Roy Orbison, the man with the velvet voice and unmatched emotional depth, remains one of the most iconic figures in music history. Known for his soaring vocals, heart-wrenching ballads, and haunting lyrics, Orbison’s songs transcend generations, resonating as deeply today as they did decades ago. His ability to blend vulnerability with power made him a trailblazer, influencing countless artists and cementing his legacy as a pioneer of rock and roll.
But what makes his music truly unforgettable? Is it the way his voice captures raw emotion? Or the way his melodies linger in your soul long after the final note? In this article, we take a journey through the top 10 most popular Roy Orbison songs of all time—timeless masterpieces that continue to captivate audiences around the world. From the aching beauty of “Crying” to the electrifying charm of “Oh, Pretty Woman,” these tracks showcase the genius of a man who turned heartbreak into art and triumph into melody.
Whether you’re a lifelong fan or discovering Orbison’s brilliance for the first time, this list promises to remind you why his music remains an enduring treasure. Dust off your vinyl or queue up your streaming playlist—it’s time to relive the magic!
1. Oh, Pretty Woman (1964)
Roy Orbison’s “Oh, Pretty Woman,” released in 1964, is an enduring rock and roll anthem that has transcended generations. The song’s infectious energy is driven by a catchy, upbeat rhythm and a memorable guitar riff that immediately grabs the listener’s attention. Co-written with Bill Dees, the lyrics tell the story of a man who is mesmerized by a beautiful woman passing by, and his daring desire to get her attention. With Orbison’s unique, soaring vocals, the song blends romance, excitement, and optimism into a timeless pop masterpiece. The way Orbison conveys yearning with his powerful falsetto and rich voice captures the heart of the track. “Oh, Pretty Woman” struck a chord worldwide, reaching number one on the Billboard Hot 100 for three consecutive weeks. Its success didn’t stop there—it became an integral part of pop culture, featured in films, TV shows, and commercials. The track also sparked numerous covers by other artists. What makes “Oh, Pretty Woman” so enduring is its universality; everyone can relate to the experience of seeing someone so captivating that it leaves you breathless. It’s a quintessential pop moment and remains one of Orbison’s most celebrated songs, echoing his legacy as a rock and roll legend.
2. Only the Lonely (1960)
“Only the Lonely,” released in 1960, marked a significant milestone in Roy Orbison’s career, showcasing his ability to express deep emotional vulnerability through music. The song captures the essence of loneliness, as it tells the story of a man suffering from unrequited love. The poignant lyrics, combined with Orbison’s powerful falsetto, create a heart-wrenching sense of despair that resonates with anyone who has experienced loneliness. Orbison’s voice, both tender and intense, brings an authenticity to the song that makes it stand out. His soaring vocals take the listener through the emotional highs and lows of heartbreak, turning the track into a deeply moving experience. “Only the Lonely” is enhanced by its lush orchestration, which gives it a cinematic, almost operatic quality. It became Orbison’s first major hit, peaking at number two on the Billboard Hot 100, and its success solidified his position as a rising star in the music world. The song’s influence can be felt across many artists, with its unmistakable sound being a major inspiration for later generations of musicians. “Only the Lonely” remains a defining moment in Orbison’s career, as it highlighted his exceptional ability to evoke powerful emotions through his unique vocal style.
3. Crying (1961)
Released in 1961, “Crying” is a masterpiece that exemplifies Roy Orbison’s remarkable ability to convey profound emotion through his music. The song tells the story of someone mourning the loss of love and the sorrow of unrequited feelings. Orbison’s vocal delivery in “Crying” is unmatched, as he seamlessly moves between gentle vulnerability and intense passion, capturing the raw emotion of heartbreak. The sweeping orchestral arrangement, with its soaring strings and dramatic flourishes, mirrors the emotional depth of the lyrics, elevating the song into an unforgettable listening experience. Orbison’s rich voice, which could reach both heartbreaking softness and heart-pounding intensity, has become synonymous with the emotional storytelling embedded in his music. “Crying” became an instant classic, achieving success on the Billboard Hot 100, where it reached number two. Over time, it has become one of Orbison’s signature songs, widely covered by artists from multiple genres. Its enduring power lies in its universality—anyone who has ever loved and lost can relate to the feelings of longing and despair that permeate the track. “Crying” stands as a testament to Orbison’s songwriting and vocal prowess, remaining a high point in his illustrious career.
