The Number Ones

September 26, 1964

The Number Ones: Roy Orbison’s “Oh, Pretty Woman”

Stayed at #1:

3 Weeks

In The Number Ones, I’m reviewing every single #1 single in the history of the Billboard Hot 100, starting with the chart’s beginning, in 1958, and working my way up into the present.


Roy Orbison might be the archetypal sad bastard of pop music. A Sun Records original, he was there for the big-bang birth of rock ‘n’ roll, sharing studio space with the horny young demons who would divide generations. But he wasn’t one of them. He was a goofy-looking potato-faced doof with a magical voice. Orbison didn’t become a commercial force until all those other Sun Records guys had faded, and he did it by tapping into the lost, wounded desperation of the terminally unfucked.

“Crying” and “Only The Lonely” are the distant grandparents of emo and twee. And while “Running Scared” does build up to a climactic happy ending, it’s all tension. You don’t walk away feeling the relief that comes at the end. You remember the overwhelming dread of just knowing that your significant other is about to leave you for someone else. Roy Orbison did not have big dick energy.

So it’s both striking and wonderful that “Oh, Pretty Woman,” which would become Orbison’s biggest hit and signature song, is a flirty, horny romp, one where Orbison really does get the girl at the end and where the stress of not getting the girl never quite plays a factor. In the song, Orbison approaches a girl on the street, and his pick-up lines are all pretty sad and ridiculous. He growls. he grunts, “Mercy!” He asks her, “Are you lonely, just like me?” (No, Roy Orbison. She is not lonely just like you. She is a pretty woman, and you are Roy Orbison.) When she keeps walking, he accepts it with a resigned shrug. And then she comes back anyway. Maybe she liked how he made fun of himself. Or maybe she just liked that riff.

The riff is a world-beater, a twangy and playful little groove. It has to rev itself a little bit to get started, like an old lawnmower. In the session where Orbison recorded it, he had four guitarists playing that riff, maybe to mirror that feeling of growing confidence that you might feel when shit is finally going right. And everything in the song serves the riff, from the urgent opening drum cracks to the way Orbison lets his voice float.

“Oh, Pretty Woman” is a song written from a place of romantic bliss and pure silliness. The story goes that Orbison was sitting down with his songwriting partner Bill Dees when Claudette, Orbison’s wife, came in to tell him that she was going shopping. Orbison asked her if she needed money, and Dees joked that a pretty woman never needs money. By the time Claudette got back from the store, they had the song written.

Y’all like sad stories, right? Here’s a sad story. Roy had married Claudette in 1957, when she was still a teenager. As his star grew and he spent a lot of his time on the road, she started cheating on him. In November of 1964, right as his career should’ve been peaking, Roy learned of Claudette’s affairs, and he divorced her. A little more than a year later, they reconciled and remarried. A few months after that, Roy and Claudette were riding motorcycles together when Claudette crashed into the open door of a pickup truck and died. Two years later, Roy and Claudette’s two oldest sons died in a house fire when Roy was away on tour.

Pop songs, even the happy ones, will fuck around and break your heart.

GRADE: 9/10

BONUS BEATS: Here’s the cartoonish, banned-by-MTV video for Van Halen’s bright, goofy, extremely horny “Oh, Pretty Woman” cover, which got to #12 in 1982:

BONUS BONUS BEATS: 2 Live Crew sampled the “Oh, Pretty Woman” riff on their 1989 lovably stupid quasi-parody “Pretty Woman.” Orbison was dead by then, but Acuff-Rose, his publisher, sued. 2 Live Crew claimed that it was a parody and that it was protected under fair-use laws. The case made it to the Supreme Court, which, in a decision that I can’t imagine happening today, ruled in favor of 2 Live Crew. Here’s the 2 Live Crew song:

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