Songfacts®:

• Madonna wrote this song with Patrick Leonard, a musician who tends to stay out of the spotlight, but has done production and session work for many notable artists, including Rod Stewart and Elton John. His collaborations with Madonna are among her most successful: "Like A Prayer," "Who's That Girl," "Live To Tell." Madonna's lyrics on "Cherish" are about her then-husband, actor Sean Penn. By the time the song was released, they were in the middle of their divorce. >>>

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• The video, shot at Paradise Cove Beach in Malibu, California, was directed by Herb Ritts, who took the cover photo of Madonna's True Blue album. It was the first video Ritts directed, and it introduced a style he became known for: black and white on the beach, although the "Cherish" video has mermen. Ritts went on to direct the videos for "Wicked Game" and "Love Will Never Do (Without You)."
• Madonna admitted to Rolling Stone : "I've never been a good judge of what things are going to be huge or not. The songs that I think are the most retarded songs I've written, like 'Cherish,' end up being the biggest hits."
• "Cherish" spent two weeks stuck at #2 on the Billboard Hot 100 in October 1989, held off the top spot by Janet Jackson's "Miss You Much." Four years earlier, Kool & The Gang suffered the exact same fate with their own, completely different song called "Cherish," which spent three weeks at #2 in the fall of 1985 while Dire Straits held #1 with "Money For Nothing." The title had better luck back in 1966, when The Association took their "Cherish" all the way to #1.
  
  Adding another curious connection, both the Kool & The Gang and Madonna "Cherish" songs have beachside music videos, leaving both acts at #2 with sand between their toes.