Roy Orbison, often dubbed the “Big O,” is a legendary figure in the world of music, celebrated for his haunting voice and emotional depth. With a career spanning over three decades, Orbison crafted songs that resonate with listeners across generations. His unique blend of rock, pop, and country, coupled with his signature sunglasses and enigmatic persona, set him apart as one of the most influential artists of the 20th century.
In this article, we delve into the top 10 most popular Roy Orbison songs of all time, each a testament to his extraordinary talent. From soaring ballads that tug at the heartstrings to upbeat rock anthems that make you want to dance, Orbison’s catalog is rich with unforgettable melodies and poignant lyrics. Whether you’re a lifelong fan or new to his music, these iconic tracks capture the essence of Orbison’s artistry and the emotions he so masterfully conveyed. Join us as we explore the songs that not only defined his career but also left an indelible mark on the music landscape, ensuring that Roy Orbison’s legacy continues to shine brightly.
1. “Oh, Pretty Woman” (1964)
Released in 1964, “Oh, Pretty Woman” became an instant sensation and remains Roy Orbison’s signature hit. With its unforgettable guitar riff and strutting rhythm, the song captures the thrill of spotting someone captivating and wondering if there’s a chance at connection. Orbison’s voice moves with confidence and longing, blending charm with vulnerability in a way that few others could. The lyrics are simple but effective—he marvels at a beautiful woman walking by, daring to hope she might turn around. The song’s upbeat tempo, combined with Orbison’s operatic voice, gave it a unique blend of rock and pop that was both fresh and accessible. What really sets the track apart is how it balances playfulness with genuine emotion. It’s flirty without being shallow, catchy without being forgettable. “Oh, Pretty Woman” also found new life through countless covers and pop culture appearances, most notably in the 1990 film Pretty Woman, introducing it to new generations. The song’s iconic opening riff alone is enough to stir recognition, and once that voice kicks in, you’re hooked. It’s a perfect mix of swagger, sincerity, and timeless style, making it one of the most beloved songs in rock and roll history.
2. “Only the Lonely” (1960)
“Only the Lonely” marked a turning point for Roy Orbison in 1960, establishing him as more than just another rockabilly singer. This haunting ballad put his distinctive voice front and center, drawing listeners into a world of solitude and heartbreak. The lyrics speak directly to anyone who has felt the sting of being left behind, capturing the ache of loneliness with poetic simplicity. Orbison’s performance is heartbreakingly sincere—his quivering falsetto and dramatic crescendos turn sorrow into something strangely beautiful. The song’s production also stands out, with lush background vocals and a cinematic arrangement that builds tension and emotion throughout. At the time, it broke away from the standard sound of rock and roll, showing that the genre could also express vulnerability and emotional depth. “Only the Lonely” wasn’t just a hit—it was a revelation. It helped redefine male expression in popular music, proving that strength could exist alongside sadness. The song went on to influence countless artists and has remained a favorite for generations who find comfort in its melancholic melody. More than six decades later, its emotional weight still resonates, making it one of Orbison’s most important and enduring works.
3. “Crying” (1961)
Released in 1961, “Crying” is one of Roy Orbison’s most emotionally raw and vocally powerful songs. From the opening note, the track plunges listeners into the heartache of someone still reeling from lost love. The lyrics are unflinchingly honest—Orbison admits he’s not over a breakup, revealing that beneath the surface, he’s still devastated. What sets “Crying” apart is the way Orbison layers emotion throughout the performance, starting with a soft, almost whispered tone before building to a soaring climax. His vocal control is masterful, effortlessly shifting between registers to match the growing intensity of the song. The lush orchestration, including sweeping strings and dramatic crescendos, adds to the operatic feel, turning the song into something almost theatrical in its scope. At the time of its release, it defied the conventions of pop songwriting, offering a complex and deeply felt portrayal of heartbreak. Over the years, it has been covered by many artists—including a well-known duet with k.d. lang—but it’s Orbison’s original version that remains definitive. “Crying” isn’t just a song about sadness—it’s a cathartic experience, a moment of vulnerability that turns personal pain into timeless beauty. It stands as a cornerstone of Orbison’s legacy.
