Roy Orbison, the legendary voice of the ’60s, captivated millions with his haunting melodies and emotional storytelling. Known for his distinctive sunglasses and powerful, operatic voice, Orbison crafted a unique sound that transcended genres and generations. From heart-wrenching ballads to upbeat rock ‘n’ roll hits, his music resonates with listeners, evoking nostalgia and passion.
In this article, we delve into the top 10 most popular Roy Orbison songs of all time, exploring the tracks that defined his illustrious career and solidified his status as a musical icon. Each song tells a story, painting vivid pictures of love, loss, and longing, showcasing Orbison’s genius as a songwriter and performer.
Whether you’re a lifelong fan or new to his music, this countdown promises to take you on an emotional journey through Orbison’s best work. So, grab your headphones and prepare to be swept away by the timeless magic of Roy Orbison, as we celebrate the songs that continue to echo through the halls of music history. Join us as we reminisce about the unforgettable moments captured in his most beloved tracks!
1. “Oh, Pretty Woman” (1964)
Released in 1964, “Oh, Pretty Woman” became one of Roy Orbison’s most iconic songs—and for good reason. Its unforgettable guitar riff and Orbison’s commanding vocals immediately hook the listener. The lyrics capture a moment of admiration as the singer watches a beautiful woman walk by, imagining a connection that might blossom from a fleeting glance. But beyond the surface-level catchiness, the song carries a subtle vulnerability, as Orbison balances confidence with self-doubt. His delivery makes it feel both grand and personal at the same time. The chorus—“Pretty woman, walkin’ down the street”—has become a cultural touchstone, referenced and covered endlessly. It topped the charts across the globe and helped cement Orbison’s legacy in pop and rock history. Its success lies not just in the melody, but in the emotion Orbison conveys so naturally. The song manages to be playful and sincere, bold and romantic. Decades later, it still resonates with listeners of all ages, remaining a staple in film, commercials, and classic rock radio. “Oh, Pretty Woman” isn’t just a hit—it’s a lasting symbol of admiration, heartache, and the hope that love might be just around the corner.
2. “Only the Lonely” (1960)
“Only the Lonely” marked a turning point in Roy Orbison’s career and in the world of emotional pop ballads. Released in 1960, the song revealed the depths of Orbison’s expressive voice and established the signature sound that would define his legacy. With its aching lyrics and haunting orchestration, it tells the story of heartache that many listeners could relate to—feeling isolated in love, watching others happy while you suffer in silence. Orbison’s soaring vocals tap into a universal sadness, making each word feel deeply personal. The layered harmonies and sweeping string sections give the track a cinematic quality that set it apart from typical pop fare of the time. It reached the top of the charts and announced Orbison as a new kind of star—one who wasn’t afraid to show emotional vulnerability in a genre dominated by bravado. More than sixty years later, “Only the Lonely” still holds its power, not only as a beautiful song but as a cultural artifact that redefined how heartbreak could sound in popular music. It remains a haunting anthem for anyone who has ever loved and lost.
3. “Crying” (1961)
Roy Orbison’s 1961 hit “Crying” is one of the most emotionally raw performances ever recorded. From the very first note, Orbison pulls listeners into a world of overwhelming sorrow and heartbreak. The song begins with restraint, almost conversational, but gradually builds into an outpouring of emotion, culminating in Orbison’s powerful, trembling delivery of the word “crying.” What makes the song so compelling is how it mirrors the emotional stages of grief—initial composure giving way to honest vulnerability. The lush string arrangement and echoing background vocals serve as a perfect backdrop for the emotional climax. Orbison’s voice effortlessly glides between octaves, embodying the heartbreak he’s describing. This isn’t just a song about sadness; it’s a full-bodied experience of mourning lost love. “Crying” resonated with listeners around the world, becoming one of Orbison’s signature tracks and securing his place in music history. It has since been covered by countless artists, yet few have matched the raw intensity of the original. Even today, it remains a masterclass in vocal delivery and emotional storytelling, proving that sometimes the simplest word—“crying”—can carry the weight of the world.
4. “In Dreams” (1963)
“In Dreams,” released in 1963, is a deeply evocative ballad that feels like stepping into a quiet, surreal dreamscape. The song’s unconventional structure defies pop norms, with no repeating chorus and a progression that mirrors the ebb and flow of a dream itself. Orbison’s voice floats gently at first, painting a picture of longing and love found in sleep, before rising to heart-wrenching heights as he realizes that the love he feels is only found in dreams. The song speaks to anyone who has ever clung to hope in the quiet moments of night, only to wake to reality. With each verse, the emotions swell—tenderness, hope, despair—until it crescendos in that unforgettable line: “But just before the dawn, I awake and find you gone.” The orchestral backing enhances the feeling of being suspended between sleep and reality. “In Dreams” was immortalized years later in David Lynch’s film Blue Velvet, introducing it to a new generation of listeners and adding to its mystique. It’s one of Orbison’s most haunting and imaginative songs, and a perfect example of how his music could transform something as personal as a dream into a universal emotional experience.
