In the realm of rock and roll, few names resonate as profoundly as Buddy Holly. A pioneer whose innovative sound and heartfelt lyrics helped shape the future of music, Holly’s influence can still be felt today. Emerging in the late 1950s, he crafted a unique blend of rock, pop, and country that captivated audiences and inspired countless artists. Tragically, his life was cut short at just 22, but his legacy endures through a remarkable catalog of songs that still play on radio stations and playlists worldwide.
From infectious melodies to poignant ballads, Holly’s music captures the essence of youthful exuberance and the bittersweet nature of love. His pioneering use of studio techniques and his distinctive voice set him apart from his contemporaries, making him a lasting icon in the music industry. In this article, we explore the top 10 most popular Buddy Holly songs of all time, showcasing the tracks that not only defined his career but also left an indelible mark on the fabric of rock music. Join us as we celebrate the timeless brilliance of Buddy Holly and discover why his songs continue to resonate with fans old and new.
1. “Peggy Sue” (1957)
“Peggy Sue” is one of those rare songs that instantly grabs your ear and never really lets go. Released in 1957, it was a groundbreaking hit that captured the spirit of the era with a mix of youthful energy, musical innovation, and just the right touch of longing. Buddy Holly’s hiccup-like vocal delivery—playful, urgent, and completely distinctive—adds a charming vulnerability to the song. He’s not just singing about Peggy Sue; he’s aching for her, pleading with her, celebrating her in that repetitive, hypnotic chorus. The iconic drum pattern, played by Jerry Allison, helped shape the rhythmic foundation of early rock and roll. There’s a rawness to the track, but also a perfect polish: the kind of effortless cool that defined Buddy Holly’s style. What makes “Peggy Sue” so timeless is its simplicity wrapped in sophistication. It’s a love song, yes, but it also feels like an anthem for every teenager who’s ever felt their heart race at the sound of a name. Decades later, “Peggy Sue” still pulses with life, influencing everyone from The Beatles to modern indie bands. It’s a reminder of just how fresh and radical Buddy Holly’s sound was—and how it still sounds just right.
2. “That’ll Be the Day” (1957)
“That’ll Be the Day” is the moment where Buddy Holly went from rising star to full-blown rock and roll legend. Released in 1957, the song captures the perfect mix of swagger and sadness, combining catchy hooks with a deeply human sense of frustration and doubt. Inspired by a line from a John Wayne movie, the phrase “that’ll be the day” becomes both a challenge and a resignation—a bold face hiding heartbreak. Holly’s voice is both playful and biting, and his signature twang on the guitar glides through the melody like a confident strut. The rhythm has a rolling, laid-back charm that gives the song a timeless appeal. It’s the kind of track that makes you tap your foot without even realizing it. More than just a hit single, “That’ll Be the Day” signaled a new kind of rock and roll: clever, emotionally layered, and built around a voice that didn’t need to shout to be heard. It reached No. 1 on the charts and paved the way for countless artists who followed. To this day, the song feels alive—sharp, cool, and full of that sly romantic defiance that never goes out of style.
3. “Everyday” (1957)
“Everyday” is a gentle masterpiece—a short, sweet tune that says more in two minutes than many songs say in five. Released in 1957, this Buddy Holly classic strips away all excess to reveal something honest, tender, and quietly magical. With its soft celesta melody (played by producer Norman Petty’s wife) and the subtle clap-like percussion, “Everyday” feels like it was recorded in a dream. Holly’s vocals are warm and boyish, full of affection but never forced. He sings about the slow, growing excitement of falling in love—how each passing moment brings two people closer. There’s an innocence here that’s rare in rock and roll, but it never feels naïve. Instead, it feels like a love letter whispered just loud enough for the world to hear. The song’s restraint is its power. It doesn’t need to be loud to make you feel something deep. “Everyday” has been covered and referenced by artists across genres—from country to pop to indie rock—and its message of quiet joy has never lost its relevance. It’s one of those rare songs that feels both timeless and personal, like it was written just for you.
4. “Oh, Boy!” (1957)
“Oh, Boy!” bursts out of the speakers with all the excitement of a first crush. Released in 1957, this track is Buddy Holly at his most exuberant—an explosion of teen energy, romance, and rock and roll fun. Backed by the Crickets, Holly rides a wave of jangling guitars and handclaps as he sings about the thrill of being in love. The lyrics don’t overthink things: they’re pure joy, all heart and hormones. “All my love, all my kissin’, you don’t know what you’ve been missin’”—he’s not just singing it, he’s grinning it. The harmonies soar, the tempo never lets up, and everything about the song feels designed to make you dance, smile, and fall in love a little bit yourself. What makes “Oh, Boy!” so special is how unpretentious it is. It doesn’t try to be poetic or profound. It just wants you to feel good—and it succeeds completely. This song helped solidify Holly’s status as a rock and roll icon and gave generations of fans a reason to shout those two little words with unfiltered glee. More than sixty years later, it still feels like falling in love for the first time.
5. “Not Fade Away” (1957)
“Not Fade Away” is one of Buddy Holly’s most rhythmically bold and forward-thinking tracks. Released in 1957, this song pulses with confidence and raw charm, propelled by a distinctive Bo Diddley-inspired beat that would go on to influence a generation of rock musicians. From the first clap-and-thump rhythm, it’s clear this is no ordinary love song. Holly’s voice swaggers across the track, proclaiming a kind of defiant devotion: he’s not just in love—he’s in it forever. “My love’s bigger than a Cadillac,” he boasts, with a grin in his tone. The lyrics are simple but full of impact, and the stripped-down instrumentation leaves room for the beat to do the talking. It’s no surprise that this song has been covered by everyone from The Rolling Stones to Rush—it taps into something primal and universal. “Not Fade Away” doesn’t just promise enduring love—it proves that the spirit of rock and roll itself doesn’t fade. Buddy Holly was only in his early twenties when he recorded it, but he already understood how to make music that lasts. Decades later, that heartbeat rhythm and Holly’s earnest promise still feel just as alive and urgent.
