Few voices in music history have the power to stop you in your tracks, and Roy Orbison’s hauntingly beautiful tenor is undoubtedly one of them. Known as “The Big O,” Orbison’s career spanned decades, leaving an indelible mark on rock, pop, and country music. His songs are a masterclass in emotion, weaving tales of heartbreak, longing, and triumph that resonate as deeply today as they did when they first hit the airwaves. Whether it’s his soaring falsetto or his ability to evoke raw vulnerability, Orbison’s music transcends time, offering a universal soundtrack to the human experience.
In this article, we’ll revisit Orbison’s most iconic hits—the songs that not only defined his career but also earned him a place in the pantheon of music legends. From the hypnotic melodies of “Only the Lonely” to the cinematic grandeur of “Crying,” and the electrifying energy of “Oh, Pretty Woman,” these tracks are more than just songs; they’re cultural milestones. So, whether you’re a lifelong fan or new to his genius, prepare to be swept away by the magic of Roy Orbison as we count down the top 10 most popular songs that still captivate hearts around the globe.
1. Oh, Pretty Woman (1964)
“Oh, Pretty Woman” stands as one of Roy Orbison’s most iconic and enduring hits. Released in 1964, the song immediately grabs listeners with its unmistakable guitar riff—catchy, bold, and impossible to forget. Co-written with Bill Dees, it’s a song built around the everyday yet electrifying moment of spotting a beautiful woman walking by. But Orbison transforms that ordinary scene into a powerful blend of desire, admiration, and wonder. His voice, rich and commanding, delivers every line with a mix of confidence and yearning, creating an emotional tension that keeps the listener hooked. There’s a sense of vulnerability under the swagger, as if the speaker isn’t sure if the woman will return his glance or walk away forever. The song’s energy, melodic hooks, and universal theme of infatuation helped propel it to number one around the world, and it remains a staple of classic rock radio. Over the years, “Oh, Pretty Woman” has been covered, parodied, and featured in countless films, most notably in the 1990 movie Pretty Woman, cementing its cultural legacy. It’s a perfect example of Orbison’s talent for mixing rock and roll with emotional storytelling, making it as timeless now as it was in the ’60s.
2. Crying (1961)
“Crying” is one of Roy Orbison’s most emotionally raw and vocally stunning performances. Released in 1961, the song captures the devastation of lost love with poetic sincerity. At first, the narrator claims he’s over it—he’s moved on. But quickly, the façade crumbles, and the truth emerges: he’s still heartbroken, still haunted by memories. Orbison’s voice rises and falls with aching vulnerability, guiding listeners through every layer of sorrow and longing. The orchestral arrangement swells behind him, building to a dramatic crescendo that mirrors the emotional storm he’s experiencing. What makes “Crying” so powerful is its honesty. It doesn’t hide from pain—it embraces it, explores it, and expresses it in a way few songs dare to. Orbison’s vocal range is on full display here, gliding from a trembling whisper to soaring high notes that seem to hang in the air. The song was a huge success, topping charts and earning critical acclaim, and it remains one of his most beloved recordings. Countless artists, from Don McLean to k.d. lang, have covered it, but Orbison’s version remains definitive. “Crying” isn’t just a breakup song—it’s a cathartic release, a heart laid bare, and a true testament to Orbison’s artistry.
3. Only the Lonely (Know the Way I Feel) (1960)
“Only the Lonely (Know the Way I Feel)” was a breakthrough moment for Roy Orbison when it was released in 1960. It marked the beginning of his signature style—melancholic, operatic, and deeply emotional. The song paints a vivid picture of solitude, heartbreak, and the quiet pain that only those who’ve truly been there can understand. From the first haunting notes to the soaring vocal peaks, Orbison makes loneliness sound beautiful, even poetic. Co-written with Joe Melson, and produced by Fred Foster, the song’s lush orchestration gave it a unique sound at the time. It didn’t fit neatly into the rockabilly or pop molds of the day—it was something entirely its own. Orbison’s falsetto and use of dramatic vocal phrasing turned what could’ve been a simple lament into a cinematic experience. The success of “Only the Lonely” launched Orbison into stardom, reaching number two on the Billboard Hot 100 and number one in the UK. It set the stage for the string of emotionally rich ballads that would define his career. More than 60 years later, the song still resonates, a haunting reminder that pain and beauty often go hand in hand.
