Few voices in music history have left as profound an impact as Roy Orbison’s. With his hauntingly beautiful voice, deeply emotional lyrics, and unmistakable melodies, Orbison didn’t just sing songs—he told stories that resonated across generations. Known as “The Caruso of Rock” and “The Big O,” his music has transcended time, touching the hearts of millions and carving a permanent place in classic rock and roll history.
Orbison’s career was nothing short of legendary. From his groundbreaking hits of the 1960s to his astonishing revival in the 1980s, his ability to capture the complexity of human emotions—love, heartbreak, longing, and joy—remains unparalleled. Whether it’s a soul-stirring ballad or an energetic anthem, Orbison’s songs are a testament to his genius as both a songwriter and performer.
In this article, we’re taking a journey through the top 10 most popular Roy Orbison songs of all time. These tracks have not only defined his legacy but have also become timeless classics that continue to inspire and captivate listeners. So grab your sunglasses, turn up the volume, and get ready to relive the magic of Roy Orbison—one unforgettable song at a time!
1. “Oh, Pretty Woman” (1964)
Roy Orbison’s “Oh, Pretty Woman” is one of the most iconic rock and roll songs of all time, a track that defined an era and remains instantly recognizable decades after its 1964 release. Co-written with Bill Dees, the song was inspired by an everyday moment: Orbison’s wife, Claudette, was heading out, and when Orbison asked if she needed money, Dees quipped, “A pretty woman never needs any money.” That offhand remark sparked the creation of a song that perfectly captures the excitement and admiration of seeing a beautiful woman walk by. The song’s opening guitar riff is one of the most famous in rock history, instantly grabbing the listener’s attention before launching into a rhythm that’s impossible to resist. Orbison’s deep, commanding vocals carry an air of both confidence and longing, making the song feel both playful and passionate. Its chart-topping success made Orbison a household name, and its enduring appeal has kept it alive in pop culture through movies, commercials, and covers by other artists. Whether played on the radio, featured in Pretty Woman (1990), or covered by rock legends, “Oh, Pretty Woman” remains a timeless anthem of admiration and desire.
2. “Crying” (1961)
Few songs capture the pain of lost love as powerfully as Roy Orbison’s “Crying.” Released in 1961, this heartbreaking ballad is a showcase of Orbison’s extraordinary vocal range and ability to convey deep emotion. The song begins softly, with a delicate melody and restrained vocals, but as it progresses, Orbison’s voice rises to an emotional crescendo, delivering a performance so raw and passionate that it leaves listeners spellbound. The orchestral arrangement swells alongside his voice, creating an overwhelming sense of sorrow and longing. The lyrics tell the story of a man who thought he had moved on from love, only to break down in tears when confronted with his lingering feelings. It’s a universally relatable theme, and Orbison’s delivery makes it feel deeply personal. Over the years, “Crying” has been covered by numerous artists, including Don McLean and k.d. lang, but none capture the aching vulnerability of Orbison’s original. Inducted into the Grammy Hall of Fame, this song stands as one of Orbison’s most enduring classics, proving that no one could express the depth of heartache quite like him. Even decades later, “Crying” remains an emotional powerhouse that resonates with anyone who has ever loved and lost.
3. “Only the Lonely (Know the Way I Feel)” (1960)
“Only the Lonely (Know the Way I Feel)” was the song that truly put Roy Orbison on the map, marking his breakthrough hit in 1960. Before this song, Orbison had struggled to find his unique sound, but with “Only the Lonely,” he established the signature style that would define his career. The track’s lush orchestration, dramatic vocal delivery, and heartfelt lyrics captured a sense of longing and isolation that struck a chord with listeners. Orbison’s voice soars effortlessly, carrying a sense of vulnerability and yearning that few artists can replicate. The song’s melody is hauntingly beautiful, with a slow, deliberate pace that allows every emotion to fully sink in. The lyrics speak directly to anyone who has ever felt the sting of loneliness, making it deeply relatable. Upon its release, the song quickly climbed the charts, reaching No. 2 on the Billboard Hot 100 and solidifying Orbison’s place as a major force in the music industry. It also influenced future generations of musicians, with legends like Elvis Presley and The Beatles citing Orbison’s unique style as an inspiration. “Only the Lonely” remains one of the defining ballads of the early rock and roll era.
4. “In Dreams” (1963)
Roy Orbison’s “In Dreams,” released in 1963, is a hauntingly beautiful song that transports listeners into a surreal, dreamlike world of love and longing. Unlike traditional pop songs, “In Dreams” doesn’t follow a standard verse-chorus structure; instead, it flows like a narrative, building in intensity as it progresses. The song begins softly, almost like a lullaby, before swelling into a powerful emotional climax. Orbison’s ethereal vocals make the listener feel as though they are floating through the story with him, experiencing every moment of love and loss. The lyrics tell of a man who finds happiness with his love only in dreams, only to wake up and realize she’s gone. This dreamlike quality is reinforced by the lush, cinematic orchestration, making the song feel more like a short film than a typical ballad. Decades after its release, “In Dreams” found new life when it was prominently featured in David Lynch’s 1986 film Blue Velvet, introducing Orbison’s music to a new generation. The song’s eerie, almost hypnotic beauty continues to captivate listeners, making it one of Orbison’s most unique and unforgettable masterpieces.
