Roy Orbison, the iconic “Caruso of Rock,” mesmerized the world with his unmistakable voice, heartfelt lyrics, and timeless melodies. Known for his signature sunglasses, haunting falsetto, and emotional storytelling, Orbison’s music transcended generations and cemented his place as one of the greatest artists of all time. From the heartache of unrequited love to the soaring heights of romantic bliss, his songs captured the full spectrum of human emotion, making them unforgettable to listeners worldwide.
In this article, we’ll dive into the top 10 most popular Roy Orbison songs of all time—tracks that have stood the test of time and continue to resonate with fans decades after their release. Whether you’re a lifelong devotee or just discovering the magic of “The Big O,” this list will take you on a journey through Orbison’s extraordinary catalog. These songs are more than just hits; they’re masterpieces that defined an era, inspired countless artists, and remain as powerful today as when they first graced the airwaves. So, grab your headphones and prepare to be immersed in the timeless genius of Roy Orbison—let’s explore the classics that made his voice a legend and his music eternal.
1. “Oh, Pretty Woman” (1964)
“Oh, Pretty Woman” is one of Roy Orbison’s most enduring and recognizable songs, a track that catapulted him into legendary status. Released in 1964, the song immediately struck a chord with audiences thanks to its infectious guitar riff, playful lyrics, and Orbison’s powerful vocal performance. It tells the story of a man who sees a stunning woman walking down the street and is instantly mesmerized by her beauty, capturing the feeling of love at first sight with an upbeat and energetic delivery.
The song’s signature opening guitar lick and driving rhythm give it an electrifying quality that makes it instantly memorable. Orbison’s dynamic vocals seamlessly shift between smooth admiration and desperate longing, adding layers of emotion to what could have been just a simple pop tune. Lyrically, the song walks a fine line between confidence and vulnerability, as the narrator hopes that the woman he desires will notice him.
“Oh, Pretty Woman” became a massive international hit, topping the charts in multiple countries, including the U.S. and the U.K. Over the decades, it has remained a staple of popular culture, appearing in films, commercials, and cover versions by various artists. It stands as a testament to Orbison’s unique ability to blend rock, pop, and emotional storytelling into an unforgettable classic.
2. “Crying” (1961)
Few songs capture the raw pain of heartbreak as effectively as “Crying.” Released in 1961, this ballad is a masterclass in emotional storytelling, with Roy Orbison delivering one of his most powerful and moving vocal performances. The song chronicles the deep sadness of losing a loved one, with the narrator reflecting on how he once tried to hide his tears, only to realize that he is still deeply affected by the loss.
What sets “Crying” apart is Orbison’s ability to build the song’s emotional intensity as it progresses. Starting with a gentle, sorrowful melody, the song gradually rises to a breathtaking crescendo, showcasing his incredible vocal range. His soaring falsetto, combined with the lush orchestration, creates a dramatic and almost cinematic experience that leaves listeners captivated.
The song became an instant classic, reaching No. 2 on the Billboard Hot 100 and cementing Orbison’s reputation as a master of heartbreak ballads. It has since been covered by numerous artists, including Don McLean and k.d. lang, proving its timeless appeal. “Crying” remains one of Orbison’s most iconic and emotionally charged songs, resonating with anyone who has ever experienced the pain of lost love.
3. “In Dreams” (1963)
“In Dreams” is a hauntingly beautiful song that takes listeners on a surreal journey through love and longing. Released in 1963, the song’s dreamlike structure and cinematic quality set it apart from traditional pop ballads. Rather than following a standard verse-chorus format, “In Dreams” unfolds like a story, with each section flowing seamlessly into the next, mirroring the way dreams shift unpredictably.
The lyrics tell the story of a man who experiences a perfect romance in his dreams, only to wake up and realize it was all an illusion. This bittersweet theme, combined with Orbison’s ethereal falsetto and the song’s lush orchestration, creates an atmosphere of deep yearning and melancholy. The contrast between the song’s gentle verses and its dramatic crescendos adds to its emotional impact, making it one of Orbison’s most compelling performances.
