Buddy Holly, a name etched into the very fabric of rock ‘n’ roll history, left an indelible mark on music in a tragically short career. With his iconic horn-rimmed glasses, boyish charm, and trailblazing spirit, Holly revolutionized the sound of the 1950s, becoming one of the first artists to write, produce, and perform his own music. His unique fusion of rockabilly, country, and rhythm & blues birthed a sound that inspired legends like The Beatles, Bob Dylan, and countless others.
Though his life ended too soon in the infamous “Day the Music Died” plane crash, Buddy Holly’s influence lives on through his timeless hits. From irresistible toe-tappers to heartfelt ballads, his music transcends generations, capturing the raw emotion and youthful energy of a golden era. Whether you’re a lifelong fan or discovering his genius for the first time, these songs will remind you why Buddy Holly remains a cornerstone of rock history.
In this article, we’ll count down the top 10 most popular Buddy Holly songs of all time—a collection of tracks that continue to resonate, proving that great music truly never fades away. Get ready to rediscover the magic of Buddy Holly!
1. “That’ll Be the Day” (1957)
Few songs in rock and roll history are as iconic as “That’ll Be the Day.” Released in 1957, this track was Buddy Holly’s breakthrough hit, establishing him as a pioneer of the genre. The song’s title was inspired by John Wayne’s famous catchphrase in The Searchers, where he delivered the line with his signature tough-guy attitude. Holly and his band, The Crickets, took that phrase and transformed it into a swaggering, confident anthem of love and defiance.
From the very first guitar strum, “That’ll Be the Day” pulls listeners in with its infectious rhythm and catchy melody. Holly’s distinct vocal delivery—marked by his signature hiccup—gives the song its unmistakable charm. The lyrics tell the story of someone who refuses to believe their love will ever walk away, stating, “That’ll be the day when I die.” There’s a playful, almost teasing tone to the words, making the heartbreak feel more like a challenge than a lament.
The song’s energy and attitude resonated with the rebellious youth of the 1950s, helping it skyrocket to No. 1 on the charts. It went on to influence countless musicians, including The Beatles, who cited Holly as a major inspiration. Decades later, “That’ll Be the Day” remains one of the defining songs of early rock and roll, a testament to Buddy Holly’s enduring legacy.
2. “Peggy Sue” (1957)
“Peggy Sue” is one of Buddy Holly’s most instantly recognizable songs, a hypnotic love ballad with a pulsating rhythm that captures the heart of rock and roll. Released in 1957, this track showcased Holly’s ability to blend romance with a driving beat, creating a song that was both tender and energetic.
The song’s signature feature is its rolling drum beat, played by Jerry Allison of The Crickets. Originally, the song was going to be named “Cindy Lou” after Holly’s niece, but Allison convinced Holly to change it to “Peggy Sue” in honor of his girlfriend (and later wife), Peggy Sue Gerron. That personal touch only adds to the song’s sincerity.
Holly’s vocal performance is mesmerizing, with his signature hiccuping delivery and smooth phrasing making each line feel urgent and heartfelt. The lyrics are simple but effective, expressing admiration and longing in a way that feels both personal and universal. “If you knew, Peggy Sue, then you’d know why I feel blue,” Holly sings, capturing the ache of young love.
“Peggy Sue” became a massive hit, reaching No. 3 on the Billboard charts. Over the years, it has remained one of Holly’s most beloved tracks, covered by countless artists, including John Lennon. Its unique combination of rhythm, melody, and emotional depth ensures that it will never fade from rock and roll history.
3. “Everyday” (1957)
“Everyday” is a rare gem in Buddy Holly’s catalog—a song that feels as fresh and heartfelt today as it did in 1957. With its simple yet profoundly uplifting lyrics, this track captures the excitement and anticipation of young love. Unlike some of Holly’s more rhythm-driven rock and roll hits, “Everyday” is a delicate, almost lullaby-like tune that showcases his softer side.
One of the most striking elements of “Everyday” is its instrumentation. Instead of a traditional drumbeat, producer Norman Petty’s wife, Vi Petty, plays a celesta, a bell-like keyboard instrument that gives the song its magical, dreamy quality. Meanwhile, Jerry Allison provides percussion by rhythmically slapping his knees, adding to the song’s light, intimate feel. This unconventional approach helped “Everyday” stand out from other rock and roll songs of its time.
Holly’s lyrics are hopeful and sincere: “Every day, it’s a-gettin’ closer, goin’ faster than a roller coaster.” The song beautifully captures the anticipation of love growing stronger, and Holly’s warm vocal delivery makes the sentiment feel genuine.
