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40. "La Isla Bonita" (from 'True Blue,' 1986)

"La Isla Bonita" was unlike anything Madonna had recorded before, a Latin-tinged uptempo ballad complete with Spanish guitar, Cuban percussion and lyrics that explored dreams of exotic San Pedro. Madonna wrote the song with Patrick Leonard and Bruce Gaitsch. "She's very good at finding a lyrical theme that fits the mood of the music," Leonard recalled. He originally penned "La Isla Bonita" for Michael Jackson (whom he'd previously worked with on the Jacksons' Victory tour and album). But Jackson didn't like the title, so Leonard tried it out on Madonna, who tailored the lyrics to fit her own idea of "the beauty and mystery of Latin American people." "I don't know where that came from," she told Rolling Stone years later, in reference to the song's specific imagery. "I don't know where San Pedro is. At that point, I wasn't a person who went on holidays to beautiful islands. I may have been on the way to the studio and seen an exit ramp for San Pedro." The video, in which she played a flamenco dancer, was one of her most theatrical Eighties clips, and its drama has impacted many of her inheritors – Lady Gaga famously ripped it off for her 2009 hit "Alejandro."