5. “Blue Bayou” (1963)
“Blue Bayou” is a song that perfectly captures the longing for home and the nostalgia for a simpler, more peaceful life. Released in 1963, the track features one of Roy Orbison’s most heartfelt vocal performances, filled with a sense of wistfulness and hope. The lyrics paint a vivid picture of a tranquil bayou, where life is slow and easy, far away from the worries of the world. Orbison’s voice conveys a deep yearning, making the listener feel every bit of the homesickness expressed in the song. The instrumentation is rich and soothing, with a gentle rhythm that mimics the ebb and flow of the bayou’s waters. Though Orbison’s version was a hit, “Blue Bayou” became even more famous when Linda Ronstadt recorded her own rendition in the 1970s, turning it into an even bigger international success. Despite multiple versions, Orbison’s original remains a timeless classic, filled with emotion and sincerity that only he could deliver. Whether heard on a quiet evening or played during moments of reflection, “Blue Bayou” has an almost magical ability to transport listeners to a place of peace and nostalgia.
6. “You Got It” (1989)
Released in 1989, “You Got It” was a bittersweet moment in Roy Orbison’s career—his triumphant return to the charts, but also one of his final recordings before his untimely passing. Co-written with Jeff Lynne and Tom Petty, the song blends Orbison’s classic vocal style with a modern, upbeat production, creating a track that feels both nostalgic and fresh. The lyrics express unconditional love and devotion, making it one of Orbison’s most uplifting and romantic songs. His voice, still as powerful as ever, soars effortlessly over the melody, reminding listeners why he was one of the greatest singers in music history. “You Got It” became a posthumous hit, reaching the Top 10 in multiple countries and proving that Orbison’s music was timeless. The song introduced his work to a new generation of fans while reaffirming his influence on rock and roll. Its joyful, hopeful energy stands in contrast to some of his more melancholic ballads, showcasing another side of Orbison’s artistry. Though his career was tragically cut short, “You Got It” serves as a fitting farewell—a reminder that his voice and music would live on forever.
7. “It’s Over” (1964)
It’s Over is one of Roy Orbison’s most dramatic and emotionally gripping ballads. Released in 1964, the song is a masterclass in storytelling, vividly capturing the devastation of a love that has come to an end. What sets It’s Over apart is its theatrical arrangement—each verse builds with growing tension, leading up to an overwhelming, almost operatic climax. The orchestration, featuring lush strings and swelling crescendos, enhances the song’s powerful impact.
Orbison’s vocal performance is nothing short of mesmerizing. He begins with a quiet, almost resigned sadness before soaring into heartbreaking wails, perfectly conveying the deep pain of a relationship’s final moments. The lyrics paint a bleak picture of loss, using imagery like “all the rainbows in the sky start to weep and say goodbye,” reinforcing the song’s sense of despair.
When It’s Over was released, it quickly climbed the charts, reaching No. 1 in the UK and solidifying Orbison’s reputation as a master of melancholy. It remains one of his most unforgettable songs, proving that no one could capture the agony of heartbreak quite like him. Even today, It’s Over stands as a testament to the raw emotion and vocal power that defined Orbison’s career.
8. “Running Scared” (1961)
Running Scared is a thrilling, suspenseful love song unlike anything else in Roy Orbison’s catalog. Released in 1961, the song tells the story of a man deeply in love, but afraid that his partner might still have feelings for an old flame. What makes this track so unique is its structure—it starts off slow and steady, with a sense of unease, before gradually building in intensity. There is no chorus, no repeating hook—just a continuous rise in tension, leading up to an unforgettable climax.
The song’s instrumentation follows this same structure, beginning with soft, ominous guitar and gentle backing before swelling into a full orchestral explosion. Orbison’s voice mirrors this progression, growing from quiet worry to a powerful, soaring finale. When he finally belts out the last line, “but you love me,” it’s not just relief—it’s an overwhelming rush of emotion.
This dramatic build-up and cinematic storytelling made Running Scared an instant classic. The song reached No. 1 on the Billboard Hot 100, further cementing Orbison’s status as a musical innovator. Even today, the song remains a masterclass in tension and release, proving that Orbison knew exactly how to captivate an audience.
9. “Dream Baby (How Long Must I Dream)” (1962)
Unlike many of Roy Orbison’s signature heartbreak ballads, Dream Baby (How Long Must I Dream) is an upbeat, infectious tune that highlights a different side of his artistry. Released in 1962, the song is pure rockabilly fun, driven by a lively rhythm and an irresistible melody. It captures the excitement and frustration of longing for someone, making it an instantly relatable love song.
Orbison’s voice, as always, takes center stage, effortlessly gliding through the song’s bouncy verses before soaring into the anthemic chorus. The lyrics are simple but effective, expressing the universal feeling of dreaming about someone special and wishing they would feel the same way. Unlike his more melancholic hits, Dream Baby is filled with playful energy, making it a favorite among fans who enjoy Orbison’s lighter, more carefree side.
The song became a hit upon its release, reaching No. 4 on the Billboard Hot 100. Though it may not be as dramatic as Crying or Only the Lonely, Dream Baby remains an essential part of Orbison’s legacy. It’s a song that makes you tap your feet, sing along, and, most importantly, believe in the power of dreams and love.
10. “Love Hurts” (1961)
Few songs capture the pain of love as simply and effectively as Love Hurts. Originally recorded by The Everly Brothers, Roy Orbison made the song his own in 1961, infusing it with a raw, heartfelt intensity that has made it one of the most enduring heartbreak anthems of all time.
The song explores the idea that love, while beautiful, can also be deeply painful. The lyrics are brutally honest: “Love is like a flame, it burns you when it’s hot.” Orbison’s voice, with its signature emotional depth, brings out every ounce of sorrow and longing in the words. The stripped-down arrangement keeps the focus on the vocals, allowing the song’s emotional weight to fully take hold.
Though Love Hurts has been covered by many artists over the years—including notable versions by Nazareth and Joan Jett—Orbison’s rendition remains one of the most powerful. His ability to convey vulnerability and heartbreak is unmatched, making this song a standout in his vast catalog of emotional ballads. For anyone who has ever experienced the highs and lows of love, Love Hurts is a song that speaks directly to the heart.
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.
