Roy Orbison, the enigmatic “Caruso of Rock,” possessed a voice that could soar to celestial heights and plunge into the deepest emotional depths, leaving listeners spellbound with every note. His music transcended genres, blending rock and roll, country, and pop into a sound that was uniquely his own. With his signature dark sunglasses and hauntingly beautiful melodies, Orbison carved out a legacy as one of the most beloved and influential artists in music history.
From heart-wrenching ballads to electrifying rock anthems, Orbison’s songs captured the full spectrum of human emotion—love, longing, triumph, and heartbreak. Decades after their release, his timeless hits continue to resonate with audiences around the globe, proving that great music is truly eternal. Whether you’re a lifelong fan or discovering his genius for the first time, diving into Roy Orbison’s greatest tracks is an unforgettable journey.
In this article, we celebrate the magic of Roy Orbison by counting down his top 10 most popular songs of all time. These iconic tracks showcase the unparalleled artistry and soul-stirring passion that made Orbison a legend. Get ready to rediscover the hits that defined an era and continue to captivate generations of music lovers!
1. Only the Lonely (Know the Way I Feel) – 1960
Roy Orbison’s “Only the Lonely (Know the Way I Feel)” was the song that truly established him as a force in rock and roll. Released in 1960, this melancholic ballad captured the universal feeling of heartbreak with a haunting vocal performance that set him apart from his contemporaries. At the time, rock and roll was dominated by energetic, danceable tracks, but Orbison’s approach was different—he brought operatic intensity to his delivery, soaring effortlessly into his signature falsetto.
The song’s orchestral arrangement was groundbreaking, featuring lush strings and a dramatic build-up that added to its emotional weight. Orbison originally wrote it with Elvis Presley or the Everly Brothers in mind, but when they passed on it, he recorded it himself. The decision turned out to be life-changing, as the song climbed to #2 on the Billboard Hot 100 and became his breakthrough hit.
With lyrics that speak to the crushing isolation of lost love, “Only the Lonely” struck a deep chord with listeners. It was more than just a song—it was an experience, one that made people feel seen in their sadness. The track also pioneered the sound that would become Orbison’s trademark: dramatic storytelling, orchestral arrangements, and emotionally charged vocals. Over six decades later, the song remains a timeless classic, proving that loneliness, heartbreak, and longing are emotions that transcend generations.
2. Crying – 1961
Few songs capture the agony of lost love as powerfully as “Crying.” Released in 1961, this heart-wrenching ballad takes listeners on an emotional journey from quiet sorrow to an overwhelming outpouring of grief. Orbison’s voice is the star here, beginning in a soft, reflective tone before soaring into an operatic climax filled with raw, tearful emotion.
The song was inspired by a real-life encounter with an ex-lover, which left Orbison feeling overwhelmed with sadness. That sense of personal pain is woven into every note, making “Crying” one of the most authentic and emotionally stirring songs in his catalog. The dramatic orchestral backing adds to the weight of the lyrics, slowly building until it reaches a cathartic crescendo where his voice practically weeps alongside the melody.
Upon its release, “Crying” was a massive hit, reaching #2 on the Billboard Hot 100 and cementing Orbison’s reputation as a master of emotional storytelling. Over the years, it has been covered by many artists, including Don McLean, whose version also gained significant popularity. The song was later inducted into the Grammy Hall of Fame, a testament to its enduring impact.
Orbison himself considered “Crying” one of his finest works, and listening to it today, it’s easy to see why. The song is a masterclass in vocal control, emotion, and the ability to make heartbreak sound utterly beautiful.
3. Oh, Pretty Woman – 1964
When you think of Roy Orbison, one of the first songs that comes to mind is “Oh, Pretty Woman.” Released in 1964, this upbeat, infectious track became one of the biggest hits of his career, topping the Billboard Hot 100 and reaching #1 in multiple countries. Decades later, it remains one of the most recognizable songs in rock and roll history.
From the very first note, “Oh, Pretty Woman” grabs your attention with its iconic guitar riff—one of the most memorable in rock music. The song tells the story of a man admiring a beautiful woman as she walks by, blending playful flirtation with a hint of longing. The lyrics, coupled with Orbison’s smooth yet powerful vocals, give the song a lighthearted charm that contrasts with his more melancholic ballads.
