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The Story Behind the Song "(Oh), Pretty Woman" by Roy Orbison

Rockin’ before she could walk, Kaili is a vinyl hound who knows the words to every post-1960 song.

Roy Orbison in 1965.

Roy Orbison in 1965.

Roy Orbison began his professional career singing rockabilly and country tunes in the 1950s. His vocal range spanned almost four octaves, and his powerful delivery and falsetto became a musical signature for him and made his songs instantly recognizable.

(Roy Orbison is) quite simply, the greatest singer in the world.

— Elvis Presley at Orbison's Caesar's Palace show, December 1976

Who Is Roy Orbison?

Born in Vernon, Texas on April 23, 1936, Orbison's father gave him a guitar when he was six years old, and from that moment on, he somehow knew that he would devote his life to music. He actually began singing on a local radio show when he was only eight years old, a testament to his talent even at that tender age.

The Wink Westerners

It was in high school that things really began to come together for Orbison musically. He and a few friends formed The Wink Westerners, a band named after their Wink, Texas, hometown.

The group performed all of the country music standards of the day, and they were talented enough to land a spot on a weekly radio show out of Kermit, Texas. That show led to the group being offered the princely sum of $400 to play at a dance, and Orbison was more convinced than ever that music was for him.

Elvis Presley Changes the Game

After a year of studying at North Texas State College in Denton, Orbison switched to Odessa Junior College. It was in Odessa that he first saw a performance by Elvis Presley.

On April 16, 1955, Orbison caught Presley’s act at the Sportatorium. Orbison was shocked at what he considered to be Elvis's gaudy appearance and the way the girls in the audience reacted to the singer. But, the music ultimately won him over.

Johnny Cash and Sun Records

In 1956, Johnny Cash's tour made a stop in Odessa and he appeared on the same television show as Wink Westerners. Cash was impressed with the group and suggested that they contact Sam Phillips, who was the head of Cash's label, Sun Records.

"Ooby Dooby"

Orbison reached out to Sam and was turned down, with Sam telling him that Cash didn't run Sun Records. Not long after this, a local record dealer named Cecil “Poppa” Hollifield called up Sam and played a demo record of Orbison singing “Ooby Dooby” over the phone.

Orbison's group—now known as the Teen Kings—were in Memphis three days later to re-record “Ooby Dooby” Sam's way.

Roy Leaves Sun

Orbison became discouraged after a brief time at Sun Records. While the song “Ooby Dooby” spent eight weeks on Billboard’s Top 100 pop chart and peaked at #59 in the summer of 1956, tours to promote the record saw Orbison mostly doing other people's songs.

Orbison had also disagreed with Sam over the release of songs that Orbison didn't feel were good enough, so he quit. He kicked around Texas for several months, writing songs when he wasn't performing.

Monument Records

Orbison ended up in Nashville, signing on to the fledgling label Monument and joining a group of session musicians known as "The Nashville A-Team."

Orbison's first release on Monument, the song "Uptown," only got to #72 on the Billboard Top 100, but the sound was so different, it was clear that Orbison was about to have a breakthrough.

"Only the Lonely"

That breakthrough came in 1960 on his next release on Monument, with the song "Only the Lonely (Know the Way I Feel)," featuring that wonderful falsetto that became Orbison's signature sound.

More hits followed in 1961, with "Running Scared" and "Crying" both reaching the top of the charts. "Dream Baby" followed in 1962, "Blue Bayou" in 1963, and "It's Over" in April 1964.

Monument Records released "(Oh), Pretty Woman" as a single in August 1964 and it spent three weeks at number one!

Monument Records released "(Oh), Pretty Woman" as a single in August 1964 and it spent three weeks at number one!

Writing "(Oh), Pretty Woman"

Orbison and his songwriting partner Bill Dees were busy writing songs at Orbison's home when Orbison's wife Claudette came in and said she was going in to town to do some shopping.

Orbison asked Claudette if she needed any money, and Dees remarked that "Pretty woman never needs any money." Inspired by that wisecrack, Orbison came out with the line, "Pretty woman, walking down the street." Dees picked up on that line, rapping his fingers on the table, mimicking the rhythm of a woman's high heels on pavement.

Roy's Final #1

They had the song written by the time Claudette returned, and Orbison recorded it the following week. The single was released in August 1964 and spent three weeks in the #1 spot. It was his final song to reach the number one spot on the Billboard Top 100 chart.

Roy Suffers Multiple Losses

Though Orbison continued to record music, his career began to wane with the arrival of the British Invasion in the mid-1960s. The man lauded by fellow musicians like Jerry Lee Lewis and Elvis was no longer a hit-maker.

