20 Best Roy Orbison Songs of All Time

20 Best Roy Orbison Songs of All Time featured image

Known as “The Big O” and “The Caruso of Rock,” Roy Orbison stands as one of the most influential voices in rock and roll history. His three-octave vocal range, combined with emotionally charged ballads and a distinctive operatic style, created a sound that transcended generations and continues to inspire musicians today. From his early rockabilly roots at Sun Records to his triumphant comeback with the Traveling Wilburys, Orbison’s catalog remains a testament to his extraordinary talent and enduring legacy.

Oh, Pretty Woman

This iconic 1964 single represents Roy Orbison’s crowning achievement and his biggest commercial success worldwide. Co-written with Bill Dees, the song spent three weeks at number one on the Billboard Hot 100 and sold approximately seven million copies globally, making it one of the best-selling singles of its era. The distinctive opening guitar riff, combined with Orbison’s powerful vocals, created an instantly recognizable sound that has been featured in countless films and television shows over the decades. The song’s universal appeal transcends generational boundaries, maintaining its status as a rock and roll standard that continues to resonate with audiences today. Orbison later won a Grammy Award for Best Male Pop Vocal Performance for his live rendition during the HBO special “Roy Orbison and Friends: A Black and White Night,” proving the song’s lasting impact on popular music.

Only the Lonely

Released in 1960 as Orbison’s breakthrough hit with Monument Records, this haunting ballad soared to number two in the United States and claimed the top spot in the United Kingdom. The song showcases Orbison’s ability to convey raw vulnerability and heartbreak through his operatic vocal style, establishing the emotional depth that would become his trademark. Producer Fred Foster’s innovative arrangement complemented Orbison’s soaring voice perfectly, creating a dramatic soundscape that was revolutionary for early 1960s pop music. The track’s success launched Orbison into international stardom and demonstrated that male artists could embrace emotional vulnerability in their music. Many music historians consider “Only the Lonely” as one of the greatest ballads ever recorded, citing its influence on generations of singer-songwriters who followed in Orbison’s footsteps.

Crying

This 1961 masterpiece exemplifies everything that made Roy Orbison a legendary vocalist and songwriter. Co-written with Joe Melson, the song builds from a gentle opening to an emotional crescendo that showcases Orbison’s remarkable three-octave range and his ability to convey profound heartache. The dramatic arrangement features sweeping strings and a memorable melody that perfectly complements the lyrics about lost love and lingering pain. “Crying” became one of Orbison’s signature songs and has been covered by numerous artists including k.d. lang, whose 1992 duet with Orbison won a Grammy Award. The song’s enduring popularity demonstrates how Orbison’s honest emotional expression connected with listeners across different eras, cementing his reputation as one of rock music’s most powerful vocalists.

In Dreams

Written entirely by Roy Orbison in 1963, this ethereal ballad showcases his gift for creating dreamlike soundscapes that blur the lines between reality and fantasy. The song came to Orbison when he was half-awake, and he wrote it in just twenty minutes the following morning, capturing a sense of otherworldly longing that became one of his most distinctive compositions. Its unconventional structure, which forgoes a traditional chorus, demonstrated Orbison’s willingness to experiment with song form while maintaining commercial appeal. The track gained renewed prominence when director David Lynch featured it prominently in his 1986 film “Blue Velvet,” introducing Orbison’s work to a new generation of fans. “In Dreams” was also a regular part of Orbison’s setlist during his 1963 tour with The Beatles, where he consistently received standing ovations from audiences captivated by its haunting beauty.

Blue Bayou

Recorded in 1961 and reaching number three in the UK charts, this melancholic ballad captures the essence of homesickness and nostalgia with poetic imagery. Co-written by Orbison and Joe Melson, the song paints a vivid picture of longing for a peaceful Louisiana setting, demonstrating Orbison’s storytelling abilities beyond simple love songs. The track achieved even greater commercial success when Linda Ronstadt covered it in 1977, taking her version into the top five and making it one of her signature songs. Both versions showcase the song’s timeless melody and universal themes of yearning for simpler times and places. The contrast between Orbison’s operatic delivery and Ronstadt’s country-influenced interpretation demonstrates the song’s versatility and enduring appeal across multiple genres.