4. Running Scared (1961)
“Running Scared,” released in 1961, is a dramatic and emotionally charged ballad that displays Roy Orbison’s mastery of tension and release. The song tells the story of a man who fears losing the woman he loves to a rival, and his emotions are conveyed through the dramatic shifts in the music. The track starts softly, with a sense of trepidation, as the protagonist nervously contemplates the possibility of heartbreak. As the story unfolds, the music builds to a powerful crescendo, mirroring the character’s growing fear of losing his love. Orbison’s operatic vocal delivery further intensifies the emotional weight of the song, making it feel cinematic in nature. The soaring vocals and dynamic arrangement create a rollercoaster of emotions, pulling the listener into the protagonist’s emotional turmoil. “Running Scared” reached number one on the Billboard Hot 100, thanks to its innovative structure and Orbison’s ability to build suspense. The song’s fusion of storytelling and musical progression made it a standout hit, and it has been widely regarded as one of his finest works. “Running Scared” solidified Orbison’s place in music history, demonstrating his unique ability to create a deep emotional connection with his audience through his distinct vocal style and musical storytelling.
5. In Dreams (1963)
“In Dreams,” released in 1963, is one of Roy Orbison’s most hauntingly beautiful and emotionally complex songs. The track transports listeners into a dreamlike world where love exists only in the realm of the subconscious. Orbison’s voice is angelic as he sings about a love that exists only in his dreams, capturing the bittersweet nature of unattainable love. The lush orchestral arrangement enhances the dreamlike quality of the song, with its sweeping strings and ethereal melodies giving the music a sense of floating in a surreal, otherworldly space. The lyrics and music work together to convey the longing and melancholy of a love that is forever out of reach. “In Dreams” stands apart from many other songs of the era due to its unconventional structure, with the verses flowing seamlessly into one another and the lack of a typical chorus. Its ethereal quality makes it a standout in Orbison’s catalog and ensures its lasting impact. The song achieved moderate commercial success, but it has since gained widespread recognition as one of Orbison’s greatest songs. “In Dreams” has been used in films, most famously in David Lynch’s Blue Velvet, and remains a symbol of Orbison’s unmatched ability to evoke deep emotion through music.
6. Blue Bayou (1963)
“Blue Bayou,” released in 1963, is a haunting and nostalgic ballad that showcases Roy Orbison’s ability to capture the melancholy of longing for a better time. In the song, Orbison sings about the desire to return to a place of comfort and peace, depicted as a serene bayou. The lyrics evoke vivid imagery, with references to the peacefulness of the bayou and the yearning to escape from present sorrow. Orbison’s voice is filled with emotion, conveying the deep longing and yearning the protagonist feels for a simpler time. The orchestral arrangement enhances the song’s reflective mood, with lush strings and subtle instrumentation adding depth to the emotional experience. “Blue Bayou” has become one of Orbison’s most beloved tracks, capturing the universal experience of wanting to return to a happier and more peaceful moment in life. Though it wasn’t one of Orbison’s biggest commercial hits, the song has remained a fan favorite and has been covered by several artists over the years, most famously by Linda Ronstadt in 1977. Ronstadt’s version introduced the song to a new generation of listeners, but it is Orbison’s original performance that remains the definitive rendition. “Blue Bayou” remains a testament to Orbison’s ability to convey deep emotion through his extraordinary voice.
