Roy Orbison, the legendary singer-songwriter known for his haunting voice and emotive ballads, has left an indelible mark on the music world. With a career spanning several decades, his unique blend of rock and roll, pop, and country has captivated audiences across generations. Orbison’s ability to convey deep emotion through his lyrics, paired with his signature sunglasses and enigmatic stage presence, has solidified his status as an iconic figure in music history.
In this article, we delve into the top 10 most popular Roy Orbison songs of all time, celebrating the tracks that have resonated with fans and influenced countless artists. From the soaring melodies of “Oh, Pretty Woman” to the poignant storytelling in “Crying,” each song showcases Orbison’s extraordinary talent and artistry. Whether you’re a lifelong fan or new to his music, prepare to embark on a nostalgic journey through some of the greatest hits that define not just his career, but the very essence of classic rock and pop. Join us as we explore the timeless appeal of Roy Orbison’s music, highlighting the songs that continue to capture hearts and inspire listeners around the world.
1. Oh, Pretty Woman (1964)
Released in 1964, “Oh, Pretty Woman” quickly became one of Roy Orbison’s most iconic hits, a timeless classic that still resonates today. The song’s infectious energy, driven by its upbeat tempo and catchy guitar riff, is the perfect backdrop for Orbison’s soaring vocals. As he sings about spotting a beautiful woman walking down the street, his voice expresses a mixture of desire, awe, and hope. The lyrics themselves are simple, yet they evoke a sense of longing that captures the universal feeling of infatuation. Orbison’s delivery, filled with longing yet tinged with excitement, brings the song to life, making it more than just an observation of a pretty woman but a story of romantic yearning.
The charm of “Oh, Pretty Woman” is in its accessibility—its upbeat nature, infectious chorus, and catchy melody make it easy to sing along to, but it’s Orbison’s unique vocal style that gives the song its staying power. His voice has a vulnerability to it that connects emotionally with the listener, even as he expresses something as simple as admiration for a woman he doesn’t know. The track’s immediate success made it a massive commercial hit, reaching the top of the charts and propelling Orbison into the musical stratosphere. It solidified his place in music history, with the track still appearing in films, commercials, and covers decades later. Orbison’s original version of “Oh, Pretty Woman” remains unrivaled, capturing the magic of the moment in a way no other rendition quite matches.
With its irresistible energy and unforgettable hook, “Oh, Pretty Woman” continues to stand as one of Orbison’s signature songs and an enduring anthem of youthful love and wonder.
2. Crying (1961)
Released in 1961, “Crying” is one of Roy Orbison’s most emotionally charged songs, showcasing his unparalleled ability to convey deep sorrow and vulnerability. The song tells the story of a man heartbroken after his lover has left, and Orbison’s voice, with its powerful emotional depth, conveys the pain of loss in a way few artists can replicate. The haunting melody, which features soaring strings and a lush orchestral arrangement, amplifies the sadness of the lyrics, creating an atmosphere that is both cinematic and intimate. With each note, Orbison’s voice rises to heartbreaking heights, perfectly capturing the torment of a man who still loves someone who no longer feels the same.
The lyrics of “Crying” are simple, but their emotional weight is immense. The narrator pleads for his lost love, lamenting his inability to stop the inevitable. The song builds in intensity as Orbison’s voice rises to a crescendo, making the listener feel every ounce of heartbreak and despair. The dramatic orchestration—complete with sweeping strings and a melodic piano line—creates a cinematic feel, as if the song itself could be the soundtrack to a tragic romance. This emotional depth is what makes “Crying” not just a song, but an experience.
“Crying” marked a high point in Orbison’s career, showcasing his unique talent for blending rock and pop with the emotional richness of balladry. The song’s ability to convey universal feelings of heartbreak and loss, combined with Orbison’s stunning vocal delivery, makes it a timeless piece that resonates just as deeply today as it did when it was first released.
3. Only the Lonely (1960)
“Only the Lonely,” released in 1960, is a pivotal moment in Roy Orbison’s career, marking the beginning of his rise as one of the most distinctive voices in pop and rock music. The song’s poignant lyrics, paired with Orbison’s aching baritone, convey the deep sense of isolation and heartache that comes with unrequited love. The story centers on someone left alone, feeling as though no one else could understand their pain. Orbison’s voice, rich and full of longing, perfectly captures this sense of loneliness, making the song resonate deeply with anyone who has ever experienced the heartbreak of unreturned affection.
The lush orchestration that accompanies “Only the Lonely” heightens the emotional impact of the track, as sweeping strings and dramatic piano melodies create an atmosphere of melancholy and desolation. The arrangement complements Orbison’s voice, which is both tender and filled with raw emotion. His vocal delivery is especially notable for its dynamic range, effortlessly transitioning between vulnerability and powerful intensity, pulling listeners into the emotional core of the song.