Running Scared

This 1961 million-selling single topped the US Billboard Hot 100 and showcased Roy Orbison’s ability to build tension through both vocal performance and arrangement. Written by Orbison and Joe Melson, the song tells the story of a man afraid his girlfriend’s former lover will return and steal her away, a narrative that unfolds with mounting dramatic intensity. The unique ascending melody builds continuously throughout the song without a traditional chorus, culminating in a powerful vocal climax that demonstrated Orbison’s exceptional range and control. The track has been covered by numerous artists including Glen Campbell, Nick Cave and the Bad Seeds, and Del Shannon, each bringing their own interpretation to Orbison’s original vision. “Running Scared” was even played at legendary BBC DJ John Peel’s funeral, testament to its profound emotional impact and cultural significance.

Dream Baby

Originally written by Cindy Walker, this upbeat 1962 single reached number four in the United States and number two in the United Kingdom, becoming one of Orbison’s most commercially successful recordings. The song showcases a more energetic side of Orbison’s artistry, proving he could excel at uptempo rock and roll as well as his trademark ballads. Glen Campbell and Lacy J. Dalton both released charting covers of the song, while The Beatles recorded their own version during their first BBC session for the “Teenager’s Turn” show in 1962. Paul McCartney’s performance on that bootleg recording demonstrates the profound influence Orbison had on the Fab Four during rock and roll’s formative years. The song’s infectious melody and driving rhythm make it a perfect showcase for Orbison’s versatility as a performer beyond his more well-known dramatic ballads.

You Got It

Co-written with Traveling Wilburys bandmates Jeff Lynne and Tom Petty, this 1989 single became Orbison’s first top ten hit in the United States in 25 years. Released posthumously as the opening track from his “Mystery Girl” album just one month after his death in December 1988, the song reached number nine in the US and climbed to number three in the UK. The track represented the culmination of Orbison’s late-career resurgence and proved he could still create contemporary hits while maintaining his distinctive vocal style. The bittersweet timing of its release added poignancy to lyrics about finding true love, making it both a celebration of Orbison’s talent and a reminder of his tragic early passing. “You Got It” introduced Roy Orbison to a new generation of fans who may have known him primarily from his Traveling Wilburys work, ensuring his legacy would extend well beyond his 1960s heyday.

I Drove All Night

Written specifically for Roy Orbison by Billy Steinberg and Tom Kelly in 1987, this song has a unique history in popular music. Although Cyndi Lauper released her version first in 1989 and scored a top ten hit with it, Orbison’s original recording from 1987 wasn’t released until 1992, several years after his passing. The Jeff Lynne remix of Orbison’s version reached number seven in the UK, demonstrating the enduring power of his vocal performance even years after his death. The song’s accompanying music video featured actors Jason Priestley and Jennifer Connelly, bringing a cinematic quality that matched the dramatic intensity of Orbison’s interpretation. Recent releases have included the track on various compilations, including a 2017 version with The Royal Philharmonic Orchestra that featured UK country duo Ward Thomas, keeping the song relevant for contemporary audiences.

Handle with Care

As a member of the supergroup Traveling Wilburys alongside George Harrison, Bob Dylan, Tom Petty, and Jeff Lynne, Orbison contributed vocals to this collaborative masterpiece. The song, credited to all members of the group, featured Orbison sharing lead vocal duties with Harrison and Dylan, creating a unique blend of legendary voices. Released as the opening track on “Traveling Wilburys Vol. 1” in 1988, it reached number 45 in the US and number 21 in the UK, introducing Orbison to fans who may not have been familiar with his earlier solo work. The Wilburys project represented a joyful late-career collaboration that allowed Orbison to work with musicians who deeply respected his artistry and influence on rock and roll. Tragically, Orbison passed away just weeks after the album’s release, making this one of his final recorded performances and a testament to his enduring creativity.