5. “Dream Baby (How Long Must I Dream)” (1962)
“Dream Baby (How Long Must I Dream)” presents a livelier, more upbeat side of Roy Orbison while still touching on his favorite theme—yearning for love. Released in 1962, the song is a bright blend of rockabilly and pop, featuring a rhythmic bounce that contrasts with the emotional content of the lyrics. Orbison sings with charm and urgency, voicing the impatience of someone who dreams constantly about the one they love but can’t seem to reach. His vocal phrasing is playful yet sincere, adding depth to a song that could easily come off as lighthearted. The instrumentation is snappy and engaging, with a driving beat that makes it nearly impossible not to tap your foot. Unlike some of his more brooding ballads, “Dream Baby” offers a taste of Orbison’s versatility—showing that he could deliver joy and longing in the same breath. It was a commercial hit that expanded his audience and highlighted his ability to cross genres. Though often overshadowed by his more dramatic numbers, “Dream Baby” remains a fan favorite and a prime example of Orbison’s capacity to make even longing feel fun.
6. “Running Scared” (1961)
Released in 1961, “Running Scared” is one of Roy Orbison’s most suspenseful and emotionally charged songs. What sets it apart is its unique structure—there’s no chorus, just a steady, dramatic buildup that mirrors the anxiety of the narrator. Orbison sings of a man terrified of losing the woman he loves to a former flame, and every verse ratchets up the tension. The orchestration starts soft and gentle, but grows in intensity alongside Orbison’s voice, culminating in a breathtaking finale. That final note—a soaring, powerful cry of triumph—is one of the most iconic moments in Orbison’s career. It delivers the emotional payoff the entire song builds toward, as the narrator discovers he has not been abandoned after all. The genius of “Running Scared” lies in how it mimics real emotional escalation, making the listener feel every ounce of dread, doubt, and, finally, relief. It’s a masterclass in musical storytelling, proof that Orbison could convey as much drama and tension in a two-minute song as most artists do in an entire album. Even decades later, the song’s structure, power, and emotional resonance remain unmatched.
7. “Blue Bayou” (1963)
“Blue Bayou,” released in 1963, is one of Roy Orbison’s most poignant and heartfelt tracks. The song paints a vivid picture of a man longing to return to a simpler life—back to the serene waters and familiar comforts of his home. Orbison’s voice is the emotional centerpiece, filled with longing and quiet desperation. He doesn’t just sing about missing home—he makes you feel the ache in your bones. The lyrics evoke imagery of moonlight on the bayou, fishing boats, and peaceful days, contrasting the narrator’s present life of sorrow and displacement. The instrumentation is lush yet understated, allowing Orbison’s vocals to shine while setting a dreamy, almost cinematic backdrop. “Blue Bayou” taps into universal emotions: homesickness, nostalgia, and the hope for a better tomorrow. Although it didn’t chart as high as some of his other hits initially, the song gained massive popularity over time—especially after Linda Ronstadt’s successful cover in the 1970s. Still, it’s Orbison’s original that carries that raw, aching honesty. “Blue Bayou” remains a beloved ballad that continues to resonate with listeners yearning for peace and belonging.
8. “You Got It” (1989)
“You Got It” is a stunning reminder that Roy Orbison’s brilliance didn’t fade with time. Released posthumously in 1989, the song became a triumphant return to form, proving his voice and songwriting could still hold their own in a new musical era. Co-written with Jeff Lynne and Tom Petty, it fuses classic Orbison melodicism with sleek late-’80s production. The result is a track that feels both nostalgic and refreshingly modern. Orbison’s voice—rich, soaring, and effortlessly expressive—is the star of the show. He sings about unconditional love with warmth and sincerity, making the listener feel every heartfelt promise. The chorus, with its soaring line “Anything you want, you got it,” is irresistibly catchy and emotionally resonant. “You Got It” introduced Orbison to a new generation, many of whom discovered his music through this song alone. It charted globally and remains a favorite in his catalog. What makes the track special is how it captures the timeless qualities of Orbison’s music: deep emotion, strong melody, and unforgettable vocals—all wrapped in a message of devotion and joy.
9. “It’s Over” (1964)
“It’s Over,” released in 1964, is a gut-wrenching ballad that showcases Roy Orbison at his most dramatic and emotionally intense. From the opening lines, the listener is plunged into a story of sudden heartbreak. Orbison’s voice is a force of nature here—tender and trembling one moment, then powerful and defiant the next. The orchestration swells and falls like a storm rolling in, building tension and emphasizing the finality of lost love. The refrain of “It’s over” is delivered with such piercing clarity that it feels like a dagger to the heart. What makes the song unforgettable is how Orbison holds nothing back—his performance captures the desperation, disbelief, and deep sadness that comes when a relationship ends without warning. It climbed the charts and became one of his signature songs, further solidifying his place as one of music’s most emotive performers. “It’s Over” remains a dramatic, operatic masterwork in the world of pop ballads, and a testament to Orbison’s unmatched ability to bring complex feelings to life with just his voice and a melody.
10. “Pretty Paper” (1963)
“Pretty Paper,” released in 1963, stands out among Roy Orbison’s songs as a tender holiday ballad filled with quiet sorrow and compassion. Written by Willie Nelson, the lyrics tell the story of a man selling wrapping paper on the streets during Christmas time—a figure easily overlooked by the bustling holiday crowd. Orbison’s gentle vocals bring depth and dignity to the character, asking listeners to pause and consider the humanity behind the festive rush. The melody is soft and slow, almost lullaby-like, allowing Orbison’s emotion to carry the narrative. His performance transforms a simple story into a powerful reflection on loneliness, generosity, and the true spirit of the season. Unlike many cheerful Christmas tunes, “Pretty Paper” urges empathy, reminding us that the holidays aren’t joyful for everyone. It’s this emotional honesty that has made the song endure through the decades. Orbison’s voice, full of grace and melancholy, makes “Pretty Paper” not just a Christmas classic but a moving tribute to the quiet dignity of those we often ignore.
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.