4. In Dreams (1963)
“In Dreams” is a hauntingly beautiful song that showcases Roy Orbison’s unparalleled storytelling and vocal ability. Released in 1963, the track is far from your typical love ballad—it’s a surreal journey through the subconscious, where love is found, lost, and mourned all within a dream. What sets this song apart is its unconventional structure. It doesn’t follow a standard verse-chorus pattern. Instead, it flows like a short film or a dramatic monologue, growing more intense with each line. Orbison’s vocal delivery is mesmerizing. He begins gently, almost whispering, as he describes finding his beloved in his dreams. But as the dream unravels, his voice builds to a heartbreaking crescendo, filled with longing and pain as he wakes up and realizes it was all just an illusion. The orchestration is delicate yet cinematic, adding to the dreamlike atmosphere. “In Dreams” became a cult favorite and found new life decades later when it was memorably featured in David Lynch’s 1986 film Blue Velvet. That moment introduced the song to a new generation and highlighted its eerie emotional power. “In Dreams” isn’t just a song—it’s a feeling, an experience, and one of Orbison’s most brilliant compositions.
5. Running Scared (1961)
“Running Scared” is a masterclass in musical suspense and emotional drama. Released in 1961, the song unfolds like a psychological thriller, with Roy Orbison as the narrator caught in a tense moment of uncertainty and fear. From the opening notes, there’s a sense of unease—no drums, just a slowly building orchestration that mirrors the narrator’s anxiety. He’s afraid of losing the woman he loves, not knowing if an old flame might take her away. Each verse increases the pressure, drawing the listener deeper into the story. Then, just when the tension becomes almost unbearable, the song explodes into a triumphant final note as the woman chooses him. Orbison delivers the climax with incredible power, his voice soaring in a way that leaves a lasting impact. The song’s structure was groundbreaking at the time—it’s essentially one long crescendo—and it showcases Orbison’s unique ability to blend operatic drama with pop music. “Running Scared” topped the charts and became one of his most celebrated recordings. It’s not just a love song; it’s a cinematic experience packed into under three minutes. With its bold arrangement and emotional punch, “Running Scared” proves why Orbison was a true innovator in popular music.
6. Blue Bayou (1963)
“Blue Bayou” is one of Roy Orbison’s most cherished ballads—a heartfelt ode to longing and the dream of return. Released in 1963, the song showcases Orbison’s gift for painting vivid emotional landscapes through music. With a gentle, swaying rhythm and a melody that feels like a lullaby, the track creates a world where the narrator yearns to go back to a simpler, happier place. “I’m going back someday,” he sings, filled with hope and sadness, imagining a home by the bayou where everything was peaceful and right. Orbison’s voice, rich with nostalgia and ache, breathes life into every line. His delivery is so sincere that listeners can almost see the water, feel the warm sun, and hear the quiet rhythm of life by the bay. The song has a timeless quality, one that’s resonated with generations. Linda Ronstadt’s later cover helped cement its status as a classic, but Orbison’s original version holds a unique magic. It’s a song for anyone who’s ever missed home, dreamed of getting away from the noise, or longed to recapture something lost. “Blue Bayou” reminds us that sometimes the most powerful songs are the ones that speak softly but carry deep emotional weight.
