The Story Behind Roy Orbison’s Repeat Hit “Oh, Pretty Woman”

Playing through some songs at home one day working with songwriter and collaborator Bill Dees, Roy Orbison noticed his wife Claudette Frady getting ready to go out to buy something in town. When Orbison asked her if she needed any money, Dees interjected “Pretty woman never needs any money.” Inspired by Dees’ quip, Orbison started singing Pretty woman walking down the street.

“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.”

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[RELATED: 7 Songs You Didn’t Know Roy Orbison Wrote for Other Artists]

“Oh, Pretty Woman”

Released on August 15, 1964, “Oh, Pretty Woman” went to No. 1 internationally, including on the Billboard Hot 100.

Pretty woman walkin’ down the street
Pretty woman, the kind I’d like to meet
Pretty woman, I don’t believe you, you’re not the truth
No one could look as good as you


Mercy


Pretty woman, won’t you pardon me?
Pretty woman, I couldn’t help but see
Pretty woman, that you look lovely as can be
Are you lonely just like me?


“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,” Orbison told NME in 1980. “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.”

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American singer, guitarist, and musician Roy Orbison (1936-1988) performed on the ‘Thank Your Lucky Stars’ television show for ABC Weekend Television at Alpha Studios in Aston, Birmingham England in February 1965. (Photo by David Redfern/Redferns)

‘Mercy’ and the Growl

In the middle of the song, Orbison lets out a growl, something that was completely improvised, and kept in the song, while his earlier yell of Mercy was inspired by something Dees would often say. “I can’t do that growl like Roy, but the ‘Mercy’ is mine,” said Dees. “I used to say that all the time when I saw a pretty woman or had some good food—still do.”

(Orbison’s Growl)

Pretty woman, stop awhile
Pretty woman, talk awhile
Pretty woman, give your smile to me
Pretty woman, yeah, yeah, yeah
Pretty woman, look my way
Pretty woman, say you’ll stay with me
‘Cause I need you, I’ll treat you right
Come with me, baby, be mine tonight


Pretty woman, don’t walk on by
Pretty woman, don’t make me cry
Pretty woman, don’t walk away, hey
Okay
If that’s the way it must be, okay

I guess I’ll go on home, it’s late
There’ll be tomorrow night, but wait
What do I see?
Is she walkin’ back to me?
Yeah, she’s walkin’ back to me
Oh, oh, pretty woman

“He turned to me with the guitar lick, and he said, ‘I feel like I need to say something while they’re playing [that guitar lick],’” Dees added in a 2008 interview. “I said, ‘Well, you’re always saying [the word] ‘mercy,’ why don’t you say mercy?’ You know, I said, ‘Every time you see a pretty girl you say mercy.’”

[RELATED: The Hit Roy Orbison Originally Offered to Elvis Presley and the Everly Brothers]

Van Halen and ‘Pretty Woman’

In the early ’80s, “Oh, Pretty Woman” started had a small resurgence when Van Halen covered the song on their fifth album Diver Down. By the late ’80s, Orbison had already joined the Traveling Wilburys and, after a slump for some years, was experiencing a comeback in his career, shortly before his death in 1988 from a heart attack at age 52.

Just two years after his death, “Oh, Pretty Woman” circled back around, inspiring the title of Garry Marshall’s romantic comedy starring Julia Roberts and Richard Gere. Featured in the film Pretty Woman, Orbison’s classic hit made the charts again, peaking at No. 12.

A year later, Orbison won a posthumous Grammy for Best Male Pop Vocal Performance for the live version of “Oh, Pretty Woman” from the 1988 TV special Roy Orbison And Friends: A Black And White Night.
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When “Oh, Pretty Woman” was written, Orbson and his wife had reunited after some time apart. When the song hit the charts, Orbison learned that she was cheating on him and filed for divorce.

In 1966, they remarried again but Frady died in a motorcycle accident, two months after they got back together.

Photo: Roy Orbison (1936-1988), circa 1958. (Evening Standard/Getty Images)

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