4. “Blue Bayou” (1963)
“Blue Bayou,” released in 1963, stands as one of Roy Orbison’s most poignant and evocative ballads. The song paints a vivid picture of a man yearning to return to a place of peace and familiarity—a bayou where life is simple, the sun shines bright, and his true love awaits. Orbison’s voice, filled with warmth and sorrow, carries the longing embedded in every lyric. There’s a soft lilt in his delivery that evokes the gentle sway of water, perfectly aligning with the imagery of the song. The blend of country and pop influences adds to the dreamlike atmosphere, supported by a slow, melodic rhythm and a delicate arrangement of strings and background vocals. “Blue Bayou” resonates because it’s not just about a location—it’s about the emotional pull of home, of comfort, and the ache of being separated from something cherished. While Linda Ronstadt’s cover later introduced the song to a new audience, Orbison’s original version remains unmatched in its sincerity and melancholy beauty. It’s a song that wraps you in emotion and carries you away, and it remains a shining example of Orbison’s ability to make deep emotion feel intimate and universal at the same time.
5. “Running Scared” (1961)
“Running Scared,” released in 1961, is a gripping musical journey that showcases Roy Orbison’s talent for building suspense and emotion through song. The lyrics unfold like a short story—one man walks in fear, worried that the woman he loves might leave him for someone from her past. Unlike many traditional pop songs of the time, “Running Scared” has no chorus. Instead, it climbs steadily, verse by verse, growing in tension until it explodes in a stunning finale. Orbison’s voice starts quietly, almost nervously, but with each line, he adds more force and desperation, culminating in a final, breathtaking high note that seals the emotional climax. The minimalist instrumentation early on allows Orbison’s voice to shine, while the dramatic orchestral swell toward the end mirrors the rising anxiety of the narrator. It’s storytelling through sound at its finest. “Running Scared” broke the mold of conventional song structure and proved that pop music could be cinematic and emotionally complex. Orbison’s performance is riveting—filled with anxiety, passion, and ultimately, relief. The payoff in the final line is unforgettable. Few songs manage to capture fear and love so vividly, and fewer still deliver such a satisfying emotional arc in under three minutes.
6. “In Dreams” (1963)
“In Dreams,” released in 1963, is one of Roy Orbison’s most haunting and imaginative pieces. The song unfolds like a surreal dream sequence, with each verse revealing more of the narrator’s heartache and longing. Orbison takes us through the delicate landscape of dreams, where love is briefly rekindled only to be lost again upon waking. What makes this track remarkable is its unique structure—it moves freely from one section to another without repeating choruses or verses, mimicking the fluid and unpredictable nature of dreams. Orbison’s voice is the centerpiece, effortlessly shifting from soft, almost whispered phrases to soaring high notes full of emotion. The orchestration is lush and cinematic, featuring gentle guitar lines, sweeping strings, and dramatic pauses that add to the song’s otherworldly mood. “In Dreams” captures a deeply human experience: the bittersweet comfort of dreams that offer what reality cannot. It became even more iconic after being featured in David Lynch’s Blue Velvet, where its eerie beauty took on an entirely new layer of meaning. But even without the cinematic connection, “In Dreams” stands on its own as a masterpiece of emotional storytelling. It’s a song that lingers long after it ends—like a powerful dream you can’t quite shake.
