10. "Cherish" (1989)
The photographer Herb Ritts and Madonna struck up a friendship early in Madonna's career, with Ritts shooting the glammed-out cover for the 1986 album True Blue and photographs for Rolling Stone — including the cover for the September 10, 1987 issue. But what Madonna really wanted Ritts to do was direct. "She kept asking me, and I said I really didn't know the first thing about moving imagery," Ritts told the art curator François Quintin in a 1999 interview. "Finally, I practiced with a little Super 8 camera when I was on a job in Hawaii, and came back and said I could do it. Two weeks later, I was filming 'Cherish.' I directed it and did the camera work as well. It was invigorating." Madonna was pretty invigorated by the black-and-white, mermen-filled shoot as well: "I made her dive into the freezing ocean. She was a real trooper," the late Ritts told the Toronto Star in 1990. The playful video became an MTV staple, a light jaunt on the beach after the controversy-drenched "Like A Prayer" and the future-shocked "Express Yourself." Ritts went back to the beach when he directed the videos for Janet Jackson's joyful "Love Will Never Do (Without You)" and Chris Isaak's brooding "Wicked Game."