62 Years Ago Today, Roy Orbison Released the No. 1 Classic Born From a Songwriter’s Offhand Remark About His Wife

August 29, 2026, 3:33pm

During a time when swagger and bravado were especially desirable attributes for male performers, Roy Orbison dared to let vulnerability take center stage. With his dyed black hair, dark sunglasses, and all-black ensemble, the Texas-born star knew how to pull on listeners’ heartstrings on songs like “Only the Lonely” and “Running Scared”.

With that said, “Oh, Pretty Woman” — released on this day (August 29) in 1964 — took a hard left turn. It’s a purely frivolous response to a lady’s external beauty, and it’s virtually impossible not to groove along to: Pretty woman / I don’t believe you, you’re not the truth / No one could look as good as you.

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Quoting Bruce Springsteen, Orbison’s second wife, Barbara, dubbed it “the best girl-watching rock ‘n’ roll song ever” in a 2008 interview with NPR.

Selling a staggering seven million copies, “Oh, Pretty Woman” topped the U.S. pop chart for three weeks, giving Orbison his second and final number-one hit on that listing after “Running Scared”.

It also marked his third chart-topper in the United Kingdom and reached number one in multiple other countries — including Australia, Belgium, Canada, Hong Kong, Ireland, the Netherlands, New Zealand, Norway, Singapore, Switzerland, and West Germany.

Roy Orbison was just 52 years old when he unexpectedly died of a heart attack on December 6, 1988. Nearly 40 years later, “Oh, Pretty Woman” still stands out in a catalog full of gems.

Roy Orbison Wrote This Song for His First Wife

The defining hit of Roy Orbison’s career began with a simple trip to the store. His wife, Claudette, informed him that she was leaving the house.

When Orbison asked her if she had enough cash, his co-writer, Bill Dees, interjected, “A pretty woman never needs any money.”

That led to Orbison singing, Pretty woman, walking down the street. By the time Claudette returned home, the two men had written “Oh, Pretty Woman”.

“He sang it while I was banging my hand down on the table and by the time she returned we had the song,” Dees later recalled, per Songfacts. “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.

“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.”

It Preceded a Personal Unraveling

Roy Orbison wrote “Oh, Pretty Woman” during a period of reconciliation with his wife, Claudette, after spending some time apart.

Once the song hit the charts, however, Orbison learned she was cheating on him with the carpenter who’d built his home. He filed for divorce, but the separation was brief — they remarried in 1965.

Tragically, their reunion was also fleeting. On June 6, 1966, Claudette died in a motorcycle accident near Gallatin, Tennessee. She was just 25 years old.

His wife’s untimely death was the first in a chain of personal tragedies that derailed Orbison’s career in the 1970s. Just two years later, in 1968, his two young sons died in a fire at the singer’s home in Hendersonville, Tennessee.

Orbison would bounce back in the 1980s, forming iconic supergroup the Traveling Wilburys with some little-known artists named Bob Dylan, George Harrison, Jeff Lynne, and Tom Petty.