Buddy Holly, a pioneering figure in rock ‘n’ roll, left an indelible mark on music history with his innovative sound and timeless melodies. Despite his brief career, which tragically ended in a plane crash at just 22, Holly’s influence continues to resonate across generations. His unique blend of rock, pop, and country elements, combined with his signature glasses and charismatic persona, made him a beloved icon.
In this article, we celebrate the top 10 most popular Buddy Holly songs of all time, exploring the tracks that not only defined an era but also shaped the future of music. From the infectious energy of “Peggy Sue” to the poignant lyrics of “True Love Ways,” each song showcases Holly’s exceptional talent as a songwriter and performer. His ability to craft relatable narratives and catchy hooks paved the way for countless artists who followed.
Join us as we take a nostalgic journey through Holly’s greatest hits, uncovering the stories behind the songs and their lasting impact. Whether you’re a lifelong fan or new to his music, this countdown promises to illuminate the genius of Buddy Holly and remind us why his legacy endures. Get ready to rock and roll!
1. “Peggy Sue” (1957)
“Peggy Sue” is one of Buddy Holly’s most iconic and enduring hits, released in 1957. Originally written as a playful tribute to drummer Jerry Allison’s girlfriend (and later wife), the song became an anthem for teenage love and 1950s youth culture. Its instantly recognizable opening guitar riff and rapid-fire drumming set the tone for an upbeat, infectious tune that grabs you from the very start. Holly’s signature hiccup-like vocal style adds a unique charm that made the track stand out. The simplicity of the lyrics—repeating the name “Peggy Sue” over a driving rhythm—feels both innocent and endlessly catchy. There’s a sense of joy and lightheartedness that perfectly captures the carefree spirit of young romance. More than just a love song, “Peggy Sue” became a symbol of rock and roll’s early days, influencing countless musicians who followed. Whether played at sock hops in the ’50s or heard on playlists today, the song’s timeless appeal continues to resonate with listeners across generations. Its energy, melody, and Holly’s charismatic delivery have secured “Peggy Sue” as one of the cornerstones of rock music history.
2. “That’ll Be the Day” (1957)
Released in 1957, “That’ll Be the Day” is the song that launched Buddy Holly into superstardom and became a defining track of the rock and roll era. Inspired by a phrase from the John Wayne film The Searchers, the title itself carries a playful sense of defiance. Musically, the track blends elements of rockabilly, country, and early rock, highlighted by a steady backbeat, jangly guitars, and Holly’s distinctive hiccup-styled vocals. Lyrically, it’s a bittersweet message about skepticism in love—declaring that certain things will only happen “that’ll be the day” when heartbreak strikes. The song’s blend of humor, melancholy, and catchy melody creates an irresistible hook that resonated deeply with audiences. It wasn’t just a hit; it became a cultural milestone that set the tone for what rock music could be—fun, emotionally honest, and rhythmically captivating. The Crickets’ tight harmonies and infectious energy complemented Holly perfectly. This track didn’t just mark the start of his career; it became one of rock’s most important building blocks, influencing generations of musicians from The Beatles to modern indie bands.
3. “Everyday” (1957)
“Everyday,” released in 1957, is one of Buddy Holly’s most charming and whimsical songs, capturing the simple joys of falling in love. What sets this track apart is its minimalistic yet innovative instrumentation—the soft tapping you hear is actually drummer Jerry Allison slapping his knees, while the glockenspiel adds a bell-like, magical quality. The song’s gentle melody is paired with lyrics that speak to the sweet anticipation of love growing stronger day by day. Holly’s tender vocal delivery feels personal, almost like he’s serenading the listener directly. There’s a purity and innocence to the song that perfectly reflects the optimism of young romance. Despite being softer and less rock-driven than some of his other hits, “Everyday” showcases Holly’s versatility as an artist who wasn’t afraid to step outside of the typical rock and roll formula. Its enduring popularity has led to countless covers and appearances in films, commercials, and TV shows. The timeless message—that good things are coming “every day”—continues to resonate, making it one of the most beloved songs in his catalog.
4. “Oh, Boy!” (1957)
Released in 1957, “Oh, Boy!” is a high-octane celebration of love, energy, and the unstoppable spirit of rock and roll. From the first strum of the guitar, the track bursts with excitement, driven by Holly’s exuberant vocals and the lively backing harmonies of The Crickets. The lyrics express the uncontainable joy of being in love, with Holly proclaiming that his feelings are so strong they can’t be denied. The rapid-fire beat and catchy melody make it practically impossible to sit still while listening—this is a song built for dancing, clapping, and singing along. “Oh, Boy!” embodies everything that made Holly a pioneer: straightforward yet deeply engaging songwriting, a contagious sense of fun, and a natural ability to connect with listeners. Its infectious rhythm and upbeat vibe made it an instant hit in the 1950s, but its appeal hasn’t faded. The song remains a staple in classic rock playlists and continues to inspire new generations of musicians who admire Holly’s ability to turn simple expressions of love into unforgettable rock and roll anthems.
