Roy Orbison, the legendary voice of the 60s, continues to captivate audiences with his haunting melodies and emotionally charged lyrics. Often hailed as a pioneer of rock and roll, Orbison’s unique blend of pop, rock, and country has earned him a timeless place in music history. With his distinctive, soaring tenor and a flair for dramatic storytelling, he crafted songs that resonate with deep emotions—love, loss, and longing.
In a career that spanned decades, Orbison gifted the world with an array of classics that not only topped charts but also influenced generations of musicians. From the heart-wrenching balladry of “Crying” to the upbeat energy of “Pretty Woman,” his songs are etched in the fabric of American music culture.
As we explore the top 10 most popular Roy Orbison songs of all time, prepare to journey through his remarkable discography. Each track tells a story, echoing the trials and triumphs of the human experience. Whether you’re a lifelong fan or a newcomer to his music, these iconic hits promise to enchant and inspire, reminding us why Roy Orbison remains a beloved legend in the world of music.
1. Oh, Pretty Woman
Released in 1964, “Oh, Pretty Woman” is undeniably one of Roy Orbison’s most iconic and instantly recognizable hits. That unforgettable opening guitar riff grabs your attention from the first note and never lets go. What begins as a simple stroll down the street quickly becomes a magnetic tale of admiration, charm, and longing. Orbison’s smooth, confident vocals elevate what could have been a simple pop song into something enduringly special. With his trademark vibrato and emotional intensity, he brings genuine sincerity to the song’s flirty premise. The track became an instant classic, dominating the charts and eventually taking on a life of its own in pop culture—thanks in part to its inclusion in the hit film *Pretty Woman*. But beyond its commercial success, “Oh, Pretty Woman” captures the charm and romanticism that defined Orbison’s songwriting. It’s playful yet earnest, catchy yet meaningful. The fusion of rock, pop, and a touch of doo-wop gives the track a timeless quality that continues to resonate decades later. It’s not just a song—it’s a moment in time, preserved by Orbison’s masterful performance and the universal nature of its message: the awe of unexpected beauty.
2. Only the Lonely
“Only the Lonely,” released in 1960, marked a turning point in Roy Orbison’s career, solidifying his reputation as one of music’s most emotionally resonant voices. From the opening lines, the song envelops listeners in a world of quiet heartbreak and isolation. Orbison’s voice, soaring effortlessly between vulnerable lows and operatic highs, communicates more than just lyrics—it captures the very essence of loneliness. The orchestral backdrop adds a cinematic quality, with gentle strings and backing vocals that enhance the melancholy tone without overwhelming it. What makes this song so powerful is its emotional authenticity. Orbison doesn’t just sing about pain—he lives it in every note, making the listener feel like they’ve been handed a key to his innermost sorrow. The song became an international hit and helped establish the blueprint for the emotionally rich ballads that would become Orbison’s signature. “Only the Lonely” remains a defining track in the canon of classic rock and pop, not just for its musical beauty, but for the way it articulates an experience so many know but struggle to express. It’s heartbreak turned into high art.
3. Crying
Released in 1961, “Crying” is a masterclass in vocal control, emotional depth, and lyrical vulnerability. Roy Orbison doesn’t just sing this song—he pours his soul into every word, turning heartbreak into a form of art. The track opens quietly, almost gently, lulling the listener into a calm before building toward a powerful emotional crescendo. As the song progresses, the arrangement swells with strings and backing harmonies, mirroring the growing intensity of the sorrow he’s expressing. The lyrics depict the moment when one realizes they’re still not over a love lost—when tears come long after you thought they were gone. Orbison’s voice trembles with genuine emotion, especially during the climactic final lines where he belts the word “crying” with such force that it becomes unforgettable. It’s no surprise that this track has been covered by dozens of artists over the decades—from Don McLean to k.d. lang—because its message is both universal and timeless. But no version quite captures the raw beauty and aching honesty of Orbison’s original. “Crying” isn’t just a sad song—it’s a landmark in pop balladry and a testament to Orbison’s rare gift for emotional storytelling.
4. Pretty Paper
“Pretty Paper,” released in 1963, is Roy Orbison’s unique and heartfelt entry into the holiday music canon. Written by Willie Nelson and brought to life through Orbison’s tender voice, the song offers more than just seasonal cheer—it paints a poignant portrait of unseen hardship amidst festive joy. The story centers on a street vendor selling wrapping paper and ribbons, someone often overlooked in the holiday rush. Orbison’s delivery is full of empathy, turning a simple narrative into a moving reminder about compassion, loneliness, and the quieter struggles that can accompany the holiday season. The melody is soft and warm, allowing the bittersweet lyrics to shine through. Unlike many Christmas songs that focus on bright lights and merry tunes, “Pretty Paper” is introspective and grounded in real human emotion. Orbison’s ability to channel sincere emotion gives the song its lasting impact. It invites listeners to slow down, to look beyond the glitter, and to consider the people we might otherwise miss. “Pretty Paper” continues to resonate with those who appreciate songs that combine storytelling, melody, and a deeper message of kindness during a time that’s often both joyful and heavy.
5. In Dreams
“In Dreams,” released in 1963, is perhaps one of the most imaginative and emotionally resonant songs in Roy Orbison’s catalog. From its spoken introduction to its haunting conclusion, the track unfolds like a lucid dream—fluid, surreal, and deeply affecting. Orbison sings of a love so powerful it transcends reality, existing only in the refuge of sleep. The structure of the song is unconventional, lacking a traditional chorus or repeated hook. Instead, it flows like a narrative, building momentum as Orbison’s vocal range expands with each verse. His performance moves from gentle crooning to a soaring climax, capturing the listener in a whirlwind of emotion. The orchestration is equally evocative, with lush strings and piano that accentuate the dreamlike atmosphere. “In Dreams” is both beautiful and heartbreaking, exploring the pain of losing someone while cherishing the moments they live on in memory. The song gained renewed popularity after being featured in David Lynch’s *Blue Velvet*, introducing Orbison’s haunting performance to a new generation. It remains a stunning example of his artistry—a song where emotion, melody, and storytelling merge seamlessly to create something timeless and transcendent.
