Fifty years ago Monument Records would release the track that would become the most celebrated single in the career of Roy Orbison, one of the most revered songwriters and rock 'n' rollers in American history. "Oh, Pretty Woman" (often incorrectly titled as simply "Pretty Woman") would ensure that Orbison's name was remembered, even if the catalogues of fellow Sun Records members Elvis Presley and Johnny Cash got most of the attention.
Naturally a song as iconic as "Oh, Pretty Woman" has seen its fair share of covers over the years.
06) "Oh, Pretty Woman" by Alvin and The Chipmunks (1990)
Let's be upfront with our bias: We hate the Chipmunks and every cover from this animated group will be placed last in every list we ever write. If it's not "Christmas Don't Be Late" we don't want to hear it. Nearly 30 years after brutalizing The Beatles on a covers album, the Chipmunks are still at it, torturing poor Orbison's classic with their obnoxious voices. What's sad is that this track from Rockin' Through The Decades was one of the better numbers...the hip-hop interpretations were just nightmares.
05) "Oh, Pretty Woman" by Johnny Rivers (1964)
The '50s and '60s was an era when you could take a song that was popular last year, rebrand it and turn it into a hit. Johnny Rivers wasn't trying to do this in 1964, literally the same year that Orbison's version came out, but his live album In Action was chock full of covers. The Beatles, Chuck Berry, Pat Boone, Bobby Womack and Sam Cooke are just a short list of acts that Rivers copped a hit from for his performance. Unfortunately he didn't do much to spruce up Orbison's original so this really isn't worth the time.
04) "Oh, Pretty Woman" by Johnny Cougar (1976)
Does that performer's name sound familiar? Yes, of course it's an early version of who we know now as John Cougar Mellencamp. Before he became huge with tracks such as "Jack and Diane," the songwriter didn't do much songwriting at all. In fact, his '76 album The Chestnut Street Incident was itself a huge collection of covers, except not a live album such as was Rivers' case. Another fairly straightforward cover, albeit not as misjudged as his takes on The Doors and The Stooges from the same album.
03) "(Oh) Pretty Woman" by Van Halen (1982)
For some odd reason Van Halen was also in the mood to go cover crazy around the release of Diver Down. This had all the potential in the world...even if it wasn't good, at least we should have been assured of something different. Tack on a monumental solo from Eddie Van Halen, or transform Orbison's lonesome moans into hypersexual David Lee Roth howls. Unfortunately none of the above happened. If there's any reason to check this track out, it's for the absurd music video.
02) "Oh, Pretty Woman" by the Holy Sisters of The Gaga Dada (1986)
The most interesting cover of Orbison's classic certainly comes from the most interesting band on the list. First there's the fact that the song is sung by women...somewhat ironic. And then there's everything else. The song is recognizable from the opening walking bassline but everything else is off-kilter, from synth-strikes to Far Eastern themes, to the rapid pace at which vocalist Mary Jean carries the lyrics. This version will appall hardcore fans of the original but at least they get points for coloring outside the lines.
01) "Oh, Pretty Woman" by Al Green (1972)
It might not seem that obvious from first take: Rock 'n' roll legend Roy Orbison and soul legend Al Green. But rock was a lot more soulful than it is now, and that aforementioned bassline from the originals sets a mighty fine framework for a performer such as Green to convert it into an R&B hit. The key difference is tone (see what we did there?): Orbison is too worried about whether he can even get such a woman and Green just knows. A dramatically different product without changing all that much.