7. It’s Over (1964)
“It’s Over” is a stunning display of heartbreak, drama, and vocal mastery from Roy Orbison. Released in 1964, the song captures the crushing finality of a breakup with raw honesty and theatrical flair. From the first line, there’s no ambiguity—the relationship is done, and the narrator is left to face the silence. What sets “It’s Over” apart is how perfectly the music mirrors the emotional landscape. The orchestral arrangement builds slowly, echoing the rising tension and grief, until Orbison unleashes a vocal performance that’s both powerful and vulnerable. His voice soars into dramatic high notes, trembling with despair, then falls back into hushed sorrow. It’s not just a song—it’s an emotional journey. Each phrase feels like a gasp, a cry, a moment of reckoning. The lyrics are simple, but that’s what makes them effective; they get straight to the point, like a dagger to the heart. “It’s Over” was a major hit in the UK and US, and it remains one of Orbison’s most emotionally resonant tracks. It speaks to anyone who’s had to accept the end of something beautiful, and it proves once again that Orbison was a master at turning pain into unforgettable music.
8. You Got It (1989)
“You Got It” was released in 1989, just months after Roy Orbison’s untimely death, and it feels like a final gift from a legendary artist. Co-written with Jeff Lynne and Tom Petty, the song blends Orbison’s timeless voice with a more modern production, bridging the gap between the 1960s and the late ’80s. It’s uplifting, romantic, and full of genuine warmth. In contrast to many of Orbison’s earlier songs, which explored heartbreak and longing, “You Got It” radiates positivity. It’s a declaration of love, loyalty, and devotion: “Anything you want, you got it.” Orbison sings those words with such sincerity that they feel like a personal promise to the listener. The melody is bright and catchy, with a driving rhythm that gives the track an optimistic energy. Despite being recorded near the end of his life, Orbison sounds as powerful and emotionally expressive as ever. The song became a worldwide hit and introduced his music to a new generation. More than just a chart success, “You Got It” is a reminder of Orbison’s enduring ability to connect through song, no matter the decade. It remains a beautiful testament to the strength of his voice, his spirit, and his legacy.
9. Dream Baby (How Long Must I Dream) (1962)
“Dream Baby (How Long Must I Dream)” is one of Roy Orbison’s more playful and upbeat songs, showing a lighter side to his musical personality. Released in 1962, the track moves away from the dramatic ballads he’s most famous for and embraces a bouncy, rockabilly-inspired rhythm. With a catchy hook and foot-tapping groove, “Dream Baby” feels like a breath of fresh air. The lyrics are simple and fun, centered around the idea of dreaming endlessly about someone you love and wondering when that dream might come true. Orbison’s voice is as smooth and expressive as ever, but here it dances with a kind of joy and excitement that makes the song instantly infectious. The backing band keeps things tight and lively, and the entire song has a radio-friendly charm that helped it become a hit in both the US and the UK. It may not have the emotional weight of “Crying” or “In Dreams,” but “Dream Baby” proves that Orbison could also craft pop songs that are fun, catchy, and full of charm. It’s the kind of track that sticks in your head and lifts your mood—an underrated gem in Orbison’s rich catalog.
10. Mean Woman Blues (1963)
“Mean Woman Blues” is a fiery track that reveals Roy Orbison’s edgier, more rock-driven side. Released in 1963, the song pulses with gritty energy and swagger, a stark contrast to his usual image as the master of melancholy. From the very first chord, you know this is going to be a wild ride. Orbison’s vocals are raw and commanding, capturing the frustration and fascination of being tangled up with a woman who’s as tough as she is irresistible. “She makes me do things I don’t wanna do,” he sings, half warning, half admiring. It’s a bluesy anthem about love gone wild, filled with attitude and emotion. The rhythm is fast-paced and danceable, with a strong backbeat that drives the song forward like a freight train. Orbison leans into the role of the heartbroken rebel, proving he could rock just as hard as any of his contemporaries. “Mean Woman Blues” shows that he wasn’t just a balladeer—he had the grit and soul to handle rough-and-tumble rock and roll, too. It’s a high-energy highlight in his catalog, and a reminder that Orbison’s talent knew no boundaries, whether he was crooning or growling into the mic.
Edward Tomlin is a frequent contributor to Singers Room. Since 2005, Singersroom has been the voice of R&B around the world. Connect with us via social media below.
