“Oh, Pretty Woman” or “Pretty Woman” is a song recorded by Roy Orbison, written by Orbison and Bill Dees. It was released as a single in August 1964 on Monument Records and spent three weeks at number one on the Billboard Hot 100 from September 26, 1964, the second single by Orbison to top the US charts. It was also Orbison’s third single to top the UK Singles Chart (for a total of three weeks). The record ultimately sold seven million copies and marked the high point in Orbison’s career. Within months of its release, in October 1964, the single was certified gold by the RIAA. At the year’s end, Billboard ranked it the number four song of 1964.
The lyrics tell the story of a man who sees a pretty woman walking by. He yearns for her and wonders if, as beautiful as she is, she might be lonely like he is. At the last minute, she turns back and joins him. The title was inspired by Orbison’s wife, Claudette, interrupting a conversation to announce she was going out. When Orbison asked if she had enough cash, his co-writer Bill Dees interjected, “A pretty woman never needs any money.”
Orbison’s recording of the song was produced by Fred Foster. There were four guitar players on the session: Roy Orbison, Billy Sanford, Jerry Kennedy, and Wayne Moss. Sanford, who later played on sessions for Elvis Presley, Don Williams, and many others, played the intro guitar. Williams introduced him as a kid who had just arrived in Nashville, with a borrowed guitar, who heard Orbison was minus a guitar player, who went over and got the gig. Other musicians on the record included Floyd Cramer on piano, Bob Moore on an upright bass, Boots Randolph on saxophone, Charlie McCoy on harmonica, Buddy Harman on drums, and Paul Garrison on percussion. Orbison played a 12-string Epiphone. Bill Porter served as recording engineer for the song.
Orbison posthumously won the 1991 Grammy Award for Best Male Pop Vocal Performance for his live recording of “Oh 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.
In 1989, rap group 2 Live Crew recorded a parody of the Orbison song, using the alternate title “Pretty Woman”, for their album As Clean As They Wanna Be. 2 Live Crew sampled the distinctive bassline from the Orbison song, but replaced the original lyrics with talk about a hairy woman and her bald-headed friend and their appeal to the singer, as well as denunciation of a “two-timing woman.”
Orbison’s publisher, Acuff-Rose Music sued 2 Live Crew on the basis that the fair use doctrine did not permit reuse of their copyrighted material for profit. The case, Campbell v. Acuff-Rose Music, Inc. went all the way to the United States Supreme Court. The Supreme Court decided in 2 Live Crew’s favor, greatly expanding the doctrine of fair use and extending its protections to parodies created for profit. It is considered a seminal fair use decision.