Roy Orbison, a musical legend whose voice could melt hearts and stir souls, left an indelible mark on the landscape of rock and roll. With his signature sunglasses and hauntingly beautiful ballads, Orbison became a beacon of emotion in a genre often dominated by bravado. His songs, characterized by deep lyrical content and soaring melodies, not only topped the charts but also resonated with generations of listeners. From the passionate yearning of “Crying” to the anthemic power of “Pretty Woman,” Orbison’s repertoire showcases his unique ability to convey love, loss, and longing.
As we delve into the top 10 most popular Roy Orbison songs of all time, prepare to journey through his musical genius. Each track tells a story, transporting us to a world where heartbreak and hope collide. These songs are more than just tunes; they are timeless classics that continue to inspire artists and fans alike. Whether you’re a lifelong fan or new to his work, this list will shine a spotlight on the incredible artistry of Roy Orbison—an artist whose influence remains as powerful today as it was during his heyday. Get ready to rediscover the magic of Roy Orbison!
1. Oh, Pretty Woman (1964)
Released in 1964, “Oh, Pretty Woman” is one of Roy Orbison’s most iconic and enduring hits. The song immediately captures attention with its upbeat tempo, unforgettable melody, and irresistible hook, making it a staple of pop culture. With his signature, soaring voice, Orbison sings about a chance encounter with a beautiful woman on the street, infusing the song with an infectious sense of urgency and longing. The lyrics—simple yet powerful—express a sense of instant infatuation and a desperate desire to win the heart of the woman he sees. What truly sets “Oh, Pretty Woman” apart is Orbison’s vocal delivery, which is both tender and passionate, perfectly complementing the upbeat instrumental arrangement. The song’s driving rhythm and lively instrumentation bring a sense of excitement, while Orbison’s voice adds a touch of vulnerability, as he paints a picture of a man lost in love at first sight. “Oh, Pretty Woman” was not only a commercial success, but it also became a cultural phenomenon. It topped the charts and solidified Orbison’s place as one of rock and roll’s most powerful vocalists. Its influence extends beyond music, with the song being featured in countless films, TV shows, and commercials over the years, ensuring that it remains firmly planted in popular culture. Orbison’s ability to blend romance, longing, and charm in a catchy, upbeat package is what makes “Oh, Pretty Woman” timeless, an anthem of infatuation that still resonates with listeners today. The song is a testament to Orbison’s songwriting talent and vocal prowess, capturing the magic of love at first sight and making it a timeless classic.
2. Only the Lonely (1959)
Released in 1959, “Only the Lonely” showcases Roy Orbison’s ability to blend deep heartache with soaring, haunting melodies, creating a ballad that has become a defining moment in his career. The song is a heartfelt expression of isolation and despair, as Orbison sings about a person left alone and longing for a lost love. The opening notes immediately set the tone, with the orchestra building a dramatic, melancholic backdrop that perfectly complements Orbison’s plaintive, almost haunting vocals. He sings with such raw emotion, pulling listeners into a world of loneliness and yearning, making “Only the Lonely” one of the most emotionally compelling songs in the rock and roll genre. The lyrics themselves are both simple and profound, capturing the universal experience of being heartbroken and feeling abandoned. Orbison’s voice soars to emotional heights, and his vocal range is showcased brilliantly in every verse, especially during the iconic “lonely” refrain that leaves a lasting impact on the listener. While “Only the Lonely” is an exploration of sadness and heartache, it is also an anthem of resilience, as it recognizes that loneliness is a part of life that must be endured. The lush orchestral arrangement elevates the song, adding to its dramatic intensity and giving it a timeless quality. The song’s success not only helped launch Orbison’s career but also established him as a master of the emotional ballad. “Only the Lonely” remains one of his most beloved songs, resonating with generations of listeners who find comfort in its portrayal of heartache and the shared experience of loneliness.
3. Crying (1961)
Released in 1961, “Crying” stands as one of Roy Orbison’s most emotionally powerful songs, offering a haunting exploration of heartbreak, vulnerability, and the devastation of lost love. The song opens with a mournful, orchestral introduction that immediately sets a sorrowful tone. As Orbison begins to sing, his voice trembles with the weight of emotion, drawing listeners into a deep well of sadness. His vocal delivery is nothing short of mesmerizing—rich and resonant, with each note dripping with the pain of unrequited love. “Crying” tells the story of a man who witnesses his lover moving on, and he is left to grapple with the painful reality of loss. The lyrics are beautifully simple yet devastatingly poignant, capturing the universality of heartbreak. As Orbison reaches the climax of the song, his voice soars, delivering the raw emotional intensity of the words, particularly during the repeated refrain, “I’m crying over you.” The song’s arrangement features lush strings, delicate piano, and a heartbeat-like rhythm that mirrors the steady pulse of sadness throughout the track. This lush instrumentation perfectly complements Orbison’s delivery, making the song feel as grand as it is intimate. Over the years, “Crying” has become a hallmark of Orbison’s style—melancholic yet mesmerizing, heart-wrenching yet beautiful. Its timeless appeal has led to numerous covers by artists across various genres, solidifying “Crying” as one of Orbison’s most enduring and influential songs. Through its raw emotion and captivating arrangement, “Crying” continues to resonate with listeners, evoking the feelings of sorrow and longing that are universally experienced in the wake of a lost love.
