It is a growl that changed music history. You know the one. That purring, hungry sound right before the drums kick back in. If you’ve ever sat through a wedding reception or flipped on a classic rock station, you’ve heard it. But who sang the song pretty woman? While the 1990 movie starring Julia Roberts and Richard Gere made the track a permanent fixture of pop culture for a new generation, the man behind the microphone was the legendary Roy Orbison.
He didn’t just sing it. He lived it.
Orbison, often called "The Big O," wasn't your typical rock star. He wore thick, black sunglasses because of severe astigmatism and a bit of stage fright. He stood still. He didn't gyrate like Elvis. He just stood there and let that three-octave voice do the heavy lifting. "Oh, Pretty Woman," released in 1964, became his magnum opus, but the way it came to be is actually a lot more spontaneous than the polished recording suggests.
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The Afternoon That Changed Everything
Most people assume hits are manufactured in dark rooms by guys in suits. Not this one. The song was born in a living room. Roy Orbison was writing with his partner, Bill Dees, at Roy’s house. Roy's wife, Claudette, walked into the room and mentioned she was headed to town to buy something. Roy asked if she needed any cash.
Dees chimed in with a quip: "A pretty woman never needs any money."
That was the spark. Just a throwaway comment between friends. Orbison immediately started singing, "Pretty woman, walking down the street." By the time Claudette got back from her shopping trip, the song was basically finished. They wrote it in the time it takes to buy a gallon of milk and some eggs. Honestly, that’s how the best ones usually happen. They just fall out of the sky.
The Anatomy of the Riff
The guitar line is unmistakable. It’s a walking riff that builds tension. It starts with just two notes, then four, then the full phrase. It mirrors the act of watching someone walk toward you from a distance. You see a shape, then a face, then the whole person.
Interestingly, there were actually four guitarists on the session at Monument Records in Nashville. You had Roy, Billy Sanford, Jerry Kennedy, and Wayne Moss. They wanted that sound to be thick. They wanted it to drive. If you listen closely, the song isn't just a pop tune; it's a masterpiece of arrangement. It shifts gears constantly. It goes from the aggressive "Mercy!" to the vulnerable "’Cause I need you," and then back to the confident strut.
Why Roy Orbison's Voice Was Different
When you ask who sang the song pretty woman, you’re talking about a guy who Caruso allegedly called the greatest singer in the world. Orbison wasn't a "belter" in the traditional sense. He was an operatic rock singer. He had this incredible ability to start a song in a hushed, almost whispered baritone and end it in a soaring falsetto that could break glass.
In "Oh, Pretty Woman," he stays mostly in his mid-range until the very end. The climax of the song isn't a high note, though. It's the growl. That "Grrrr."
Legend has it that Roy didn't know how to bridge the gap between the verses, so he just made that sound. It was a placeholder that became the hook. It added a layer of grit to a song that could have been too sweet. It made it human. It made it a bit dangerous.
The Van Halen Factor
You can't talk about who sang the song pretty woman without mentioning Van Halen. In 1982, David Lee Roth and the guys decided to cover it. It was a massive hit all over again.
Some purists hated it. They thought the synthesizers and Eddie Van Halen's dirty guitar tone ruined the elegance of the original. But Roy loved it. He actually appreciated that a younger generation was digging his melody. The Van Halen version is faster, louder, and way more "80s," but it proved the bones of the song were indestructible. You could play it on a lute or a heavy metal stack, and that melody would still work.
The Dark Side of the Success
Success is weird. "Oh, Pretty Woman" was a global phenomenon. It was one of the few American records to stay at number one in the UK while the Beatles were dominating the charts. Think about that for a second. The British Invasion was happening, and Roy Orbison was the only guy holding the line.
But shortly after the song peaked, Roy's life took a tragic turn. His wife Claudette—the inspiration for the song—died in a motorcycle accident in 1966. A couple of years after that, two of his sons died in a house fire while he was on tour.
When you hear him sing the song in later years, like in the famous Black and White Night concert film, there’s a different weight to it. He’s still the guy who sang the song pretty woman, but he’s singing it as a man who has lost the woman who inspired it. That’s the nuance of Roy Orbison. His music always had a shadow behind the sunshine.
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The Movie Connection
In 1990, Gary Marshall released a movie called Pretty Woman. You’ve seen it. Everyone has. It turned Julia Roberts into a superstar.
The producers actually had to pay a lot of money to use the song. Originally, they weren't sure if it fit the "vibe" of a movie about a sex worker and a billionaire. But once they edited the shopping montage on Rodeo Drive to Roy’s vocals, they knew they had gold. The song reached a whole new audience. Kids who weren't even born in 1964 were suddenly humming that riff.
It’s one of the few cases where a song and a movie are so inextricably linked that you can’t think of one without the other. Usually, one overshadows the other. Not here. They feed off each other.
Misconceptions About the Title
People often get the name wrong. They call it "Pretty Woman." The official title is actually "Oh, Pretty Woman." Does it matter? Maybe not to most. But if you're looking for the original 45rpm record, that "Oh" is right there on the label. It’s an exclamation. It’s the sound of someone being taken aback by beauty. It’s a small detail, but details are everything in rock and roll.
Other People Who Covered It
While Roy is the definitive answer to who sang the song pretty woman, he’s far from the only one. The list of covers is honestly exhausting.
- Al Green did a soulful, slowed-down version that feels like a late-night fever dream.
- The Beatles used to play it in their early live sets, though they never officially recorded a studio version for an album.
- John Mellencamp has performed it as a tribute.
- Bruce Springsteen famously shared the stage with Roy to sing it, looking like a total fanboy the entire time.
Each version tries to capture that "Mercy!" moment, but nobody quite hits it like Roy. There was a vulnerability in his voice that most rock singers try to hide. He wasn't afraid to sound lonely.
Technical Brilliance in Simplicity
The song is roughly three minutes long. In that time, it manages to tell a complete story with a beginning, middle, and end.
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- The Observation: He sees her.
- The Internal Dialogue: He wonders if she's lonely like him.
- The Rejection: She walks on by.
- The Twist: She turns around and walks back.
That final "Wait... is she walking back to me? Yeah, she's walking back to me!" is one of the most uplifting moments in music. It’s a happy ending that feels earned.
Actionable Insights for Music Lovers
If you want to truly appreciate Roy Orbison's work beyond just "Oh, Pretty Woman," you need to dig a little deeper into the Sun Records and Monument Records catalogs.
- Listen to "In Dreams": This is where you hear his vocal range truly explode. It doesn't follow a standard verse-chorus structure; it just keeps climbing.
- Watch "A Black and White Night": This 1988 concert film features Roy backed by people like Jackson Browne, Tom Waits, Elvis Costello, and Bonnie Raitt. It’s filmed in high-contrast black and white and is arguably the best live performance capture in history.
- Check the Credits: Always look for the name Fred Foster. He was the producer who encouraged Roy to stop trying to sound like Elvis and start sounding like himself.
- Explore the Traveling Wilburys: Before Roy passed away in 1988, he joined a supergroup with Bob Dylan, George Harrison, Tom Petty, and Jeff Lynne. His voice on "Not Alone Any More" will give you chills.
Roy Orbison was a one-off. There will never be another voice like that. When you think about who sang the song pretty woman, don't just think of a catchy tune. Think of a man who took his heartbreak and his glasses and turned them into a sound that will probably be played as long as humans have ears.
To get the full experience, go find the original mono mix of the track. Modern stereo remasters are great, but the mono version has a punch and a center-of-the-room energy that makes the drums sound like they’re right in your face. It's the way it was meant to be heard in a 1964 Chevy Impala with the windows down.