Roy Orbison was a bit of an anomaly. In an era where rock stars were supposed to be loud, aggressive, and maybe a little dangerous, here was this guy who looked like a shy librarian. He’d stand perfectly still on stage, hidden behind those iconic thick black sunglasses, and just... sing. But what a voice. It wasn't just a voice; it was a force of nature that could climb four octaves without breaking a sweat.
Honestly, when you look at a list of songs by Roy Orbison, you aren’t just looking at a discography. You're looking at the blueprint for the "vulnerable male" in rock and roll. Before Roy, men didn't really admit to crying. After Roy? It was practically a genre.
The Monument Years: Where the Legend Started
The early 60s were Roy’s playground. After a somewhat clunky start at Sun Records—where Sam Phillips tried to turn him into a rockabilly "shouter" like Elvis—Orbison found his home at Monument Records. This is where the magic happened.
He teamed up with Joe Melson, and together they threw out the rulebook of song structure. Instead of the standard verse-chorus-verse-chorus, they started writing these "crescendo" songs. They’d start quiet, almost like a whisper, and build up into an operatic explosion.
- Only the Lonely (1960): This was the one. Believe it or not, Roy actually tried to give this song to Elvis Presley and the Everly Brothers first. They both turned it down. Their loss was Roy's gain. It hit #2 on the Billboard Hot 100 and basically invented the "Orbison Sound."
- Running Scared (1961): This song is pure anxiety. There’s no chorus. It just keeps building and building over a bolero rhythm until he hits that final, soaring high note. It’s a masterclass in tension.
- Crying (1961): If "Only the Lonely" was the introduction, "Crying" was the thesis statement. It’s probably the most vulnerable song ever recorded by a man in that era. When he hits that final "Crying over you," it’s enough to give you chills sixty years later.
- In Dreams (1963): Roy famously said this song came to him while he was half-asleep. It’s got a weird, shifting structure that shouldn't work on paper, but it’s haunting. David Lynch eventually used it in Blue Velvet, giving it a whole new, slightly creepy life for a younger generation.
The Global Phenomenon of Oh, Pretty Woman
You can't talk about a list of songs by Roy Orbison without spending some time on the big one. In 1964, the "British Invasion" was killing every American artist on the charts. Except for Roy.
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"Oh, Pretty Woman" was a monster. It was inspired by his wife, Claudette, walking into the room and Roy’s songwriting partner, Bill Dees, remarking that a "pretty woman doesn't need any money." The growl, the iconic guitar riff, the "Mercy!"—it all came together perfectly. It stayed at #1 for three weeks and remains one of the most recognizable songs in the history of recorded music.
But life wasn't all hit records. The mid-to-late 60s were brutal for Roy. He lost his wife in a motorcycle accident and then two of his sons in a house fire. His career took a nosedive. He moved to MGM Records, but the hits dried up. For a long time, Roy Orbison was a "heritage act," someone people remembered fondly but didn't expect much from anymore.
The 80s Comeback and The Traveling Wilburys
The 1980s were weirdly kind to 50s and 60s legends, but Roy’s comeback was special. It wasn't just nostalgia; people realized he was still better than everyone else.
He joined the ultimate "dad band" supergroup: The Traveling Wilburys. Imagine being in a band with George Harrison, Bob Dylan, Tom Petty, and Jeff Lynne. Even in that room, Roy was the "Big O." When he sings the bridge in "Handle with Care"—“I’m so tired of being lonely”—it’s like the air leaves the room.
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Notable Late-Career Hits
- You Got It (1989): Released just after his death, this was his first Top 10 hit in 25 years. It’s sunny, catchy, and perfectly produced by Jeff Lynne.
- I Drove All Night (1992): Most people know the Cyndi Lauper version, but Roy’s version (recorded in '87 but released posthumously) is the definitive one. It’s desperate and powerful.
- She’s a Mystery to Me (1989): Written specifically for him by Bono and The Edge of U2. It captures that dark, moody vibe of his early 60s work but with a modern edge.
- California Blue (1989): A beautiful, swaying ballad that proved he never lost his touch for writing about longing.
The Songs You Might Have Missed
If you only know the "Best Of" collections, you’re missing out on some gems.
"Ooby Dooby" is the best of his early rockabilly stuff. It’s silly, it’s fast, and it shows that he could actually "rock" when he wanted to. Then there’s "Blue Bayou." While Linda Ronstadt made it a massive hit in the 70s, Roy’s original version has a certain loneliness to it that she couldn't quite replicate.
And let’s not forget "Claudette." He wrote it for the Everly Brothers (and his wife), and while their version is the famous one, Roy’s own recordings of it are fantastic. It shows his ability to write straightforward, catchy pop-rock before he got into the "operatic" stuff.
What Most People Get Wrong
People often think Roy was just a "sad guy." That’s a bit of a misconception. If you listen to a full list of songs by Roy Orbison, you'll hear plenty of rockers like "Mean Woman Blues" or "Dream Baby (How Long Must I Dream)." He had a great sense of rhythm. He just happened to be the world's best at singing about heartbreak, so that's what stuck.
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Another thing? He wrote or co-wrote almost all of his hits. He wasn't just a "singer" who was handed songs by a studio. He was a craftsman. He knew exactly how to layer strings and backing vocals to make his voice pop.
Practical Steps for Any New Fan
If you're just starting to explore Roy's catalog, don't just stick to the radio hits. Here is how to actually digest his work:
- Start with "A Black and White Night": This 1988 live special is on most streaming services. It features Bruce Springsteen, Elvis Costello, and Tom Waits as his backing band. It’s the best way to see the sheer respect other legends had for him.
- Listen to "Mystery Girl" in full: It was his final album, and it’s arguably his best top-to-bottom record. It doesn't feel like a "comeback" album; it feels like a victory lap.
- Compare the Sun vs. Monument eras: Listen to "Ooby Dooby" and then "Only the Lonely" back-to-back. You can literally hear the moment he finds himself as an artist.
- Check out the Traveling Wilburys Vol. 1: It’s a great way to hear him in a collaborative setting where he’s having fun rather than just carrying the emotional weight of a solo ballad.
Roy Orbison died at just 52 years old, right as he was becoming a superstar all over again. It's a tragedy, sure, but the music he left behind is basically untouchable. Whether you're into rock, country, or just good old-fashioned pop, his songs have a way of getting under your skin. You don't just listen to Roy Orbison; you feel him.