It’s Over

This 1964 dramatic ballad showcases Roy Orbison at the peak of his emotional vocal powers, delivering a performance that builds from quiet resignation to powerful heartbreak. The song’s sweeping orchestral arrangement and Orbison’s operatic delivery created a cinematic quality that distinguished his work from other rock and roll artists of the era. Reaching number nine on the Billboard Hot 100 and achieving even greater success internationally, particularly in the UK where it topped the charts, the track demonstrated Orbison’s global appeal. The song’s structure follows Orbison’s preference for dramatic builds and emotional crescendos, techniques that influenced countless balladeers who followed. “It’s Over” remains one of the most requested songs at Orbison tribute shows and continues to demonstrate why he earned the nickname “The Caruso of Rock” for his classical vocal approach to popular music.

Mean Woman Blues

This rocking 1963 cover of a Claude Demetrius song allowed Orbison to showcase his rockabilly roots and prove he could deliver energetic uptempo numbers with the same conviction as his ballads. The track provides a welcome contrast to the predominantly melancholic mood of his greatest hits compilations, demonstrating the versatility that made him such a complete performer. Orbison’s version features his distinctive vocal style applied to a driving rock and roll arrangement, creating a sound that bridges his Sun Records rockabilly past with his Monument Records sophistication. The song has become a favorite among musicians looking to inject energy into Orbison tribute performances and remains a testament to his range as an artist. While not as commercially successful as his ballads, “Mean Woman Blues” proves that Orbison could command attention and showcase his vocal prowess across multiple musical styles.

Candy Man

Featured on various greatest hits compilations including his 1962 collection, this upbeat track from Roy Orbison’s early Monument Records period demonstrates his ability to deliver infectious pop melodies. The song showcases a lighter, more playful side of Orbison’s artistry that contrasts with his more famous dramatic ballads, proving his versatility as a recording artist. With its catchy hook and memorable melody, “Candy Man” became a favorite on oldies radio and continues to appear on comprehensive Orbison anthologies. The track represents the diverse musical palette Orbison explored during his most productive recording years in the early 1960s. While perhaps overshadowed by his more dramatic works, songs like “Candy Man” demonstrate why Orbison was considered one of the most complete artists of his generation.

Blue Angel

This 1960 single represents one of Orbison’s early successes with Monument Records, showcasing the emotional vulnerability that would define his career. The song tells the story of a guardian angel who can provide spiritual comfort but cannot offer the physical presence the narrator desperately craves, a theme of unattainable love that runs through much of Orbison’s work. Its melancholic tone and sweeping arrangement demonstrated Orbison’s ability to create deeply affecting ballads that resonated with audiences experiencing their own heartbreak. The track helped establish the template for Orbison’s signature sound, combining his operatic vocal delivery with sophisticated production values that elevated rock and roll into art. “Blue Angel” remains a beloved deep cut among Orbison devotees and continues to showcase his ability to convey complex emotions through relatively simple lyrical imagery.

Ooby Dooby

Roy Orbison’s first charting single, recorded in 1956 at Sun Records under legendary producer Sam Phillips, marked his entry into professional music. This energetic rockabilly number peaked at number 59 on the Billboard Hot 100 and showcased a completely different side of Orbison before he developed his signature ballad style. The song features the raw, driving energy characteristic of Sun Records’ early rock and roll output, placing Orbison alongside label mates like Elvis Presley, Johnny Cash, and Jerry Lee Lewis. In 1987, Orbison re-recorded “Ooby Dooby” as part of a promotional campaign, and the blended version of both recordings appeared on “The Very Best of Roy Orbison” compilation. The track serves as an important historical document of Orbison’s evolution from a rockabilly performer to one of popular music’s most sophisticated vocalists.

California Blue

From Orbison’s later career, this sophisticated ballad demonstrates that his vocal powers and songwriting abilities remained strong decades after his initial success. Featured on various compilations including “The Very Best of Roy Orbison” and “The Ultimate Collection,” the song showcases the mature artistry Orbison developed over his long career. The track’s production values reflect a more contemporary sound while maintaining the emotional depth that characterized his earlier work, proving Orbison could adapt to changing musical landscapes. “California Blue” represents the bridge between Orbison’s classic 1960s recordings and his late 1980s comeback period, demonstrating consistency in quality throughout his entire career. The song remains a favorite among serious Orbison collectors who appreciate the full breadth of his artistic evolution.