“Only the Lonely” is not just a song of sadness but a universal expression of yearning. It’s a track that speaks to anyone who has felt abandoned or isolated, and Orbison’s ability to communicate those feelings in such a deeply emotional way made the song a massive hit. Its haunting melody, paired with its heartfelt lyrics, made it a defining moment in Orbison’s career, laying the groundwork for many more iconic ballads. “Only the Lonely” remains a classic that showcases Orbison’s vocal prowess and his ability to tap into the most profound emotions.
4. In Dreams (1963)
“In Dreams,” released in 1963, is a haunting and ethereal song that showcases Roy Orbison’s remarkable ability to blend dreamlike imagery with deep emotional resonance. The song paints a vivid picture of longing, as the narrator dreams of a lost love, and the accompanying music captures the surreal and fantastical quality of such dreams. Orbison’s voice floats above the melody with a sense of vulnerability and longing, conveying the delicate nature of a dream that feels real but remains unreachable.
The song’s orchestration is as intricate and delicate as the lyrics themselves, with lush strings and a haunting chorus that amplify the otherworldly atmosphere. As Orbison’s voice weaves through the lyrics, it’s as though the listener is transported into a world where dreams and reality blur. The emotional depth of the song is undeniable, with each note filled with yearning and sadness. “In Dreams” is a perfect example of how Orbison could take a simple concept—dreaming of a lost love—and turn it into something profound and moving.
“In Dreams” stands out for its combination of dreamy, almost cinematic production and the heartache that comes with longing for someone who is no longer part of your life. The song’s enduring popularity is a testament to its emotional depth and Orbison’s unparalleled vocal ability. As he sings about the dream of reuniting with a lost love, listeners can’t help but feel the universal pain of desire and loss. It’s a stunning example of Orbison’s artistry and his ability to evoke powerful emotions with both his voice and his music.
5. Running Scared (1961)
“Running Scared,” released in 1961, is a gripping ballad that highlights Roy Orbison’s ability to convey the anxiety and fear that comes with the possibility of losing someone you love. The song’s dramatic crescendo, paired with its lush orchestral arrangement, creates a sense of urgency and tension that mirrors the narrator’s feelings of desperation and panic. Orbison’s emotive delivery brings the song’s intense narrative to life, as he expresses the fear of watching a lover slip away, unable to do anything to stop it.
The song’s tension builds as Orbison’s voice rises, pulling the listener into the emotional turmoil of the situation. His vocal performance is both dynamic and poignant, capturing the shifting emotions of a man who is both terrified and helpless. The orchestration, with its swelling strings and dramatic build, enhances the song’s sense of anxiety, creating a sense of impending loss. “Running Scared” is one of Orbison’s most dramatic songs, and it stands out for its powerful storytelling and intense emotion.
The song was a major commercial success, but its lasting appeal lies in its emotional depth. The fear and desperation captured in “Running Scared” are universal, making it a song that continues to resonate with listeners who have experienced the vulnerability of love and loss. “Running Scared” is a prime example of Orbison’s ability to connect with his audience on a deep, emotional level, making it one of his standout tracks and a classic in his catalog.
6. Blue Angel (1959)
Released in 1959, “Blue Angel” is one of Roy Orbison’s earliest hits, and it provides a glimpse of the raw emotional depth that would later define his career. The track features a gentle yet sorrowful melody that perfectly complements Orbison’s smooth, tender vocals. With lyrics about a love unrequited and a heart broken, “Blue Angel” captures a sense of longing that would become a hallmark of Orbison’s work. His voice, tender and vulnerable, rises and falls with each lyric, conveying a deep sense of sadness and unfulfilled desire.
The orchestration is understated but effective, with soft piano chords and lush strings enhancing the melancholy mood of the song. The delicate arrangement allows Orbison’s voice to shine, showcasing his ability to express emotion through every note. As the song progresses, the listener is drawn into a world of unspoken yearning, where love is unreturned, and the narrator is left alone with his feelings.
“Blue Angel” is a perfect example of Orbison’s early style, combining elements of rock and pop with emotional depth and lyrical sophistication. The track didn’t achieve the same level of commercial success as some of his later hits, but it remains an important part of his discography. It sets the stage for the songs to come, showing that Orbison had an innate ability to convey complex emotions with simplicity and elegance. The song’s enduring charm lies in its vulnerability, which continues to resonate with listeners who have experienced the pain of loving someone who doesn’t love them back.
7. Dream Baby (How Long Must I Dream) (1962)
“Dream Baby (How Long Must I Dream)” is a perfect fusion of Roy Orbison’s signature sound with a catchy, upbeat melody that was perfect for the early ’60s pop scene. Released in 1962, the song is about a man who dreams of a love that he yearns for, but cannot quite attain. The lyrics reflect the pain of waiting for someone to realize how much they mean, while Orbison’s powerful voice conveys the mix of hope and frustration that often accompanies unrequited love.
