Six Rockin’ Covers of Roy Orbison’s ‘Pretty Woman’

Roy Orbison’s “Oh, Pretty Woman” came about effortlessly.

At home one day, working on some songs with cowriter Bill Dees, Orbison’s first wife, Claudette, passed through the room, announcing that she was on her way out for some shopping. Orbison asked her if she needed any money, but Dees swiftly interjected: “A pretty woman never needs any money.”

It was a bit of a joke, but the two men rolled with the idea and before the day was out, they had a whole new 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,” Dees said for the the 2005 book 1000 UK Number One Hits.

The song was recorded on Aug. 1, 1964 and released exactly two weeks later on Aug. 15 where it went to No. 1 on the Billboard Hot 100 and stayed there for three weeks. Nearly 30 years after that in 1991, “Pretty Woman” earned Orbison a posthumous Grammy Award for Best Male Pop Vocal Performance.

There’s no topping the original, but below are six other versions of the song that are worthy of checking out.

1. Van Halen

We simply must start with probably the most famous cover of “Pretty Woman,” which was recorded by Van Halen for their 1982 album Diver Down. Interestingly, the band’s producer, Ted Templeman, was not on board with the idea at all. “I never wanted them to do that song. I didn’t like it, even when Roy Orbison did it,” he wrote in his autobiography 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. So at the time I thought it was totally wrong for Dave [Roth] as a vocalist and Van Halen as a band. It still sounds wrong for them to me, but they’d settled on it.” Things turned out just fine though — the single went to No. 12 on the Billboard Hot 100.

2. Al Green

Al Green’s 1972 album I’m Still in Love With You contained several hit songs, including the title track and “Look What You Done for Me.” Plus, the album itself went to No. 4. But we’d encourage listeners not to skip over his cover of “Pretty Woman,” which fits Green’s vocal style so well.

3. The Ventures

What if “Pretty Woman” was a surf rock instrumental? Wonder no more, because the Ventures did exactly that for their 1965 album Knock Me Out! 

4. John Mellencamp

Technically speaking, this cover is by Johnny Cougar, before that name was shed by John Mellencamp. His rendition of “Pretty Woman” appeared on Mellencamp’s debut album, Chestnut Street Incident, in 1976. “When I was a kid, my parents had a Roy Orbison record in their collection,” Mellencamp 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, and they said they didn’t think so. He sang so beautifully I just had to ask.”

5. Del Shannon

When you are done listening to Del Shannon’s 1966 studio version of “Pretty Woman,” from the album This Is My Bag, we recommend following it up with watching the live mashup of “Pretty Woman” and the Rolling Stones’ “(I Can’t Get No) Satisfaction” that he did in 1989.

6. Bruce Springsteen and John Fogerty

Back in 1987, it was Bruce Springsteen who inducted Orbison into the Rock & Roll Hall of Fame. “He had the ability, like all great rock and rollers,” the Boss said then, “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, and it was how he opened up your vision. … In 1975, when I went into the studio to record, Born to Run, I wanted to make a record with words like Bob Dylan, that sounded like Phil Spector’s productions, but most of all I wanted to sing like Roy Orbison. Now, everybody knows that nobody sings like Roy Orbison.” A little over 20 years later, Springsteen joined forces with John Fogerty for a live version of “Pretty Woman” at New York City’s Madison Square Garden.

Bonus: The Chipmunks

We could not resist throwing in this silly surprise at the end. Yes, the Chipmunks once covered “Pretty Woman” for their album Rockin’ Through the Decades.