4. In Dreams (1963)
Released in 1963, “In Dreams” is a captivating ballad that transports listeners into a surreal world where love and fantasy intertwine. With its haunting, dreamlike quality, the song represents a departure from the traditional love song, offering a glimpse into the subconscious mind of someone who longs for a love that is unattainable in reality. Orbison’s ethereal, multi-layered vocals carry the listener through a journey of dreams, where his love transcends the boundaries of the real world. The song’s lush orchestration, complete with sweeping strings and a soft, atmospheric rhythm, creates a feeling of surrealism that perfectly matches the lyrics. In “In Dreams,” Orbison paints a vivid picture of a romantic dream, in which his lost love reappears to him, only to vanish when he wakes. This sense of both joy and melancholy is conveyed masterfully through Orbison’s voice, which floats effortlessly between sweetness and sadness. His delivery is tender yet haunting, and his ability to evoke such a deep emotional response with each note is what makes this song so timeless. The lyrics themselves are imbued with longing and a sense of yearning, as Orbison expresses his desire for a love that exists only in his dreams. “In Dreams” stands as a testament to Orbison’s vocal versatility, as he moves between soft, intimate moments and dramatic crescendos, leaving an indelible emotional impact on the listener. This ballad has become one of Orbison’s most beloved tracks, showcasing his ability to blend the fantastical with the deeply emotional in a way that few artists have managed to replicate. Its dreamlike atmosphere continues to captivate audiences, making it a true classic in Orbison’s catalog.
5. Running Scared (1961)
Released in 1961, “Running Scared” is a dramatic and suspenseful narrative that showcases Roy Orbison’s ability to tell a story through his music while conveying deep emotional tension. The song tells the tale of a man desperate to hold on to the woman he loves, fearing that another suitor will steal her away. The track is built around a sense of urgency and desperation, with Orbison’s rich baritone voice adding to the dramatic tone of the lyrics. As the song progresses, the orchestration builds in intensity, mirroring the emotional stakes of the story, with strings soaring and rhythms quickening. The instrumental arrangement plays a key role in heightening the sense of tension, as it mimics the racing heartbeat of someone on the verge of losing everything. Orbison’s vocals are masterful, capturing the anxiety and longing of someone in love, yet unsure of their place in their lover’s heart. The raw emotion he conveys with every line adds a layer of depth to the song, making it more than just a story of jealousy and fear—it becomes a reflection of the vulnerability that comes with love. The urgency in his delivery makes it clear that this is a man who is willing to do whatever it takes to keep his love, even as he realizes the possibility of losing her. “Running Scared” is an exceptional example of Orbison’s ability to blend storytelling with emotional resonance, crafting a song that is both gripping and deeply relatable. Its vivid imagery and soaring vocals make it a standout in Orbison’s catalog, continuing to captivate listeners with its dramatic narrative and intense emotional pull.
6. Dream Baby (How Long Must I Dream) (1962)
In 1962, Roy Orbison released “Dream Baby (How Long Must I Dream),” a song that blends catchy melodies with deep emotional longing. The track speaks to the universal experience of yearning for love that feels just out of reach, offering a window into the singer’s emotional state as he pines for a romance that has yet to materialize. The upbeat rhythm and infectious melody create a paradox of emotions—while the music invites listeners to dance, the lyrics convey a sense of unfulfilled desire. Orbison’s voice is both powerful and tender as he sings about his dreams of the woman he loves, asking how long he must wait to make those dreams a reality. The song’s arrangement features bright, energetic instrumentation, including shimmering guitars and lush strings, which bring a sense of optimism to the otherwise wistful lyrics. This juxtaposition between the upbeat sound and the bittersweet theme of unrequited love creates a captivating contrast that defines much of Orbison’s work. His ability to convey a deep yearning with such infectious energy showcases his unique talent as a vocalist and songwriter. “Dream Baby” captures the bittersweet side of love—the excitement of wanting someone while acknowledging the frustration of longing. The song quickly became a hit, climbing the charts and reinforcing Orbison’s status as one of the era’s most influential vocalists. The track also marked a key moment in Orbison’s career, demonstrating his ability to blend catchy pop sensibilities with emotional depth. To this day, “Dream Baby” remains one of Orbison’s most endearing tracks, with its timeless melody and relatable lyrics continuing to resonate with listeners around the world.
