IN 1985, French photographer Jean-Baptiste Mondino saved the plummeting career of singer Don Henley by directing the video for "The Boys of Summer." The moody, atmospheric work captured the superficiality of LA and the dark underbelly of love, and it swept the MTV Video Music Awards, putting Mondino on the radar of high-profile artists such as Prince, Bryan Ferry, Sting, David Bowie, and Neneh Cherry. But his best work was in collaboration with Madonna. She was the hyper-sexualized muse that took his work to the next level, while he provided her with some of the best videos of her career.

"Open Your Heart" (1986)—While this song may lyrically depict the standard boy-meets-girl scenario, Mondino flipped the script by depicting Madonna in a peep show setting, pursued by pathetic voyeurs and one fresh-faced boy who never makes it inside. Dressed in a sexy version of Sally Bowles' corset from Cabaret, this is one of the earliest examples of Madonna's laser-beam sexual power. Even behind glass, Madonna controls the situation, shooting down customers' "male gaze" with her own steely glare. Mondino continues the gender-flipping antics with Madonna and her young admirer running away together—both dressed in men's suits. Fun fact: Then-hubby Sean Penn was originally supposed to direct the video, but Baptiste stepped in at the last minute. The world is eternally grateful.

"Justify My Love" (1990)—Madonna's favorite video of her career was also one of the most controversial, as well as the flat-out sexiest. (It also features her best acting to date.) Filmed by Mondino in luminous black and white at a Parisian hotel, "Justify My Love" melds trip-hop beats with Madonna's spoken lyrics, and an impressive array of sexual situations including BDSM, bisexuality, androgyny, cuckolding, latex play, and group sex—with her usual doses of Catholicism and power plays tossed in for good measure. Naturally, it was banned from MTV, and drove everyone INSANE. Viewed today, it is absolutely gorgeous, unrepentantly hot, and an early inspiration for the anti-slut-shaming movement.

"Human Nature" (1995)—This is the perfect Madonna video: sexually adventurous and cheeky, with amazing dance moves and a big, healthy dose of "fuck you." Leading up to this, Madonna had been heavily criticized for her coffee-table porn book, Sex, her album Erotica, a filthy appearance on David Letterman, and her role in the erotic thriller Body of Evidence. Did this outpouring of animosity cow Madonna? HELL NO. She and Mondino came out of the gate swinging, with a perfectly choreographed, latex- and leather-filled bondage shindig, in which Madonna celebrates/makes fun of sex while seducing/laughing at her critics. When she faces the camera at the end of the video and sneers, "Absolutely no regrets!"—you absolutely believe it.

"Love Don't Live Here Anymore" (1996)—Filmed during Madonna's one-day break from the set of Evita, Mondino obviously did the best he could in a limited amount of time. "Love Don't Live Here Anymore" is a sepia-toned single-shot video that slowly pushes in on Madonna as she sadly circles and gyrates on a large pillar in an abandoned hotel. It's very pretty, and the ache behind Madonna's eyes is palpable and gorgeous—but otherwise? It's just okay.

"Don't Tell Me" (2000)—Even sans video, this is a freaking great song. (Perhaps the last great song of her career?) A stuttering combo of trip-hop and hillbilly folk, Madonna's soulful croon perfectly expresses the longing of a gal telling her beau to stop controlling how she feels. But the video departs from Mondino and Madonna's earlier collaborations, because here, the icon is treated more like a setpiece. "Don't Tell Me" hearkens back to the director's work on "The Boys of Summer" with topsy-turvy projections and a placid, near-emotionless narrator. Mondino's jerky images of cowboy life expertly mirror the stutterstep of the music, while subtly puncturing the mythos of the American West. Meanwhile Madonna is just there—not overtly sexual, not trying to prove any point—because the real work's already been done in recording this freaking great song.

"Hollywood" (2003)—This one may be unfamiliar, because by the early 2000s MTV had stopped playing videos. And maybe it's just as well in this case, because the Madonna-Mondino team had already created their greatest works. "Hollywood" is neither lyrically nor sonically impressive, and while the video stretches to make a deeper point about the vagaries of LA life—that's what it feels like. A stretch. It's nicely shot, well edited, and reminiscent of Mondino's earlier work without breaking any new ground. In 2006, OK Go saw their choreographed treadmill video "Here It Goes Again" become a smash on YouTube, and a new era of music videos began. It was one that left Madonna and her most reliable collaborator, Jean Baptiste-Mondino, far behind—relics of a former age.

Oh, but what an age it was.

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