Roy Orbison – Oh, Pretty Woman (1965)

"OH, PRETTY WOMAN" - Roy Orbison on American Bandstand 1966

Roy Orbison was writing with his songwriting partner Bill Dees at his house when he told Dees to get started writing by playing anything that came to mind. Orbison’s wife Claudette came in and said she was going to go into town to buy something. Orbison asked if she needed any money, and Dees cracked, “Pretty woman never needs any money.” Inspired, Orbison started singing, “Pretty woman walking down the street.”

Bill Dees recalls:

“He sang it while I was banging my hand down on the table and by the time she returned we had the song. I love the song. From the moment that the rhythm started, I could hear the heels clicking on the pavement, click, click, the pretty woman walking down the street, in a yellow skirt and red shoes.

We wrote Oh Pretty Woman on a Friday, the next Friday we recorded it, and the next Friday it was out. It was the fastest thing I ever saw. Actually, the yeah, yeah, yeah in Oh Pretty Woman probably came from The Beatles.”

In the same book Bill Dees recounts how the distinctive growling cry of “Mercy” came about: “I can’t do that growl like Roy, but the “Mercy” is mine. I used to say that all the time when I saw a pretty woman or had some good food. Still do.”

Orbison and his wife Claudette had recently reconciled after some tough times, but as this song was climbing the charts, Roy found out she had been cheating on him and filed for divorce. In 1966, they remarried, but two months later Claudette was killed when the motorcycle she was riding was hit by a truck. Orbison faced tragedy again when his two oldest sons died in a fire at his home in 1968. He was on tour at the time.

Orbison posthumously won the 1991 Grammy Award for Best Male Pop Vocal Performance for his live recording of “Pretty Woman” on his HBO television special Roy Orbison and Friends, A Black and White Night. In 1999, the song was honored with a Grammy Hall of Fame Award and was named one of the Rock and Roll Hall of Fame’s 500 Songs that Shaped Rock and Roll. In 2004, Rolling Stone magazine ranked it #224 on their list of the “500 Greatest Songs of All Time.” On May 14, 2008, The Library of Congress selected the song for preservation in the National Recording Registry.

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