Paul McCartney said Roy Orbison’s “Oh, Pretty Woman” came together while The Beatles watched. However, one of the song’s co-writers had a story that completely contradicts Paul’s. Notably, the song had an impact on cinema.
In the 1997 book Paul McCartney: Many Years From Now, Paul discussed going on tour during The Beatles’ early days. “We were starting to meet other musicians then and we’d start to see other people writing,” he recalled.
“After that, on another tour bus with Roy Orbison, we saw Roy sitting in the back of the bus, writing ‘Pretty Woman,'” he said. “It was lovely. We could trade off with each other. This was our real start.”
During a 2011 interview with MusicRadar, the song’s co-writer, Bill Dees, told a different story. He said Orbison’s first wife, Claudette Orbison, inspired the song. Dees remembered Claudette asking her husband for some money so she could go shopping.
“Then they walked off about 15 or 20 foot and it was all kissy-kissy whispering and, when he came back to the table, I was standing up with a guitar and I sang, ‘Pretty woman … don’t need no money’ and then he sang, ‘Pretty woman … walking down the street,'” Dees said. “After that, we both chipped in and within an hour and a half — before she got back to the house — we had it written.”
The guitar riff from “Oh, Pretty Woman” became influential. Wayne Moss, who played guitar on the track, discussed why the riff still resonates. “If you can play a whole bunch of notes in a row, really complicated and real fast, I don’t think it proves as much as playing something you can go down the road humming or whistling,” he said.
"Pretty Woman” became Orbison’s second No. 1 single on the Billboard Hot 100, following “Running Scared.” The former topped the chart for three of its 15 weeks on the chart, making it the singer’s longest-running No. 1 tune. Though Orbison had a distinguished career as a solo artist and as a member of The Traveling Wilburys, he never reached the pinnacle of the chart again.
“Oh, Pretty Woman” appeared on many of Orbison’s compilation albums, including Orbisongs. That album reached No. 136 on the Billboard 200, staying on the chart for a total of 11 weeks.
Cheatsheet
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