Penny Arcade

This upbeat 1969 single marked one of Orbison’s final chart successes before his career resurgence in the late 1980s. The song features a carnival-like arrangement that contrasts with his dramatic ballads, showcasing Orbison’s willingness to experiment with different musical styles and production approaches. While not as commercially successful as his early 1960s hits, “Penny Arcade” demonstrated that Orbison remained a vital creative force even during a period when his popularity had waned in the United States. The track has been featured on various compilations including “The Big O” collection from 1970, ensuring it remains accessible to new generations of listeners. “Penny Arcade” represents an often-overlooked period of Orbison’s career when he continued to create quality music despite changing musical fashions.

End of the Line

As part of the Traveling Wilburys’ second release, this song holds particular poignancy as it was completed after Roy Orbison’s death in December 1988. The music video features an empty rocking chair and guitar representing Orbison’s presence, serving as a tribute to the late singer’s contributions to the supergroup. The song’s themes of mortality and legacy take on additional meaning given Orbison’s passing, making it both a celebration of life and a meditation on death. Bandmates George Harrison, Bob Dylan, Tom Petty, and Jeff Lynne ensured Orbison’s vocals from earlier sessions were prominently featured, honoring his memory and contributions to their collaborative work. “End of the Line” stands as a fitting final statement from one of rock and roll’s most distinctive voices.

Not Alone Anymore

Featured on the Traveling Wilburys’ first album, this track showcases Roy Orbison’s ability to blend his distinctive voice with the collaborative spirit of the supergroup. The song demonstrated that even in a group featuring rock legends, Orbison’s operatic vocal style remained instantly recognizable and added unique depth to the ensemble sound. Released during Orbison’s triumphant late-career comeback, “Not Alone Anymore” introduced his artistry to younger listeners who may have been unfamiliar with his extensive 1960s catalog. The track’s production by Jeff Lynne, who would also produce Orbison’s final solo album “Mystery Girl,” created a contemporary sound while respecting Orbison’s classical vocal approach. “Not Alone Anymore” remains a testament to Orbison’s ability to collaborate effectively while maintaining his artistic identity.

She’s a Mystery to Me

Written by U2’s Bono and The Edge specifically for Roy Orbison, this haunting ballad appeared on the posthumously released “Mystery Girl” album in 1989. The song demonstrates how younger artists revered Orbison and sought to write material worthy of his extraordinary vocal talents, resulting in one of his most sophisticated late-career recordings. The track’s moody atmosphere and enigmatic lyrics provided the perfect vehicle for Orbison’s dramatic vocal delivery, proving he remained at the peak of his interpretive powers until the end. Jeff Lynne’s production gave the song a contemporary edge while preserving the timeless quality that characterized Orbison’s best work. “She’s a Mystery to Me” stands as evidence that Orbison’s artistry was experiencing a genuine renaissance before his untimely death cut short what promised to be a remarkable final chapter.

Frequently Asked Questions

What was Roy Orbison’s biggest hit song?

“Oh, Pretty Woman” stands as Roy Orbison’s most commercially successful single, reaching number one on the Billboard Hot 100 in 1964 and selling approximately seven million copies worldwide. The song spent three weeks at the top of the charts and became his signature composition, earning recognition as one of rock and roll’s most iconic recordings. The track’s distinctive opening guitar riff remains one of the most recognizable in popular music history, and the song continues to generate substantial royalties decades after its release.

Why did Roy Orbison always wear sunglasses?

Roy Orbison began wearing his trademark dark sunglasses after accidentally leaving his regular prescription glasses on an airplane in 1963, forcing him to wear his prescription sunglasses on stage. The sunglasses became part of his mysterious stage persona, adding to his enigmatic image and distinguishing him visually from other performers of the era. The iconic look became so associated with Orbison that he continued wearing sunglasses throughout his career, creating one of rock music’s most recognizable visual signatures that influenced countless artists who followed.

What happened to Roy Orbison’s family?

