"Oh, Pretty Woman" is a song, released in 1964, which was a worldwide success for Roy Orbison. Recorded on the Monument Records label in Nashville, Tennessee, it was written by Roy Orbison and Bill Dees. The song spent three weeks at number one on the Hot 100. The best-known guitar performance was by Wayne Moss later of Barefoot Jerry. Although the official recording appeared in 1964, the Beatles recalled Orbison's having written and performed the song during a mid-1963 tour of the UK which included both acts.

Orbison posthumously won the 1991 Grammy Award for Best Male Pop Vocal Performance for his live recording of the song 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 Stonemagazine ranked it #222 on their list of the "500 Greatest Songs of All Time."

The lyrics tells 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 was okay for cash, his co-writer Bill Dees interjected "A pretty woman never needs any money."

In 1989, the controversial rap group 2 Live Crew recorded a parody of the Orbison song, using the alternate title "Pretty Woman" for their album Clean As They Wanna Be. The 2 Live Crew sampled the distinctive bassline from the Orbison song, but the romantic lyrics were replaced by 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.

The song has been covered by a number of artists: