The Most Memorable ‘Pretty Woman’ Covers Ever Recorded

Some hits arrive after months of painstaking work. Roy Orbison’s “Oh, Pretty Woman” arrived almost by accident.

Orbison was at home writing with longtime collaborator Bill Dees when the spark struck. As the story goes, Orbison’s first wife, Claudette, walked through the room on her way out to do some shopping. Orbison casually asked if she needed cash, prompting Dees to fire off a quick joke: “A pretty woman never needs any money.”

It was a throwaway line, but the writers recognized its potential instantly. By the end of the day, they had shaped it into a fully formed song that would soon become one of the most recognizable singles of the rock era.

“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,” Dees later recalled in the 2005 book 1000 UK Number One Hits.

Orbison recorded the track on Aug. 1, 1964. Just two weeks later, on Aug. 15, it hit the shelves and quickly soared to No. 1 on the Billboard Hot 100, where it stayed for three consecutive weeks. Nearly three decades later, in 1991, “Pretty Woman” earned Orbison a posthumous Grammy Award for Best Male Pop Vocal Performance—proof of its enduring appeal.

While the original remains untouchable, many artists have stepped up to reinterpret the song in their own style. Here are six notable versions worth revisiting—or discovering for the first time.

1. Van Halen
Perhaps the most widely recognized cover comes from Van Halen, who recorded “Pretty Woman” for their 1982 album Diver Down. Producer Ted Templeman admitted he fought the idea from the start. “I never wanted them to do that song. I didn’t like it, even when Roy Orbison did it,” he wrote in Ted Templeman: A Platinum Producer’s Life in Music. “If they wanted to redo an oldie, I could’ve thought of 10 better song ideas… It still sounds wrong for them to me, but they’d settled on it.”

His skepticism didn’t matter. The single reached No. 12 on the Billboard Hot 100 and became one of the band’s most recognizable MTV-era moments.

2. Al Green
Al Green slipped his silky interpretation of “Pretty Woman” onto his 1972 album I’m Still in Love With You, a record already stacked with major hits. While not released as a single, his version is a masterclass in phrasing—Green bends the melody into something distinctly his own, proving how comfortably Orbison’s songwriting adapts to soul.

3. The Ventures
Leave it to The Ventures to ask: What if “Pretty Woman” were a surf-rock instrumental? Their 1965 take on Knock Me Out! answers the question with twangy guitars, tight rhythms, and an aesthetic that lands somewhere between California beaches and teenage garage jams. It’s a reminder of the song’s melodic simplicity—and resilience.

4. John Mellencamp (as Johnny Cougar)
Before he shed the stage name “Johnny Cougar,” John Mellencamp included a cover of “Pretty Woman” on his 1976 debut, Chestnut Street Incident. His admiration for Orbison goes back to childhood. “When I was a kid, my parents had a Roy Orbison record,” he once recalled. “When I heard him sing, I asked them if they thought there was a special device that was used to make him sound like that… He sang so beautifully I just had to ask.”

Mellencamp’s version doesn’t try to out-sing Orbison—few could, but it reveals the early roots of an artist still discovering his voice.

5. Del Shannon
Del Shannon brought his signature energy to his 1966 studio recording on This Is My Bag. But the real gem came years later: a 1989 live mashup intertwining “Pretty Woman” with the Rolling Stones’ “(I Can’t Get No) Satisfaction.” The performance shows Shannon’s ability to fuse eras and styles while tipping his hat to Orbison, a close friend and fellow architect of early rock.

6. Bruce Springsteen & John Fogerty
Bruce Springsteen inducted Orbison into the Rock & Roll Hall of Fame in 1987, offering one of the most heartfelt tributes in the institution’s history. “He had the ability, like all great rock and rollers,” Springsteen said, “to sound like he dropped in from another planet and yet get the stuff that was right to the heart of what you were living in today.”

He went on to admit that when recording Born to Run in 1975, he wanted the words of Dylan, the sound of Phil Spector—and “most of all, I wanted to sing like Roy Orbison. Now, everybody knows that nobody sings like Roy Orbison.”

More than twenty years later, Springsteen joined forces with John Fogerty for a live performance of “Pretty Woman” at Madison Square Garden, a collaboration that felt like a rare cross-generational salute to a titan who influenced them both. Their version wasn’t about reinventing the song; it was about honoring its spirit—two American rock icons reveling in Orbison’s legacy in front of a crowd that understood exactly why the song still matters.