6. “Rave On” (1958)
“Rave On,” released in 1958, is Buddy Holly in full rock and roll glory—loud, lively, and utterly contagious. From the moment the song kicks off, it races forward with a joyful urgency that perfectly captures the wide-eyed excitement of young love. Holly’s vocal delivery is wild and exuberant, full of hiccups, yelps, and that unmistakable Texan twang. There’s a sense that he’s barely holding the melody together, and that rawness is what makes it magic. The lyrics are pure celebration: love so intense it can only be shouted. “Rave on, it’s a crazy feeling—and I know it’s got me reeling.” You can’t help but move when you hear it. The guitars jangle with manic energy, the beat jumps with a life of its own, and everything about the track says: let go and have fun. “Rave On” might not be as sentimental or polished as some of Holly’s other work, but that’s its genius. It captures the reckless thrill of being young, in love, and too full of energy to sit still. This track helped set the tone for the rock scene to come, proving that music could be both rebellious and completely joyful.
7. “True Love Ways” (1958)
“True Love Ways,” released posthumously in 1958, is one of Buddy Holly’s most tender and heartfelt recordings—a gentle ballad that reveals a side of him often overshadowed by his upbeat hits. Written as a tribute to his wife, María Elena, this song is deeply personal, and you can hear it in every note. The orchestral arrangement is lush and sweeping, a dramatic departure from his usual guitar-driven style. Holly’s voice is soft, clear, and full of warmth. There’s no bravado here—just love, laid bare. “Just you know why / Why you and I / Will by and by / Know true love ways…” The lyrics are simple but deeply poetic, conveying a timeless truth about the quiet strength of devotion. It’s the kind of song that plays at weddings, anniversaries, and moments of reflection—anywhere people want to feel something real. In many ways, “True Love Ways” feels like a goodbye letter, full of peace and tenderness. It showed that Buddy Holly was not only a rock and roll pioneer but a romantic soul with a gift for expressing love with honesty and grace. The song still moves listeners decades later, its sincerity echoing through time.
8. “It Doesn’t Matter Anymore” (1959)
Released in 1959 shortly before his tragic death, “It Doesn’t Matter Anymore” is both heartbreakingly prophetic and musically timeless. Written by Paul Anka specifically for Buddy Holly, the song captures a complex emotional blend of sorrow, release, and resilience. Unlike many breakup songs that dwell in sadness, Holly sings this one with a clear sense of letting go. His voice is steady and calm, even as he confesses deep emotional wounds. “You go your way and I’ll go mine,” he declares with a sense of quiet finality. The arrangement is elegant and sweeping, with strings that add an emotional depth beyond Holly’s earlier, rawer recordings. There’s a noticeable maturity in both the songwriting and performance—this is a man confronting life’s disappointments with grace, not bitterness. It’s hard not to listen to this track without thinking about the what-ifs of Buddy Holly’s career, which was cut far too short. Still, “It Doesn’t Matter Anymore” serves as a poignant reminder of his incredible versatility. It’s a song that resonates with anyone who’s ever had to move on, proving that strength and sadness can coexist—and that true artistry never fades.
9. “Words of Love” (1957)
“Words of Love,” released in 1957, is one of Buddy Holly’s most quietly revolutionary songs. On the surface, it’s a gentle love tune with sweet lyrics and a dreamy tempo. But behind its simplicity lies a track that helped lay the groundwork for modern pop and rock harmonies. Holly overdubbed his own voice to create layered vocals—an innovative studio trick at the time that predated and inspired groups like The Beatles, who later covered the song. The melody glides with an easy grace, and Holly’s voice is soft and affectionate, almost whispered. “Don’t you know I love you / Tell me, darling, do you?” There’s a vulnerable honesty in the delivery, like a personal confession rather than a performance. The song doesn’t demand your attention—it gently draws you in. While it may not have had the explosive popularity of his bigger hits, “Words of Love” remains a fan favorite for its purity and charm. It’s a beautiful reminder of Holly’s musical intelligence and emotional sensitivity. Even in a two-minute ballad, he knew how to make every word count, and “Words of Love” continues to be a quiet gem in the heart of his discography.
10. “Heartbeat” (1958)
“Heartbeat,” released in 1958, is a bright, rhythmic burst of pop-rock charm that captures the innocent rush of falling head-over-heels in love. Buddy Holly’s voice skips along with a lightness that perfectly matches the song’s theme—how love speeds up your heartbeat, makes time blur, and fills you with jittery excitement. The guitar has a bouncing, almost calypso-like rhythm, while the background vocals add a playful layer to the sound. “Heartbeat—why do you miss / When my baby kisses me?” he asks, a question full of sweet frustration and adolescent wonder. What makes “Heartbeat” shine is its blend of musical tightness and emotional looseness. It’s both polished and spontaneous, like a giggling confession blurted out in a moment of joy. While not as widely known as some of his bigger hits, this song captures the Buddy Holly magic: simple lyrics, an unforgettable melody, and a feeling that sticks with you long after the music stops. “Heartbeat” proves that even the smallest moments of love—the flutters, the blushes, the thrills—are worth singing about. In Holly’s hands, even a missed heartbeat becomes a celebration of being alive and in love.
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.