Roy Orbison experienced profound personal tragedy when his first wife Claudette died in a motorcycle accident in 1966, followed by the deaths of two of his three sons in a house fire in 1968. These devastating losses occurred during a period when his career was also declining, contributing to years of personal and professional struggle. He found happiness again when he married Barbara Anne Marie Willhonnen Jacobs in 1969, with whom he had two more sons, and together they built a new life in Hendersonville, Tennessee.

How many octaves could Roy Orbison sing?

Roy Orbison possessed a remarkable three-octave vocal range that allowed him to move effortlessly from deep baritone notes to soaring tenor passages, setting him apart from his contemporaries. His operatic approach to rock and roll singing, combined with his exceptional breath control, enabled him to sustain long notes and build dramatic crescendos that became his trademark. Even Elvis Presley, himself a legendary vocalist, called Orbison the finest singer in the world, acknowledging the technical superiority and emotional power of Orbison’s voice.

What was the Traveling Wilburys?

The Traveling Wilburys was a supergroup formed in 1988 consisting of Roy Orbison, George Harrison, Bob Dylan, Tom Petty, and Jeff Lynne, representing one of rock music’s most impressive collaborations. The group released their first album “Traveling Wilburys Vol. 1” to critical and commercial success, with songs like “Handle with Care” and “End of the Line” becoming radio staples. Tragically, Roy Orbison passed away in December 1988, just weeks after the album’s release, making it both a triumphant comeback and a poignant final statement from one of rock’s greatest voices.

Are there any new Roy Orbison releases?

Yes, Roy Orbison’s legacy continues through various releases managed by his sons through Roy’s Boys LLC, including the 2024 compilation “A Cat Called Domino: Rare Cuts from Roy” featuring previously unreleased recordings. The 2023 remastered box set “Roy Orbison: The MGM Years” provided comprehensive documentation of his work during that period, while the 2017 release with The Royal Philharmonic Orchestra reimagined his classics with full orchestral backing. Additionally, holographic concert tours have brought Orbison’s performances to new audiences using advanced technology, ensuring his music continues to reach contemporary listeners. For more information about his timeless catalog, you can explore various songs that showcase his influence on popular music.

How did Roy Orbison influence modern music?

Roy Orbison’s willingness to show emotional vulnerability in his performances opened doors for countless artists to express authentic feelings through their music without fear of appearing weak or unmasculine. His operatic approach to rock and roll demonstrated that popular music could incorporate sophisticated vocal techniques and complex arrangements while maintaining commercial appeal. Artists ranging from Bruce Springsteen to Chris Isaak have cited Orbison as a major influence, with his impact visible in everything from power ballads to alternative rock. When discussing audio equipment that does justice to Orbison’s complex vocal recordings, music enthusiasts often compare headphones to find models that accurately reproduce his remarkable three-octave range.

What makes Roy Orbison’s voice so distinctive?

Beyond his three-octave range, Orbison’s voice possessed a unique timbral quality that combined baritone warmth with tenor brightness, creating a sound that was instantly recognizable. His classical vocal training influenced his approach to phrasing and breath control, allowing him to sustain notes longer than most rock and roll singers and build dramatic crescendos that heightened emotional impact. The vulnerability and sincerity in his delivery made even the most dramatic performances feel authentic rather than overwrought, connecting with listeners on a profound emotional level. For audiophiles seeking to experience the full richness of Orbison’s recordings, many compare earbuds to find options that capture every nuance of his extraordinary vocal performances.

Author: Kat Quirante

- Acoustic and Content Expert

Kat Quirante is an audio testing specialist and lead reviewer for GlobalMusicVibe.com. Combining her formal training in acoustics with over a decade as a dedicated musician and song historian, Kat is adept at evaluating gear from both the technical and artistic perspectives. She is the site's primary authority on the full spectrum of personal audio, including earbuds, noise-cancelling headphones, and bookshelf speakers, demanding clarity and accurate sound reproduction in every test. As an accomplished songwriter and guitar enthusiast, Kat also crafts inspiring music guides that fuse theory with practical application. Her goal is to ensure readers not only hear the music but truly feel the vibe.

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