Song She Inspired: Billy Joel - "Uptown Girl" (1983)
Highest Position on the Billboard Hot 100: 3

If you've seen the video for the song, you may have the impression that Billy Joel, who cannot be accused of being a handsome man, wrote "Uptown Girl" for his supermodel girlfriend (soon to be wife) Christie Brinkley. That's only half true. It turns out, the story is even more jealousy-inducing.

Joel started writing the song while he was dating a 19-year-old Australian model named Elle MacPherson. After that relationship ended, Joel took up with Christie Brinkley. The song as finished was about Christie. So it's not the story of a shlubby rock star scoring a supermodel, it's the story of a shlubby rock star scoring two supermodels. Damn you, Joel.