7. Dream Baby (How Long Must I Dream) (1962)
“Dream Baby (How Long Must I Dream),” released in 1962, is an energetic and upbeat pop song that shows a different side of Roy Orbison’s musical versatility. Unlike his more melancholy ballads, this track is lively and full of youthful exuberance. With a catchy melody and a driving rhythm, “Dream Baby” captures the excitement and impatience of being in love and yearning for someone. The song’s lyrics express the longing for a romantic partner, with the protagonist asking how long they must dream about being together. The infectious energy of the track made it an instant hit, reaching the top 10 on the Billboard Hot 100. Orbison’s powerful vocals give the song a sense of urgency and passion, even as the upbeat tempo adds a sense of fun and lightness. “Dream Baby” stands out in Orbison’s catalog for its upbeat vibe, showcasing a more playful side of the artist. Despite its more carefree nature, Orbison’s vocal delivery still carries the emotional weight that he was known for, adding depth to the song. The track remains a beloved part of Orbison’s catalog, showcasing his ability to craft songs that are both fun and emotionally resonant.
8. It’s Over (1964)
“It’s Over,” released in 1964, is one of Roy Orbison’s most emotionally charged ballads, delving deep into the devastation of a love that has ended. The song explores the finality of a broken relationship, with lyrics that express sorrow, despair, and the bitter realization that the relationship is truly over. Orbison’s voice, filled with anguish and raw emotion, perfectly captures the pain of heartache. His powerful vocal delivery, combined with the lush orchestral arrangement, elevates the song to an epic level of emotional intensity. The orchestration, with its sweeping strings and dramatic flourishes, creates a cinematic feeling, making it feel as though the listener is witnessing the end of a relationship firsthand. “It’s Over” was a commercial success, reaching the top 10 on the Billboard Hot 100, and remains one of Orbison’s most beloved tracks. The song’s emotional depth and the vulnerability of Orbison’s performance have made it a classic, and it continues to resonate with audiences who have experienced the pain of lost love. “It’s Over” is a quintessential example of Orbison’s ability to turn heartache into an unforgettable musical experience.
9. You Got It (1989)
“You Got It,” released in 1989, marked Roy Orbison’s triumphant return to the top of the charts after a long hiatus. The song was written by Orbison, Jeff Lynne, and Tom Petty, and it combines Orbison’s classic sound with a more modern pop-rock sensibility, making it appealing to a new generation of listeners. The song’s lyrics celebrate the joy of being in love, with the protagonist declaring that their partner has everything they could ever want. The upbeat, feel-good track was an instant hit, reaching the top 10 on the Billboard Hot 100 and becoming one of Orbison’s biggest successes in the 1980s. “You Got It” also served as a fitting tribute to Orbison’s enduring talent, as it captured his ability to create timeless music that resonates across generations. The song’s catchy melody, uplifting lyrics, and Orbison’s unmistakable voice helped solidify his place in the musical landscape of the late 20th century. Even though Orbison passed away just a few months after the release of the song, “You Got It” became a posthumous hit, introducing his music to a new audience and reaffirming his legacy as a legendary figure in popular music.
10. Ooby Dooby (1956)
“Ooby Dooby,” released in 1956, was Roy Orbison’s first charting single and served as the beginning of his legendary career. The song is a lively, upbeat rockabilly track with a catchy, infectious rhythm that captures the youthful energy of the early rock and roll era. With playful lyrics and a driving beat, “Ooby Dooby” is a fun and energetic song that stands in contrast to the emotional ballads that Orbison would later become famous for. The track’s carefree attitude and rockabilly sound made it a hit, and it introduced Orbison as an exciting new talent in the music world. Though “Ooby Dooby” is somewhat different from Orbison’s later ballads, it is an important part of his musical evolution, showcasing his ability to thrive in various genres. The song was one of the first to highlight Orbison’s unique voice, which would later become synonymous with heartbreak and emotion. “Ooby Dooby” remains a lively reminder of Orbison’s roots in rockabilly music and the energetic spirit of the 1950s rock and roll movement. It marks the start of a career that would go on to redefine popular music, leaving an indelible mark on the industry.
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.
