Girl 6 - 35MM

Spike Lee’s underrated black comedy about female workplace empowerment casts Theresa Randle as Judy, an aspiring ingénue turned “friendly phone line” operator. Madonna’s brief, hilarious cameo as sizzling hot “Boss #3” spotlights her sailor mouth as she lists off the various turn-ons and fetishes demanded by her clients (“Shitting’s really big right now… don’t ask me why.”). Girl 6 also stars Spike as Judy’s baseball-memorabilia-obsessed best friend and features appearances by Debi Mazar, Naomi Campbell, Halle Berry, John Turturro, and Quentin Tarantino… and an all-Prince soundtrack.

Video: HUMAN NATURE (Jean-Baptiste Mondino, 1995)

Jean-Baptiste Mondino, who Madonna called “my favorite director in the whole world,” evokes Kubrickian sci-fi and S&M sleek in this homage to the kinky pin-up art of Eric Stanton. With fiercely dynamic, innovative choreography by Jamie King (who would direct multiple tours and M’s Super Bowl halftime show), Matthew Rettenmund suggests, “If it’s possible for one video to sum up Madonna’s Madonna-ness, “Human Nature” is that video.”