Though it was originally released as the B-side to “Peggy Sue,” “Everyday” has become one of Holly’s most enduring songs, covered by artists like James Taylor and Fiona Apple. Its simplicity, charm, and emotional honesty have ensured that it remains a timeless classic, proving that sometimes, less is truly more.
4. “Oh Boy!” (1957)
If there’s one Buddy Holly song that radiates pure excitement, it’s “Oh Boy!” Released in 1957, this track is a high-energy declaration of love, brimming with youthful enthusiasm and rock and roll swagger. With its electrifying rhythm and infectious melody, “Oh Boy!” became an instant favorite among fans and remains a staple of early rock history.
The song wastes no time in grabbing attention, launching into an energetic guitar riff before Holly’s voice bursts in with uncontainable joy. “All of my love, all of my kissin’, you don’t know what you’ve been missin’!” The lyrics are straightforward but effective, capturing the thrill of new romance with an almost breathless excitement.
Musically, “Oh Boy!” is a perfect example of Holly’s ability to blend rockabilly energy with pop sensibility. His signature hiccuping vocal style adds an extra layer of charisma, while the backing harmonies from The Crickets reinforce the song’s upbeat, celebratory feel. The track’s driving beat and rhythmic strumming make it impossible to sit still while listening.
Upon its release, “Oh Boy!” quickly climbed the charts, solidifying Holly’s status as a rock and roll star. It has since been covered by numerous artists, including The Everly Brothers and Bruce Springsteen, a testament to its lasting influence. To this day, “Oh Boy!” remains one of Buddy Holly’s most beloved songs, an irresistible anthem of love and excitement that never loses its spark.
5. “Rave On” (1958)
“Rave On” is one of Buddy Holly’s most electrifying songs—a fast-paced, adrenaline-fueled rock and roll anthem that perfectly captures the rebellious spirit of the 1950s. Released in 1958, this track is a short but explosive burst of energy, showcasing Holly’s signature hiccuping vocals and undeniable charisma.
Unlike many of Holly’s self-penned hits, “Rave On” was written by Sonny West, Bill Tilghman, and Norman Petty. However, once Holly put his spin on it, the song became unmistakably his. The title itself is a call to celebrate rock and roll, urging listeners to let loose and embrace the joy of music. From the moment the song starts, Holly’s energetic vocal delivery commands attention, and his infectious enthusiasm is impossible to resist.
Clocking in at just over two minutes, “Rave On” wastes no time in getting to the point. The rapid-fire lyrics and upbeat melody make it a dancefloor favorite, while the song’s message—about the power of love and music—is universal. “Rave on, it’s a crazy feeling, and I know it’s got me reeling!” Holly exclaims, perfectly capturing the intoxicating rush of both romance and rock and roll.
Though it wasn’t his biggest chart hit, “Rave On” became one of Holly’s most celebrated songs, covered by legends like Bruce Springsteen and John Mellencamp. Its influence can still be heard in rock music today, proving that Buddy Holly’s spirit will continue to “rave on” for generations to come.
6. “Not Fade Away” (1957)
Few songs in rock and roll history have had as much of a lasting impact as “Not Fade Away.” Released in 1957, this track is a prime example of Buddy Holly’s innovative approach to rhythm and melody. With its infectious Bo Diddley-inspired beat, “Not Fade Away” became a blueprint for countless rock bands that followed, including The Rolling Stones, who famously covered it in 1964.
At its core, “Not Fade Away” is a declaration of unwavering love and devotion. “I’m a-gonna tell you how it’s gonna be, you’re gonna give your love to me.” Holly’s confident delivery makes it clear that this is more than just a love song—it’s a bold, rhythmic statement. The song’s driving beat, created through handclaps and percussion, gives it an irresistible groove that compels listeners to move.
Unlike many of his other hits, “Not Fade Away” relies more on its rhythm than melody, showing Holly’s ability to push the boundaries of rock and roll. His hiccuping vocal style adds personality and charm, making the song instantly recognizable.
Despite not being a massive hit upon release, “Not Fade Away” has grown in stature over the years, with its influence echoing through rock music for decades. The song’s raw energy and timeless appeal make it one of Buddy Holly’s most enduring classics, proving that his music truly will “not fade away.”
7. “Maybe Baby” (1958)
With its irresistible melody and heartfelt lyrics, “Maybe Baby” is one of Buddy Holly’s most charming love songs. Released in 1958, the track showcases his knack for crafting catchy, radio-friendly tunes while maintaining the sincerity and authenticity that made him a rock and roll icon.