He made a move to the MGM label in 1965 and released 11 albums with them, the last one being 1973's Milestones. Only the very earliest of those LPs even made the charts.

He followed up with a single LP for Mercury records in 1975, and then made a return to the Monument label in 1976. But, the magic was gone. He released his last LP of new material in his lifetime on Asylum Records in 1979.

Death of Wife and Sons

As if his waning career wasn't enough, Orbison's personal life saw tragedy as well. Claudette, who he had divorced and remarried, died in a motorcycle accident in June 1966.

And in September 1968, his two eldest sons perished when the family home burned down. Health-wise, Orbison had never been a very robust man, and in 1978 he underwent triple-bypass surgery. A lifetime of smoking had taken its toll.

Van Halen Records "(Oh), Pretty Woman"

One of the releases that helped return Orbison's name into the collective consciousness was Van Halen's 1982 cover of "(Oh), Pretty Woman." The band's plan was to release the single and then take a much-needed break from recording and touring.

Unfortunately for the band, the song was a hit, and the record company started pressuring them to get back to the studio to do another album. They did, and their fifth studio album Diver Down, which included the song, was finished in just two weeks.

Diver Down

Though he struggled to release another hit record of his own, other artists who loved Orbison's music were busy hitting the charts with covers of songs like "Love Hurts" (Nazareth, 1975), "Dream Baby," "Blue Bayou" and "Crying."

In 1981, Orbison finally won his first Grammy Award for a duet with Emmylou Harris on "That Lovin' You Feelin' Again."

Rock and Roll Hall of Fame

He continued to collaborate on different projects through the '80s, and in 1987 Orbison was inducted into both the Nashville Songwriters Hall of Fame and the Rock and Roll Hall of Fame, with Bruce Springsteen making the induction speech at the latter event.

Orbison's Velvety Comeback

Roy's career received a boost from an unlikely source. In September 1986, David Lynch released arguably the most popular film of his career. Blue Velvet was like a bizarro version of a 1950s Douglas Sirk movie, and its most memorable sequence featured Dean Stockwell lip syncing to Roy Orbison's brilliant mini-opera, "In Dreams."

A Black and White Night

Orbison was riding high by the time he and Springsteen teamed up for "Roy Orbison and Friends: A Black and White Night," recorded on September 30, 1987. Having watched this special many times, I highly recommend it.

Filmed entirely in black and white, it features guests including Bruce Springsteen, Elvis Costello, k.d. Lang and Bonnie Raitt.

So many people lent a hand in making this wonderful concert, and it is clear when you watch it how much these guests—all big names in their own right—loved Orbison and his music.

Traveling Wilburys

More great collaborative work followed in 1988 with the formation of the Traveling Wilburys, a group consisting of Orbison, George Harrison, Bob Dylan, Tom Petty and Jeff Lynne.

Sadly, Orbison's return to stardom was cut short when he died of a heart attack on December 6, 1988, at the age of 52.


Roy minded his own business, stayed in his place … he might come by just to say hello, hug your neck real nice, and get out of your hair. He was that kind of person. He was a pretty nice guy, wasn’t he?

— Jerry Lee Lewis, upon hearing about Roy Orbison's death

Five Roy Facts

  1. While signed to the Sun label, Orbison began hanging out with Elvis. The two, though they were musical adversaries, were good friends, and Orbison became one of Elvis's trusted inner circle. When Elvis died, Orbison said "I know Elvis had a strong faith, but it was just that there was no one close enough to him, that loved him enough, to tell him what he was doing to himself."
  2. Orbison figured he needed to project a certain image if he was going to be part of Elvis's entourage, so he spent his first royalty check from Sun on a Cadillac and a diamond ring. After an upgrade to both the car and the ring, Orbison realized that trying to keep up with Elvis was futile, so he stopped.
  3. One of Orbison's nicknames was "The Big O." He was also called "The Caruso of Rock" after the Italian tenor Enrico Caruso, who is still widely regarded as being the greatest tenor of the 20th century. Caruso and Orbison had something in common—both tenors, they were able to hit the musical note of E over high C. That's where Orbison's fabulous falsetto came from.
  4. In 1964, Orbison was the only American artist with a #1 hit in the UK, and he managed it twice that year, with "(Oh) Pretty Woman" and "It's Over."
  5. The use of "mercy" in the song actually came from Bill Dees, who said he couldn't do the growl like Orbison, but the expression itself was one he used regularly.

© 2022 Kaili Bisson