The track is driven by a bouncy rhythm, with Orbison’s voice rising above the upbeat instrumentation, creating an infectious energy that contrasts with the more somber themes of the lyrics. The upbeat tempo gives the song a lighthearted, almost whimsical quality, while the story behind the lyrics is one of longing and emotional turmoil. This contrast between the music and the sentiment is one of the song’s most endearing qualities, making it a perfect example of Orbison’s ability to balance emotional depth with catchy pop melodies.
“Dream Baby” was a commercial success and solidified Orbison’s position as one of the top artists of the early ’60s. The song’s upbeat rhythm and catchy chorus made it an instant favorite, but its emotional depth ensured that it would resonate with listeners for years to come. It’s a song about yearning and hope, but it’s also an anthem of optimism, as the narrator continues to dream of the love he wishes for. “Dream Baby” is an enduring classic that combines Orbison’s musical artistry with his unique ability to convey emotion through his vocal performance.
8. You Got It (1989)
“You Got It,” released in 1989, marked Roy Orbison’s triumphant return to the music scene after a period of relative obscurity, and it stands as a testament to his timeless appeal and musical versatility. The song is a celebration of love and appreciation, with Orbison singing about someone who has all the qualities he desires. The track is upbeat, smooth, and filled with Orbison’s signature warmth, showcasing his ability to create a feel-good atmosphere while maintaining his trademark emotional depth.
The production of “You Got It” is a departure from the more orchestral arrangements of his earlier work, incorporating a modern rock sound with slick guitar riffs and a more contemporary beat. However, Orbison’s voice remains as powerful and evocative as ever, and his ability to convey sincerity and admiration through his delivery is unmatched. The lyrics express a sense of admiration and awe for a person who has captured the singer’s heart, and Orbison’s rich baritone brings those feelings to life in a way that only he can.
The track was a commercial success, reaching the top of the charts and reaffirming Orbison’s status as a musical legend. “You Got It” is a perfect blend of contemporary production and classic Orbison style, proving that his voice and songwriting were as relevant in the ’80s as they had been in the ’60s. The song’s joyful celebration of love, paired with Orbison’s unparalleled vocal delivery, makes it a highlight of his later career and a beautiful reminder of his enduring legacy in popular music.
9. It’s Over (1964)
“It’s Over,” released in 1964, is one of Roy Orbison’s most dramatic and emotionally charged ballads. The song tells the story of the end of a relationship, capturing the resignation and sadness that accompanies the realization that love has been lost. Orbison’s voice, rich and full of sorrow, perfectly conveys the feeling of finality, as the narrator expresses the pain of knowing that it’s truly over. The lyrics, which describe the aftermath of love, are simple yet incredibly effective in capturing the heartache that comes with the end of a relationship.
The orchestral arrangement adds to the song’s dramatic impact, with sweeping strings and piano melodies that enhance the emotional weight of the lyrics. The track builds in intensity as Orbison’s voice rises, reaching a crescendo of emotion as he delivers the final, heartbreaking lines. The song’s melancholy tone is undeniable, and Orbison’s ability to communicate the pain of love lost is what makes “It’s Over” a timeless classic.
“It’s Over” became another major hit for Orbison, and it remains one of his most beloved tracks. The song’s powerful combination of poignant lyrics, dramatic orchestration, and Orbison’s unrivaled vocal delivery make it one of the definitive songs of his career. It encapsulates the feeling of heartache and loss in a way that only Orbison could, and it has remained a staple in his catalog, continuing to move listeners with its emotional depth and beauty.
10. I Drove All Night (1987)
“I Drove All Night,” released in 1987, is a thrilling track that showcases Roy Orbison’s versatility as an artist, blending rock with powerful storytelling. The song narrates the story of someone driving through the night to be with a loved one, driven by determination and longing. The fast-paced beat and driving rhythm give the track a sense of urgency, mirroring the narrator’s frantic desire to reunite with someone they love. Orbison’s passionate delivery and the energetic instrumentation create an exhilarating listening experience that keeps listeners on the edge of their seats.
The track features a more modern rock sound compared to Orbison’s earlier work, with synthesizers and electric guitars driving the beat. However, Orbison’s voice remains as timeless as ever, filled with emotion and intensity. The lyrics, which speak of the lengths the narrator is willing to go to for love, are delivered with conviction and urgency, making the song a powerful anthem of devotion and determination.
“I Drove All Night” was a commercial success, and it introduced Orbison to a new generation of fans who may not have been familiar with his earlier hits. The song’s combination of modern production and Orbison’s classic vocal style made it a standout track in his later career. It proved that Orbison’s musical legacy could transcend generations, with his voice and storytelling ability remaining just as captivating as they had been in the ’60s. “I Drove All Night” is a thrilling, high-energy track that reaffirms Orbison’s place in music history as one of the greatest vocalists and storytellers of all time.
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.