“Maybe Baby” tells the story of hopeful, unrequited love, with Holly expressing the uncertainty and excitement of waiting for romance to blossom. “Maybe baby, I’ll have you, maybe baby, you’ll be true.” The lyrics are simple yet deeply relatable, capturing the universal feeling of longing for someone special.
Musically, the song features a polished blend of rockabilly and pop, driven by a smooth, upbeat rhythm. Holly’s vocals are playful yet earnest, conveying both optimism and vulnerability. The backing harmonies from The Crickets add to the song’s warmth, creating a sound that feels both intimate and full of life.
“Maybe Baby” became one of Holly’s most beloved songs, continuing to be covered by artists across multiple genres. It remains a testament to his ability to craft songs that resonate with listeners of all ages. Whether you’re experiencing love for the first time or reminiscing about youthful romance, “Maybe Baby” captures that magic effortlessly.
8. “It’s So Easy” (1958)
“It’s So Easy” is one of Buddy Holly’s most effortlessly cool tracks. Released in 1958, this song perfectly embodies the smooth confidence and charm that defined much of his music. Though it wasn’t a massive hit during his lifetime, “It’s So Easy” has since become a beloved classic, thanks in part to its catchy melody and laid-back groove.
The song’s lyrics are playful and carefree, celebrating how simple love can be when it feels right. “It’s so easy to fall in love.” Holly delivers these words with a natural charisma, making the song feel both romantic and fun. His vocal performance is relaxed yet engaging, drawing listeners in with every note.
Musically, “It’s So Easy” stands out for its light, bouncy rhythm and crisp guitar work. Unlike some of his more intense rock and roll hits, this track has a breezy quality that makes it perfect for singing along. The Crickets’ harmonies provide the perfect backdrop, enhancing the song’s effortless charm.
Over the years, “It’s So Easy” has been covered by numerous artists, most notably Linda Ronstadt, whose 1977 version brought the song back into the spotlight. Today, it remains one of Holly’s most enduring tracks, proving that great music truly is timeless—and that falling in love really can be “so easy.”
9. “Heartbeat” (1958)
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“Heartbeat” is a song that perfectly captures the excitement and nervousness of young love. Released in 1958, it showcases Buddy Holly’s ability to blend heartfelt emotion with a catchy, danceable rhythm. While not one of his biggest hits at the time, “Heartbeat” has since become a fan favorite, with its simple yet powerful melody standing the test of time.
The lyrics of “Heartbeat” are straightforward yet deeply relatable. Holly expresses the thrill of being in love, comparing it to the steady beat of his heart. “Heartbeat, why do you miss when my baby kisses me?” This line encapsulates the nervous energy and anticipation that comes with being smitten by someone special.
Musically, the song has a light, almost hypnotic quality. The rhythm is steady and infectious, driven by a simple drumbeat and a clean guitar line. Holly’s vocals are smooth and warm, perfectly conveying the sincerity of the lyrics. The backing vocals from The Crickets add an extra layer of charm, making the song feel even more intimate.
Though it didn’t achieve massive commercial success initially, “Heartbeat” has gained recognition over the years, covered by artists like The Dave Clark Five and Elvis Costello. Today, it remains one of Buddy Holly’s most tender and enduring songs, reminding us all of the excitement and uncertainty of falling in love.
10. “Words of Love” (1957)
“Words of Love” is one of Buddy Holly’s most beautifully crafted songs, showcasing his softer, more romantic side. Released in 1957, this track was notable for its innovative use of overdubbing, allowing Holly to harmonize with himself and create a lush, layered sound that was ahead of its time.
Unlike his more energetic rock and roll hits, “Words of Love” is a gentle, almost meditative ballad. The lyrics are simple but poignant, expressing the timeless theme of love through tender and reassuring words. “Words of love you whisper soft and true, darling, I love you.” Holly’s delivery is heartfelt, making the song feel deeply personal.
The instrumentation is minimal but effective, with a delicate guitar melody and subtle percussion creating a dreamy atmosphere. This stripped-down approach allows Holly’s vocals to take center stage, highlighting the emotion in his performance. The song’s harmonic structure was unique for its time, influencing later artists like The Beatles, who recorded their own version in 1964.
Though “Words of Love” wasn’t a major hit when it was first released, it has since become one of Holly’s most cherished recordings. Its timeless melody and heartfelt lyrics make it a standout in his catalog, proving that true love—and great music—never go out of style.
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.
