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Director: Herb Ritts
Why: Legendary photographer Herb Ritts only made 12 music videos before succumbing to pneumonia at the age of 50, but his first three were groundbreaking classics. "Cherish," with Madonna, "Love Will Never Do (WIthout You)" with Janet Jackson and "Wicket Game" with Chris Isaak. Madonna actually insisted he direct "Cherish" - his first film - and her instincts were spot on. It's a stunning juxtaposition of nude merman swimming through the high waves of the pacific ocean as Madonna falls for the charms of a young mer-boy on the beach all gloriously shot in black and white. This was also Madonna's second video in a row with either intended or unintended homoerotic imagery (after "Express Yourself") and foreshadowed the risks she'd take over the next decade.