7. It’s Over (1964)
Released in 1964, “It’s Over” is one of Roy Orbison’s most haunting ballads, capturing the raw emotion of a relationship’s painful end. From the moment the song begins, the listener is enveloped in a somber atmosphere created by the lush orchestral arrangement and the deep sorrow conveyed in Orbison’s voice. The song tells the story of a man coming to terms with the end of a love that once seemed everlasting. Orbison’s vocals are particularly powerful in this track, as he expresses the crushing finality of heartbreak with such intensity that it feels deeply personal. His ability to sing about love’s end with such vulnerability and emotional depth is what makes “It’s Over” one of his most poignant tracks. The orchestration, which includes sweeping strings and dramatic percussion, enhances the feeling of loss, creating a sense of grandeur that reflects the magnitude of the heartbreak being described. The lyrics, simple yet devastating, capture the final moments of a relationship that is slipping away, leaving the protagonist to face the inevitability of its demise. The song’s universal theme of love lost resonated deeply with listeners, making it an instant classic. “It’s Over” stands as a testament to Orbison’s skill as both a vocalist and a storyteller, capturing the deep sorrow of a love that cannot be salvaged. The track continues to move audiences, thanks to its emotional honesty and the unmistakable power of Orbison’s voice. To this day, “It’s Over” remains one of the definitive heartbreak anthems, with its dramatic delivery and timeless melody cementing its place in Orbison’s legendary catalog.
8. Blue Bayou (1963)
Released in 1963, “Blue Bayou” is a hauntingly beautiful song that evokes feelings of longing and nostalgia, demonstrating Roy Orbison’s ability to convey deep emotion through his voice and lyrics. The song transports listeners to a serene, yet melancholic place, where the protagonist yearns for the peacefulness and simplicity of his past. The lyrics speak of a love that has been lost, and the singer dreams of returning to a place where everything felt right. Orbison’s smooth, emotive vocals are perfectly suited to the mood of the song, delivering each word with a sense of aching longing. His voice conveys the deep sense of loss and desire to return to a better time, and the chorus, with its repeated “Blue Bayou,” evokes an image of a tranquil, idyllic place that now exists only in memory. The instrumentation of “Blue Bayou” complements Orbison’s vocals, with gentle acoustic guitars and lush strings creating an atmosphere that is both soothing and sorrowful. The song’s blend of melancholy and serenity is what makes it so compelling, as it speaks to a universal desire for reconciliation with the past. Orbison’s interpretation of the song captures a yearning for a love and a time that can never be recaptured, but the beauty of the track lies in the feeling that, even in loss, there is something deeply peaceful in the memory. “Blue Bayou” stands out as one of Orbison’s finest moments, showcasing his ability to capture the complexity of human emotions with a simple yet evocative arrangement. It remains one of his most beloved songs, cherished for its timeless beauty and emotional depth.
9. Pretty Paper (1963)
In 1963, Roy Orbison released “Pretty Paper,” a holiday classic that blends warmth with bittersweet nostalgia, creating a song that is as heartwarming as it is heartbreaking. The song tells the story of a lonely street vendor during Christmas, selling his wares while surrounded by the festive cheer that he himself cannot partake in. Orbison’s tender vocals bring a sense of melancholy to the track, capturing the vendor’s isolation as he watches others enjoy the holiday season. The imagery in the lyrics evokes a sense of empathy, and the simple act of the vendor selling “pretty paper” becomes a symbol of the giving spirit of Christmas, as well as the quiet loneliness that can accompany the season. The gentle melody, paired with the lush orchestration, enhances the song’s emotional impact, creating a feeling of warmth despite the underlying sadness. Orbison’s ability to evoke such a deep sense of empathy through his voice and lyrics is what makes “Pretty Paper” so memorable. It is a holiday song that stands apart from others, as it does not simply celebrate the joy of the season, but also acknowledges the sorrow that can accompany it. “Pretty Paper” has become a beloved holiday classic, its timeless message of kindness and compassion resonating with listeners every year. Orbison’s ability to capture the complexity of emotions during the holiday season, mixing feelings of joy with the reality of loneliness, makes this song a standout in his catalog. Its gentle melody and emotional depth continue to make it a favorite, ensuring its place as a Christmas classic.
10. You Got It (1989)
Roy Orbison’s 1989 hit “You Got It” marked a triumphant return for the rock and roll legend, showcasing his timeless voice and songwriting skills. The song features a smooth, catchy melody that blends effortlessly with Orbison’s rich vocals, creating a sound that is both contemporary and nostalgic. “You Got It” is a celebration of love, connection, and admiration, with Orbison singing about the undeniable magnetic pull of a lover. The lyrics are simple yet powerful, capturing the essence of a relationship that feels destined, and Orbison’s performance is filled with sincerity and warmth. His voice, as commanding as ever, effortlessly conveys the sense of devotion and longing present in the song, reminding listeners of his incredible vocal range and emotional depth. The upbeat rhythm and smooth instrumentation give the song an infectious energy, making it impossible not to tap along to the beat. “You Got It” became an instant hit, climbing the charts and reminding audiences of the enduring power of Orbison’s music. The song’s success marked a revitalization of his career and cemented his place as a music icon. Despite the time gap between his earlier hits and “You Got It,” Orbison’s voice had not lost any of its emotive power, proving that his artistry transcends generations. With its catchy chorus, heartfelt lyrics, and timeless delivery, “You Got It” stands as one of Orbison’s most beloved tracks, serving as a fitting tribute to his musical legacy and confirming that, even after decades, his voice and talent were as captivating as ever.
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.