5. “Rave On” (1958)
“Rave On,” released in 1958, is a thrilling burst of energy that perfectly showcases Buddy Holly’s electrifying influence on rock and roll. Right from the opening shout of “Well, the little things you say and do,” the song leaps into action with an infectious rhythm that refuses to let go. The guitar riff is raw and punchy, driving the song forward while Holly’s joyful, slightly raspy vocals express the giddy excitement of being head-over-heels in love. “Rave On” isn’t just about romance—it’s a full-on celebration of life, youth, and the power of music to make you feel alive. The title itself conveys the idea of letting loose, having fun, and embracing the moment. Unlike some of Holly’s softer tracks, this one is unapologetically bold and designed to get listeners moving. Its fast tempo and catchy hooks influenced countless rock musicians, from The Rolling Stones to Bruce Springsteen. Despite its brevity—clocking in at under two minutes—the song packs a punch that feels timeless. “Rave On” is a perfect example of Holly’s ability to blend simplicity with explosive, joyful energy.
6. “True Love Ways” (1958)
“True Love Ways,” recorded in 1958 and released posthumously, is a tender ballad that reveals Buddy Holly’s softer, more romantic side. Written as a dedication to his wife, Maria Elena, the song carries a sincerity that’s both touching and timeless. The lush orchestral arrangement, complete with sweeping strings and gentle piano, stands in contrast to Holly’s usual rock and roll sound. His smooth, heartfelt vocals convey a depth of emotion that resonates deeply, making it clear this was a very personal piece. Lyrically, the song expresses a quiet yet profound devotion, with lines that speak of enduring love and the beauty of shared moments. “True Love Ways” not only highlights Holly’s versatility as a musician but also demonstrates his growth as a songwriter, willing to experiment with different styles while staying true to his emotional core. Over the years, it has become a popular choice for weddings and romantic occasions, symbolizing the timeless nature of true love. This beautiful, moving track remains one of Holly’s most cherished and enduring contributions to music.
7. “Not Fade Away” (1957)
“Not Fade Away,” released in 1957, is a rock and roll classic that combines Buddy Holly’s signature rockabilly style with an irresistible Bo Diddley-inspired rhythm. Right from the hand-clapping intro and the steady, infectious beat, the song pulses with life and attitude. Lyrically, it’s a confident declaration of love, with Holly insisting that his feelings are strong and enduring—that they will, indeed, not fade away. His vocal delivery is full of swagger, complemented by the raw, chugging guitar riff that gives the track its driving momentum. This song marked a significant step forward in the blending of blues, rock, and pop influences, paving the way for future generations of rock musicians. The Rolling Stones famously covered it, turning it into one of their earliest hits, further cementing its place in rock history. “Not Fade Away” perfectly captures the defiant spirit of young love and the enduring power of music. It remains a testament to Holly’s ability to craft simple yet incredibly impactful songs that continue to resonate decades after their release.
8. “Words of Love” (1957)
Released in 1957, “Words of Love” is one of Buddy Holly’s most tender and innovative songs, offering a gentle, romantic message wrapped in beautiful harmonies. Unlike many of his more energetic rock tunes, this track takes a softer approach, focusing on the power of spoken affection in relationships. Holly’s layered vocals—achieved through overdubbing, a relatively new recording technique at the time—create a warm, echoing effect that feels intimate and heartfelt. The lyrics are simple but profound, urging that “words of love, softly spoken” are the key to nurturing and sustaining romance. Musically, the track features delicate guitar picking and a steady rhythm that perfectly complements the mood. “Words of Love” not only showcased Holly’s ability to write meaningful, melodic ballads but also highlighted his pioneering use of recording technology that would later influence bands like The Beatles, who covered this song in tribute. It’s a timeless reminder of how even the simplest expressions of love, when delivered sincerely, can leave a lasting impact.
9. “It Doesn’t Matter Anymore” (1959)
“It Doesn’t Matter Anymore,” released in 1959 shortly after Buddy Holly’s tragic death, carries a poignant weight as one of his final recordings. Written by Paul Anka specifically for Holly, the song blends elements of pop and orchestral arrangement with Holly’s smooth, heartfelt vocal delivery. The lyrics convey a sense of resignation after heartbreak—acknowledging that things have gone wrong but choosing to let go and move forward. There’s a bittersweet tone to the track; while the melody is bright and somewhat upbeat, the words reflect sadness and acceptance. The lush string arrangement was a departure from Holly’s usual rockabilly sound, signaling the artistic growth and experimentation he was embracing before his untimely passing. The song became a hit not just because of its musical quality, but because it felt like a farewell, both from Holly to the world and from the world to Holly. Over the decades, “It Doesn’t Matter Anymore” has continued to resonate with listeners as a song of closure, strength, and bittersweet beauty.
10. “Listen to Me” (1958)
“Listen to Me,” released in 1958, is a beautifully introspective track that showcases Buddy Holly’s gentler, more contemplative side. Unlike the energetic rock anthems that made him famous, this song trades electric guitars for a softer acoustic-driven arrangement, allowing Holly’s voice to take center stage. The lyrics are an earnest plea for attention and understanding in a relationship, capturing the vulnerability that comes with truly opening one’s heart to another. His vocals are tender yet powerful, full of sincerity that makes the listener feel as though Holly is speaking directly to them. The melody is simple but hauntingly beautiful, supported by subtle guitar work and understated percussion. “Listen to Me” is a testament to Holly’s versatility—not just as a rock pioneer, but as a songwriter capable of conveying deep emotional truths. It stands as one of the quieter gems in his discography, offering a more intimate glimpse into the man behind the music. The song’s heartfelt message remains timeless, continuing to touch the hearts of listeners more than six decades later.
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.