The song’s success was immediate, selling millions of copies worldwide. It became even more famous in the late ’80s after being prominently featured in the film Pretty Woman, starring Julia Roberts and Richard Gere. The film’s success reintroduced the song to a new generation, ensuring its legacy lived on.
While Orbison was known for his sorrowful ballads, “Oh, Pretty Woman” proved he could also create energetic, feel-good rock and roll. It’s a song that has stood the test of time, still played regularly on classic rock stations and used in pop culture. More than just a hit, it’s an anthem of admiration, romance, and classic rock brilliance.
4. In Dreams – 1963
Roy Orbison’s “In Dreams” is a hauntingly beautiful ballad that showcases his ability to create vivid, cinematic storytelling through music. Released in 1963, this song is unlike most pop songs of its time—it doesn’t follow a traditional verse-chorus structure but instead unfolds like a dream, with an evolving melody that builds in intensity. This unique arrangement, combined with Orbison’s ethereal vocals, gives the song an almost otherworldly quality.
The lyrics tell the story of a man who finds joy in his dreams, where he can be with the one he loves—only to wake up and face the painful reality that she’s gone. The emotional weight of this realization is mirrored in Orbison’s soaring vocal performance, which moves effortlessly from delicate whispers to powerful cries. The orchestral backing only adds to the song’s dreamlike, melancholic atmosphere.
Though “In Dreams” was a hit upon its release, it gained even greater recognition in 1986 when it was prominently featured in David Lynch’s film Blue Velvet. The film’s eerie and surreal nature perfectly matched the song’s dreamlike quality, introducing it to a new generation of listeners. Orbison was initially surprised by the film’s use of the song, but he later embraced its renewed popularity.
To this day, “In Dreams” remains one of Orbison’s most beloved and emotionally stirring songs. Its haunting beauty and deeply personal lyrics ensure that it continues to resonate with listeners, proving that Orbison was not just a singer—he was a storyteller who could transport his audience to another world.
5. Running Scared – 1961
“Running Scared” is one of Roy Orbison’s most unique and dramatic songs, released in 1961 as part of his ever-growing catalog of emotionally charged ballads. What sets this song apart is its structure—there is no chorus, only a continuous build-up of tension that culminates in an unforgettable, powerful climax.
The lyrics tell the story of a man who lives in fear that his love will leave him for someone else. As the song progresses, so does the intensity, mirroring the narrator’s growing anxiety. The instrumentation starts softly but gradually swells, adding to the song’s suspense. By the time Orbison reaches the final lines—delivered in a stunning, unbroken high note—the listener is left breathless, completely immersed in the emotional journey.
Upon its release, “Running Scared” topped the Billboard Hot 100, becoming Orbison’s first #1 hit. Its dramatic composition and haunting melody set it apart from other songs of the era, proving that Orbison wasn’t just a typical rock and roll star—he was an innovator.
The song’s influence can be heard in many artists who came after him, from operatic rock singers to modern balladeers. Even today, “Running Scared” remains a testament to Orbison’s ability to push the boundaries of pop music and create something truly unforgettable.
6. It’s Over – 1964
Few breakup songs hit as hard as “It’s Over.” Released in 1964, this heartbreaking ballad captures the finality of a relationship’s end with devastating clarity. Orbison’s voice, filled with sorrow and longing, guides the listener through the pain of realizing that love is truly gone.
Lyrically, the song is a masterclass in emotional storytelling. The imagery of fading sunsets and a love slipping away gives it a poetic quality, making it feel almost like a farewell letter set to music. The orchestral arrangement builds slowly, reinforcing the feelings of loss and inevitability. Unlike many songs that dwell on hope or the possibility of reconciliation, “It’s Over” offers no such comfort—it is pure, unfiltered heartbreak.
When the song was released, it quickly became a major hit, reaching #1 in the UK and solidifying Orbison’s place as one of the great ballad singers of his time. It also showcased his ability to convey deep emotion in just a few minutes, a skill that few artists possess.
Over the years, “It’s Over” has been covered by numerous artists, but none can match the sheer intensity of Orbison’s original recording. His voice, filled with pain and resignation, makes it clear—when love is over, there’s nothing left but the silence it leaves behind.
