THE HIT HAMMER: Roy Orbison's "Oh, Pretty Woman"
- Ryan Paris
- Feb 16, 2020
- 4 min read

(The Hit Hammer is where I'm reviewing each #1 song on the Billboard Hot 100. Starting from when the chart started in 1958 and eventually working my way to the present. To see my inspiration and more information about this blog, please refer to the "Poor Little Fool" post)
Roy Orbison - "Oh, Pretty Woman"
Hit Number 1: September 26, 1964
Stay at Number 1: 3 Weeks
There isn't any sugarcoating it, the Beatles might have derailed a lot of careers. Only a handful of artists were still relevant after the British Invasion, with artists like the Beach Boys and the Four Seasons still making the charts before and after the arrival of the different British acts. And to their credit, they are some of the best acts to ever make music, so it isn't any surprise that they "survived" the British Invasion. Among those legendary acts, is none other than Roy Orbison, that guy with the quiver of a voice and the iconic dark shades. He appeared in this blog once before with the power ballad "Running Scared" in 1961, and he rose to #1 again in 1964, surrounded by British rockers. How could this have happened? Maybe a good deal of that can be chalked up to the fact that his second #1 "Oh, Pretty Woman" is pretty different from "Running Scared", as it rocks out a little bit harder.
The whole idea of the song came from one night where Orbison's wife, Claudette, proclaimed that she was going out. After Orbison asked her if she had any money, his co-writer Bill Dees chimed in "A pretty woman never needs any money". Now if it were me, that would really concern me as a husband, but for Orbison, it inspired his most well-known and biggest hit. The song is about a lonely guy who spots a pretty woman out in public, and he can't help but wonder if just maybe, she's lonely just like he is. He desperately wants the woman to stop and "talk awhile" with him, but it looks like she is going to walk right past him. However at the last possible moment, she turns around and walks back in his direction. Of course, the song never specifies that she's going back for HIM. Maybe she saw someone she knew, or she forgot something where she came from, but since the song is obviously hinting she IS going back for the narrator, we'll go with that. Besides, who doesn't like a happy ending?
While "Oh, Pretty Woman" is not a banger of any kind, it still finds a way to slap hard. The song doesn't waste any time to get going, starting out with loud drum beats, and that immortal guitar riff sprinkling over it, before finally Orbison joins in with "Pretty woman, walking down the street", and then the song moves in a steady pace for the rest of it. The song doesn't rock your socks off, it just smoothly glides along, never in any rush. Part of that is probably because this is one of those songs that wants you to pay attention to the lyrics. It's telling a story, and you want the girl to just turn this guy's way. It's kind of like watching a movie and you want the good guys to get what they want. Orbison's character in this song is the good guy, and we can assume that he got his wish at the end of the song.
Like I said, the song isn't going to make you get up and move. (It might have some potential to do that I guess) However, this song is the most iconic moment of Orbison's career, and it truly is his second masterpiece along with "Crying". (a 10 of course) You get what you get with any Orbison song: His quiver of a voice and overall sincerity and innocence in his songs. But there's something different about "Oh, Pretty Woman". It jumps out at you more than his other songs, it COMMANDS you to listen. The song's drums to open up the song won't allow you to ignore it. And that's why I like it so much. Not to mention, it was the brightest spot of a well-established music career.
Unfortunately, tragedy would strike Orbison's life on more than one occasion after the success of "Oh, Pretty Woman". Him and his wife Claudette, who inspired the song, divorced but eventually reconciled after only 10 months. But Orbison's career was beginning to decline a little due to the British Invasion, despite being successful for the first part of it. Life got as worse as it possibly could from there on out. Just a few months after him and his wife remarried, the two had a growing interest in motorcycles, which they would begin to ride regularly. On their way home from Bristol, Tennessee, Claudette struck the door of a pickup truck which pulled out in front of her and died instantly. This obviously messed him up pretty bad. A couple years later, when he was on tour in England, he received news that his two eldest sons died in a house fire. Imagine losing your wife, two of your children, and your home in a span of just 3 years. If you think your life sucks, just look at what this man had to go through.
Life did get a little better for Orbison as the years went on. He remarried in 1969, and in the 1980s, got his music career back on the map again after joining the supergroup the Traveling Wilburys with Tom Petty, Bob Dylan, George Harrison, and E.L.O. lead singer Jeff Lynne. (Surprisingly, Harrison is the only one of this group that will appear in this blog again in any way shape or form) Orbison died in 1988 of a heart attack, a day after eating dinner at his mother's home. He lived a life of fame, but also one filled with tragedy. But no other song defines his musical career quite like "Oh, Pretty Woman".
GRADE: 10/10
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