According to Bill Dees, Orbison's songwriting partner, they were in the process of writing some music when 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 said: "A pretty woman never needs any money." Inspired, Orbison started singing, "Pretty woman walking down the street."
The song was written on a Friday, the next Friday it was recorded, and the next Friday it was out.
Roy Orbison explained what was going on in the song "There's a ballad in the mid-section of it there: he's very sure of getting the girl when he first sees her, and then he's not so sure, and then he gets desperate, and then he says forget it, and then she comes back. It's quite complicated, but it's probably in the presentation, or if I'm really singing like I know I can and I'm doing the job that I should be doing, then it could be that the voice quality in parts has a melancholy something."
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. They would remarry in 1966.
In 1964, Orbison was the only American artist to have a #1 UK hit, and he did it twice - with "(Oh) Pretty Woman" and "It's Over."
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