7. Blue Bayou – 1963
Roy Orbison’s “Blue Bayou” is a song that instantly transports listeners to another place. Released in 1963, this dreamy ballad paints a picture of a man longing to return to his peaceful, sunlit home by the bayou, far away from the struggles of city life. With its gentle melody and vivid storytelling, “Blue Bayou” remains one of Orbison’s most beloved songs.
Unlike some of his more dramatic heartbreak songs, “Blue Bayou” carries a sense of nostalgia and longing rather than sorrow. The song’s slow, rolling rhythm and Orbison’s soothing vocals create a sense of calm, as if he’s reminiscing about a place that exists only in his memories. The melody, inspired by country and folk influences, gives it a timeless quality that has allowed it to endure for decades.
The song took on a new life in the 1970s when Linda Ronstadt recorded a version that became one of her biggest hits. While her rendition brought it back into the mainstream, Orbison’s original remains unmatched in its emotional depth and sincerity.
Whether listened to on a quiet night or a long road trip, “Blue Bayou” has the power to make anyone long for a place they once called home—or a dream of a home they’ve yet to find.
8. Dream Baby (How Long Must I Dream) – 1962
Roy Orbison’s “Dream Baby (How Long Must I Dream)” is a lively, infectious tune that highlights his ability to blend rock and roll energy with heartfelt lyricism. Released in 1962, the song marked a shift from Orbison’s signature ballads toward a more upbeat, rhythmic sound. With its playful lyrics and catchy melody, it quickly became a fan favorite and a major hit.
Unlike Orbison’s more melancholic songs about lost love and heartache, “Dream Baby” carries a sense of optimism and longing. The lyrics express a yearning for love, with the singer daydreaming about the moment when his feelings will be reciprocated. The bright instrumentation, driven by a steady beat and twangy guitar, gives the song an irresistible groove, making it a standout in Orbison’s catalog.
The song became a top 10 hit in both the U.S. and the UK, proving that Orbison could master multiple styles beyond his signature dramatic ballads. It has since been covered by several artists, including Glen Campbell, but Orbison’s version remains the definitive one.
With its upbeat charm and timeless melody, “Dream Baby” continues to bring joy to listeners, reminding them of the thrill of waiting for love to finally become real.
9. You Got It – 1989
“You Got It” stands as one of the most bittersweet songs in Roy Orbison’s catalog. Released in 1989, just months after his tragic passing, the song became a posthumous hit, introducing his unmistakable voice to a new generation. Co-written with Jeff Lynne and Tom Petty, “You Got It” blends Orbison’s classic style with modern production, creating a song that feels both timeless and fresh.
Lyrically, the song is a heartfelt declaration of love and devotion. Orbison sings about giving everything to the person he loves, promising unwavering commitment. The uplifting melody and bright instrumentation make it one of his most feel-good tracks, contrasting with the heartbreak and longing found in many of his earlier works.
Upon its release, “You Got It” became an international success, reaching the top 10 in multiple countries and reintroducing Orbison to a new audience. The song’s warm, reassuring message and Orbison’s effortless vocals made it a fitting farewell to a legendary career.
Decades later, “You Got It” remains a favorite among fans, serving as a reminder of Orbison’s unparalleled talent and his ability to connect with listeners through deeply heartfelt music.
10. Candy Man – 1961
Roy Orbison’s “Candy Man” is a playful, flirtatious tune that showcases a different side of the legendary singer. Released in 1961 as the B-side to “Crying,” the song became a hit in its own right, reaching the top 30 on the Billboard charts.
With its bluesy, almost rockabilly feel, “Candy Man” stands out from Orbison’s usual orchestral ballads. The song’s catchy rhythm, driven by a steady groove and handclaps, gives it an easygoing, danceable quality. The lyrics are lighthearted and fun, using sweet metaphors to describe a charming, irresistible figure who always seems to get what he wants.
While Orbison is best known for his dramatic, operatic vocal performances, “Candy Man” proves that he could also bring a sense of playfulness to his music. The song became a staple of his live performances, where fans loved its upbeat energy.
Though not as emotionally intense as his biggest ballads, “Candy Man” is an essential part of Orbison’s discography, showing his versatility as an artist. It’s a reminder that, beyond the heartbreak and soaring vocals, Orbison also had a knack for delivering pure, feel-good rock and roll.
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.