7. “Dream Baby (How Long Must I Dream)” (1962)
“Dream Baby (How Long Must I Dream),” released in 1962, is one of Roy Orbison’s more upbeat and lively tunes, showcasing a different side of his musical personality. Unlike his darker, more emotionally heavy ballads, this song is bright, rhythmic, and full of energy, with a rockabilly flair that instantly hooks the listener. The lyrics are simple but heartfelt—Orbison sings of dreaming about a love that’s just out of reach, a relatable longing that many have felt. His delivery is confident and smooth, giving the song an easy charm that contrasts with the heartache underneath the surface. The instrumentation features a steady, toe-tapping beat, catchy guitar riffs, and playful backing vocals that add to the fun, danceable quality. What really stands out is how Orbison takes a song with yearning at its core and transforms it into something joyful and catchy. “Dream Baby” proved that Orbison wasn’t just a master of slow, emotional ballads—he could also create infectious pop hits that felt light but still carried emotional weight. It’s a song that captures the innocence of young love and the universal feeling of dreaming about someone special, all wrapped in a cheerful, radio-ready package.
8. “You Got It” (1989)
“You Got It,” released in 1989, was a major comeback for Roy Orbison and a touching reminder of his enduring talent just before his untimely passing. Co-written with Jeff Lynne and Tom Petty, the song blends classic Orbison vocal style with modern ’80s production, creating a timeless anthem about unconditional love. Its lyrics are a simple but powerful pledge—whatever you want, whatever you need, I’ll give it to you. There’s a purity and sincerity in Orbison’s delivery that makes every line feel deeply personal. The upbeat tempo, crisp guitars, and lush harmonies give the track a fresh, optimistic energy while still staying true to Orbison’s emotional depth. It’s both nostalgic and forward-looking, reflecting the artist’s past while pointing to the possibilities of a new chapter. Tragically, Orbison died shortly after recording it, making “You Got It” one of his final gifts to the world. It became a global hit and reminded fans why his voice was so beloved—effortlessly powerful, tender, and timeless. The song remains a favorite not just because of its melody, but because it feels like a heartfelt message from Orbison himself—genuine, warm, and unforgettable.
9. “It’s Over” (1964)
“It’s Over,” released in 1964, is a sweeping ballad that captures the finality and heartbreak of a relationship’s end with haunting precision. Roy Orbison brings his signature operatic style to the forefront here, delivering each line with a dramatic intensity that builds to a crushing emotional peak. The song begins quietly, almost in disbelief, and grows into a soaring lament as the realization sets in—everything is truly over. The orchestration is grand and theatrical, with lush strings and rising crescendos that mirror the emotional collapse described in the lyrics. Orbison’s voice trembles with sorrow and strength all at once, making you feel every ounce of pain and resignation in the song’s narrative. What sets “It’s Over” apart is the way it dramatizes heartbreak not just as a feeling, but as an event—something that echoes through every part of a person’s life. It’s almost cinematic in its scope, and yet so personal in its impact. The song’s closing lines, shouted with devastating clarity, leave no room for ambiguity. For many listeners, “It’s Over” is one of Orbison’s most powerful and unforgettable performances, cementing his status as a true master of emotional storytelling through music.
10. “Pretty Paper” (1963)
“Pretty Paper,” released in 1963, is Roy Orbison’s tender take on a Christmas song, written by the legendary Willie Nelson. Unlike traditional holiday tunes that focus on joy and celebration, “Pretty Paper” turns our attention to the overlooked and forgotten—the man on the sidewalk, selling wrapping paper while everyone rushes by. Orbison’s gentle, heartfelt delivery turns this short song into something deeply meaningful. His voice is soft and reflective, filled with compassion and melancholy. The melody is simple and sweet, but the emotional undercurrent is powerful—it’s a reminder to slow down and notice those around us, especially during the holidays. The lyrics paint a vivid picture of loneliness during a time that’s supposed to be joyful, making it one of the most quietly profound Christmas songs ever recorded. Orbison’s version carries a warmth and sincerity that elevates the message, reminding us that the holiday season isn’t just about presents, but about kindness and awareness. “Pretty Paper” may not be as flashy as other seasonal hits, but its understated beauty and empathy have helped it endure as a classic. It’s a song that invites listeners to see with new eyes—and listen with an open heart.
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.