“In Dreams” gained even greater recognition when it was prominently featured in David Lynch’s film Blue Velvet (1986), introducing the song to a new generation. Its eerie beauty and deeply personal lyrics continue to resonate with listeners, solidifying its place as one of Orbison’s most unique and unforgettable compositions.
4. “Only the Lonely” (1960)
“Only the Lonely” was the song that truly launched Roy Orbison into stardom, establishing him as a master of heartbreak ballads. Released in 1960, the track features Orbison’s signature blend of operatic vocals, dramatic orchestration, and deeply emotional lyrics. The song speaks to the pain of loneliness and unrequited love, with Orbison’s voice soaring over a lush musical arrangement that accentuates the sense of longing and despair.
Unlike many of the upbeat rock ‘n’ roll hits of the time, “Only the Lonely” introduced a more melancholic, orchestral sound that would become Orbison’s trademark. His ability to convey deep emotion through his vocals was unparalleled, making the listener feel every ounce of sorrow embedded in the lyrics. The song builds gradually, moving from a quiet lament to a full-fledged, heart-wrenching crescendo, showcasing Orbison’s remarkable range and control.
The song was a major commercial success, reaching No. 2 on the Billboard Hot 100 and No. 1 in the U.K. It became one of Orbison’s defining tracks, setting the stage for his future ballads of love and loss. Even decades later, “Only the Lonely” remains a powerful anthem for anyone who has ever felt the sting of loneliness.
5. “Blue Bayou” (1963)
A wistful and evocative ballad, “Blue Bayou” captures a deep sense of nostalgia and longing for home. Released in 1963, the song tells the story of someone dreaming of returning to a peaceful and simpler life on the bayou, away from the struggles of the modern world. Orbison’s rich, velvety vocals lend a sense of warmth and sincerity to the song, making it one of his most beloved recordings.
The melody is both soothing and melancholic, carried by a gentle rhythm and a beautiful blend of country and pop influences. The lyrics paint a vivid picture of a tranquil paradise, where the protagonist imagines reuniting with loved ones and escaping from the sorrows of everyday life. This theme of yearning for a lost past resonated with many listeners, giving the song a timeless quality.
Though Orbison’s version was a hit, “Blue Bayou” gained even greater recognition when Linda Ronstadt covered it in 1977, turning it into one of her biggest hits. Regardless of the version, the song remains a touching and heartfelt tribute to the idea of home and the emotions tied to it, proving the universal appeal of Orbison’s songwriting.
6. “You Got It” (1989)
Released just months before his passing, “You Got It” became one of Roy Orbison’s most significant posthumous hits. Co-written with Tom Petty and Jeff Lynne of the Traveling Wilburys, the song marked a triumphant return for Orbison, blending his classic sound with a more contemporary pop-rock feel. It served as a reminder of his timeless voice and unparalleled ability to craft deeply emotional yet accessible songs.
Unlike his more melancholic ballads, “You Got It” carries a hopeful and uplifting message about unconditional love and devotion. The song’s upbeat tempo, catchy melody, and Orbison’s signature soaring vocals make it instantly memorable. His delivery is filled with warmth and sincerity, giving the lyrics an authenticity that resonates with listeners.
After its release, “You Got It” became a major hit, reaching the Top 10 on the Billboard Hot 100 and topping the charts in multiple countries. The song’s success reaffirmed Orbison’s enduring influence on music and introduced his work to a new generation. Even today, “You Got It” remains a beloved classic, a fitting final gift from one of the greatest voices in rock and roll history.
7. “It’s Over” (1964)
“It’s Over” is a dramatic and emotionally charged ballad that showcases Roy Orbison’s ability to convey the heartbreak of lost love. Released in 1964, the song tells the story of a relationship’s painful end, with the narrator coming to terms with the finality of his heartbreak. The lyrics are stark and unrelenting, repeating the phrase “It’s over” as if to drive home the painful reality.
