On this day 62 years ago, Roy Orbison, who Elvis Presley claimed had a “perfect voice” and called him the “greatest singer in the world” released one of his signature songs.
Dolly Parton concurred, revealing high praise for Orbison when she said, “I’ve never been more moved by a voice than I have been by Roy Orbison. I loved him personally and I loved his voice. I think of him often and frequently listen to his songs.”
“Oh, Pretty Woman” was released on Aug. 29, 1964 and would become one of his greatest tracks, reaching No. 1 on the Billboard Charts less than a month later on Sept. 26, 1964. The song remained on the charts for 15 weeks and was the final No. 1 for the iconic singer.
‘Oh, Pretty Woman’ Idea Was Sparked by Orbison’s Wife
American Songwriter revealed the impetus for the song came while Orbison and songwriter and collaborator Bill Dees were working on new music together. After Orbison noticed his wife, Claudette Frady, getting ready to go into town, he asked if she needed any money.
Dees chimed in, “Pretty woman never needs any money,” and a hit was born.
“He sang it while I was banging my hand down on the table and by the time she returned, we had the song,” said Dees in the 2005 book 1000 UK #1 Hits. “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.”
He continued, “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.”
Rolling Stone ranked the song No. 224 on its list of the 500 greatest songs of all time.
Related: One of the Greatest Guitar Solos of All Time Belongs to 1976 Hit – And It Still Rocks
This story was originally published by Men’s Journal on Aug 29, 2026, where it first appeared in the News section. Add Men’s Journal as a Preferred Source by clicking here.