6. Running Scared
Released in 1961, “Running Scared” is one of Roy Orbison’s most dramatic and cinematic songs. What begins with a quiet, almost uncertain introduction slowly builds into an emotional crescendo that leaves listeners breathless by the final note. The song tells the story of a man who fears he’s about to lose the woman he loves to a former flame, a narrative that unfolds with mounting tension. The arrangement is minimal at first, giving Orbison’s voice space to deliver each word with aching vulnerability. As the story reaches its climax, the music swells, and Orbison’s vocals soar in one of the most powerful endings in pop music history—without a chorus, no less. It’s a masterstroke in storytelling and dynamics, a song that keeps listeners on edge until its very last second. What sets “Running Scared” apart is Orbison’s ability to convey raw emotion so honestly. You don’t just hear the fear and hope in his voice—you feel it. The unexpected twist ending, where the girl chooses to stay, provides a rare sense of triumph, making the journey all the more satisfying. It’s a perfect blend of suspense, romance, and heartbreak, wrapped in just under three minutes of musical brilliance.
7. It’s Over
“It’s Over,” released in 1964, is Roy Orbison at his most emotionally intense. The title alone sets the tone for a song steeped in finality and heartbreak. With lyrics that evoke the aftermath of a love that has come to an undeniable end, Orbison delivers each line with a heart-wrenching sincerity that makes it feel personal—even if you’ve never experienced that kind of loss. The orchestration is lush and grand, yet it never overshadows Orbison’s voice, which remains the centerpiece. He moves effortlessly from a soft whisper to a powerful crescendo, embodying the anguish of letting go. There’s something almost theatrical in the way the song unfolds, yet it never crosses into melodrama—it’s too real, too raw. Every element, from the sweeping strings to the quiet pauses, works together to create a sense of emotional gravity. “It’s Over” isn’t just about romantic heartbreak—it’s about the emotional wreckage that follows, the silence after love fades. It remains one of Orbison’s most compelling performances, a track that perfectly captures the universal pain of saying goodbye when there’s nothing left to fight for. It’s haunting, elegant, and utterly unforgettable.
8. Blue Bayou
“Blue Bayou,” released in 1963, is a gentle, wistful ballad that transports listeners to a place of peace, love, and longing. With a melody as calm and flowing as the waters it describes, the song tells the story of a man dreaming of returning to a simpler, happier time and place—somewhere he felt whole. Orbison’s voice is perfectly suited for this kind of nostalgic storytelling. His delivery is tender yet full of yearning, making the listener feel every ounce of the ache to return to what’s been lost. The song’s title became synonymous with a sense of escapism, a longing not just for a physical place but for the emotional sanctuary that place represents. Backed by gentle guitar strums and a lulling rhythm, “Blue Bayou” has an almost lullaby-like quality. It’s soothing and emotional at once, allowing listeners to drift away with each verse. Though covered famously by Linda Ronstadt years later, Orbison’s original remains deeply beloved for its vulnerability and quiet beauty. “Blue Bayou” reminds us that sometimes the greatest comfort comes not in change, but in the dream of going home.
9. You Got It
“You Got It,” released in 1989, was Roy Orbison’s remarkable return to the spotlight after years away from the mainstream. Tragically, it was released posthumously, but the song stands as a joyful and triumphant reminder of his enduring talent. With its upbeat tempo and radiant optimism, “You Got It” feels like a love letter not only to a special person but also to life itself. The lyrics express total devotion—”Anything you want, you got it”—delivered with warmth and sincerity. Orbison’s voice, undiminished by time, is just as rich and powerful as ever. The production, overseen by Jeff Lynne and Tom Petty, gives the song a crisp, modern feel while still honoring Orbison’s classic sound. It became a worldwide hit, introducing his music to a new generation and reminding older fans of the timeless quality of his voice. There’s a joy in this song that feels infectious—hopeful, uplifting, and filled with genuine love. “You Got It” serves as a beautiful coda to Orbison’s career, a song that encapsulates everything that made him special: a golden voice, a big heart, and a talent that truly never faded.
10. Dream Baby (How Long Must I Dream)
“Dream Baby (How Long Must I Dream),” released in 1962, is one of Roy Orbison’s more energetic and upbeat tracks, blending rockabilly flair with pop charm. Unlike his more somber ballads, this song is playful, even a bit flirtatious, as it tells the story of someone who’s hopelessly infatuated and dreaming about being with the one they love. The lively rhythm and catchy melody make it an instant toe-tapper, while Orbison’s clear, expressive vocals keep it rooted in genuine emotion. There’s an urgency in the lyrics, a yearning that adds depth to what could otherwise be just a feel-good pop tune. The guitar work and backing vocals give the track a rhythmic bounce, making it stand out in Orbison’s discography for its breezy, radio-ready appeal. Even with its lighter tone, “Dream Baby” maintains the heartfelt core that defines Orbison’s best work. It’s the sound of early ’60s pop at its most infectious, a song that captures both the innocence and intensity of young love. Whether you’re dancing along or daydreaming yourself, “Dream Baby” is a delightful gem that continues to charm listeners with its warmth and energy.
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.