What sets this song apart is its theatrical build-up. Orbison starts with a soft, almost whispered delivery, gradually escalating into powerful, operatic peaks that send chills down the listener’s spine. His voice, filled with both sorrow and resignation, carries the weight of the song’s despair, making it one of his most emotionally intense performances. The orchestral arrangement further amplifies the song’s drama, adding to its haunting beauty.
The song was a major success, reaching No. 1 in the U.K. and No. 9 in the U.S. Over the years, it has remained one of Orbison’s most compelling ballads, a testament to his unmatched ability to turn heartbreak into art. Few songs capture the finality of lost love as powerfully as “It’s Over.”
8. “Running Scared” (1961)
“Running Scared” is one of Roy Orbison’s most thrilling and suspenseful songs, structured more like a short film than a typical pop track. Released in 1961, the song tells the story of a man in a state of emotional turmoil, fearing that his lover will leave him for someone from her past. What makes the song unique is its relentless build-up—there is no chorus, only a steady, dramatic ascent that keeps the listener on edge.
The tension in the song is palpable, with the instrumentation growing in intensity as the story unfolds. Orbison’s vocals start low and controlled but gradually rise to a breathtaking climax, making for one of his most memorable vocal performances. When the song finally reaches its resolution—where the protagonist’s fears are relieved—it delivers one of the most satisfying payoffs in Orbison’s entire catalog.
“Running Scared” became a No. 1 hit in the U.S. and remains a testament to Orbison’s storytelling prowess. The song’s ability to create suspense and evoke strong emotions makes it stand out as one of his most innovative and impactful compositions.
9. “Dream Baby (How Long Must I Dream)” (1962)
“Dream Baby (How Long Must I Dream)” is one of Roy Orbison’s more upbeat and playful songs, showcasing his versatility as an artist. Released in 1962, the song stands in contrast to his more melancholic ballads, offering a lively and infectious melody that captures the excitement of longing for love. With its steady rhythm, catchy hooks, and Orbison’s signature smooth vocals, “Dream Baby” became an instant favorite among fans.
The song’s lyrics express a deep yearning for love, with the narrator dreaming about a romantic partner who seems just out of reach. The repetition of the phrase “How long must I dream?” emphasizes the protagonist’s impatience and desire, making the song relatable to anyone who has ever pined for someone. Orbison’s delivery is both lighthearted and passionate, creating a perfect balance of energy and emotion.
Upon its release, “Dream Baby” climbed the charts, reaching No. 4 on the Billboard Hot 100. Its infectious groove and feel-good energy made it a popular radio hit, proving that Orbison could craft songs beyond his signature dramatic ballads. Over the years, the song has been covered by numerous artists, but Orbison’s version remains the definitive take.
10. “Love Hurts” (1961)
Roy Orbison’s rendition of “Love Hurts” is one of the most poignant interpretations of heartbreak ever recorded. Originally written by Felice and Boudleaux Bryant, the song was first recorded by The Everly Brothers, but Orbison’s version gave it a raw emotional depth that resonated deeply with audiences. Released in 1961 as part of his album Roy Orbison Sings Lonely and Blue, the track showcases his ability to turn simple lyrics into a deeply moving experience.
Orbison’s vocals are hauntingly beautiful, carrying a mix of tenderness and pain that perfectly encapsulates the bittersweet nature of love. The song describes the inevitable pain that comes with love and loss, making it one of the most universally relatable songs in his catalog. His delivery, combined with the song’s gentle instrumentation, creates an atmosphere of quiet sorrow, making it stand out even among his other ballads.
Though it wasn’t initially a major hit, “Love Hurts” went on to become one of Orbison’s most enduring classics, covered by artists like Nazareth, Gram Parsons, and Emmylou Harris. His version remains one of the most heartfelt and definitive, proving that few could capture heartache as beautifully as Roy Orbison.
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.
