9. Oh Pretty Woman by Roy Orbison and Bill Dees (1964)
One of the best ways to rake in big cash on your songwriting skills is for your song to be part of a movie’s soundtrack, or better yet for it to be the feature song in a blockbuster Hollywood movie. That is what happened to this song and to add to the fame and fortune, the movie was named after the song.
Bill Dees did an interview in 2012, just before his death and stated that he was still earning $100-$200 thousand per year in royalties from Oh Pretty Woman, nearly 50 years after he penned it. The estimated value of the song is $19.75 million.
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