes from, but I just saw it here (25/3/14 - The Monkees - Alternate Title - 1967 - In Deep Music Archive ) and I instantly thought of this... Talking Heads - Little Creatures (rear cover)
Probably been posted already, thread isn't searchable ... Ornette Coleman - Ornette! (1962) Clinic - Internal Wrangler (2000)