Buddy Holly, a pioneer of rock and roll, left an indelible mark on the music industry despite his tragically short career. With his signature glasses, infectious energy, and unparalleled ability to craft timeless melodies, Holly became a trailblazer who inspired generations of musicians—from The Beatles to modern-day rock legends. His unique blend of rockabilly, rhythm and blues, and heartfelt lyricism catapulted him to stardom in the 1950s, and his influence continues to echo through the halls of music history.
In this article, we’re diving into the top 10 most popular Buddy Holly songs of all time, celebrating the hits that made him a household name and secured his place as one of the greatest songwriters to ever grace the stage. From toe-tapping rock anthems to tender ballads that tug at your heartstrings, these songs represent the very best of Buddy Holly’s genius. Whether you’re a lifelong fan or just discovering his music for the first time, this list will take you on a journey through the golden age of rock and roll. So, grab your record player—or your favorite streaming app—and get ready to relive the magic of Buddy Holly’s unforgettable hits!
1. That’ll Be the Day (1957)
Buddy Holly’s “That’ll Be the Day” is one of the most defining songs of the early rock and roll era. Released in 1957, it was the track that launched Buddy Holly and the Crickets into stardom, setting the stage for a career that would influence countless musicians. The title comes from a phrase John Wayne repeatedly says in the 1956 Western The Searchers, and that casual confidence is reflected in the song’s lyrics and delivery.
Built around a bluesy chord progression, the song’s infectious melody and Holly’s distinctive hiccup-style vocals give it an undeniable charm. The Crickets’ tight instrumentation, especially the driving rhythm guitar and steady drumbeat, add to the song’s irresistible energy. Though the lyrics tell the story of a heartbroken lover feigning indifference, there’s a playful defiance in Holly’s voice that makes the song feel more like an anthem of resilience than sorrow.
“That’ll Be the Day” quickly became a massive hit, topping the Billboard charts and cementing Buddy Holly’s place in rock history. Its influence stretches far beyond the 1950s—The Beatles famously recorded it as their first demo, and it remains one of the most celebrated songs of the rock and roll revolution.
2. Peggy Sue (1957)
Few songs capture the essence of teenage romance as perfectly as “Peggy Sue.” Released in 1957, this rock and roll classic showcases Buddy Holly’s innovative guitar playing and signature vocal style, complete with his famous hiccups and rhythmic phrasing. Originally titled “Cindy Lou,” the song was renamed in honor of Peggy Sue Gerron, the girlfriend (and later wife) of Crickets drummer Jerry Allison.
One of the song’s most striking elements is its rolling drumbeat, which gives it a hypnotic, pulsing energy. Unlike many rock hits of the time, “Peggy Sue” doesn’t rely on a traditional backbeat; instead, Allison’s drumming is front and center, creating a sense of urgency and excitement. Holly’s dynamic guitar work complements the beat perfectly, adding to the song’s sense of movement and joy.
Lyrically, “Peggy Sue” is a simple love song, but Holly’s passionate delivery elevates it into something special. His longing and admiration come through in every line, making it easy for listeners to connect with the sentiment. The song became a huge hit, reaching the Top 10 on the charts, and it remains one of Buddy Holly’s most enduring and beloved recordings.
3. Everyday (1957)
“Everyday” is a beautifully understated love song that showcases Buddy Holly’s softer, more introspective side. Released in 1957 as the B-side to “Peggy Sue,” the track has since become one of his most cherished recordings, thanks to its gentle optimism and heartfelt simplicity.
What makes “Everyday” stand out is its unique instrumentation. Instead of a traditional drumbeat, the rhythm comes from producer Norman Petty’s wife, Vi, tapping on her knees. This light, percussive sound is paired with a celesta—a delicate, bell-like keyboard instrument—that gives the song an almost dreamlike quality. Holly’s vocals are warm and sincere, perfectly matching the song’s hopeful message about love growing stronger over time.
Lyrically, the song captures the excitement of a relationship unfolding, with lines like “Every day, it’s a-gettin’ closer, goin’ faster than a rollercoaster” evoking the thrill of falling in love. There’s an innocence to the track that makes it feel timeless, and its minimalistic approach highlights Holly’s ability to convey deep emotion without excess.
“Everyday” may not have been a chart-topping hit at the time, but its influence has only grown over the decades. It has been featured in countless movies, TV shows, and commercials, solidifying its place as one of the most endearing love songs in rock and roll history.
4. Rave On (1958)
“Rave On” is an electrifying burst of rock and roll energy that perfectly captures the excitement of Buddy Holly’s music. Released in 1958, the song was originally written by Sonny West, Bill Tilghman, and Norman Petty, but it was Holly’s version that transformed it into a rock classic. Clocking in at just over a minute and a half, the track wastes no time in delivering its high-energy punch.
From the very first note, “Rave On” is pure adrenaline. The opening drumbeat and chugging guitar immediately set a fast-paced groove, and Holly’s enthusiastic vocals bring the lyrics to life. The song’s message is simple but infectious—an ode to the power of music and the joy it brings. Holly’s signature hiccuping vocal style adds to the excitement, making it impossible to sit still while listening.
Though short in length, “Rave On” leaves a lasting impact. Its high-energy sound was ahead of its time, influencing many future rock artists. The song remains a staple of Holly’s discography, proving that great rock and roll doesn’t have to be complicated—it just needs passion, rhythm, and an irresistible melody.
5. Oh Boy! (1957)
“Oh Boy!” is one of Buddy Holly’s most exuberant and joyful recordings, released in 1957 as a single alongside his band, The Crickets. Written by Sonny West, Bill Tilghman, and Norman Petty, the song became an instant hit thanks to its upbeat tempo, catchy melody, and Holly’s charismatic performance.
The song radiates excitement from the very beginning, with an energetic guitar riff and driving rhythm that set the stage for Holly’s enthusiastic vocals. The lyrics celebrate the thrill of being in love, with lines like “All of my love, all of my kissin’, you don’t know what you’ve been missin’” delivering a message of pure, youthful passion. Holly’s vocal delivery is filled with excitement, making it easy to believe that he truly means every word.
“Oh Boy!” quickly became a fan favorite and one of Holly’s signature songs. It was a staple of his live performances and continues to be one of the most recognizable tracks from the golden era of rock and roll. The song’s infectious energy has kept it relevant for decades, proving that Buddy Holly’s music still has the power to make people smile and dance.
6. It’s So Easy (1958)
“It’s So Easy” is a perfect example of Buddy Holly’s ability to craft simple yet irresistible rock and roll tunes. Released in 1958, the song has a breezy, carefree vibe that makes it instantly likable. Though it wasn’t a major hit upon its initial release, it has since become a beloved part of Holly’s catalog, with later artists, including Linda Ronstadt, recording their own successful versions.
Musically, “It’s So Easy” stands out for its smooth, rolling rhythm and Holly’s relaxed yet playful vocal delivery. The song’s structure is straightforward, but that’s part of its charm—it’s effortlessly catchy, the kind of song you find yourself singing along to after just one listen. The lyrics capture the thrill of being in love, with Holly expressing how easy it is to give his heart away.
Despite its initial commercial underperformance, “It’s So Easy” has endured over the decades. It showcases Holly’s talent for blending rock and roll with pop sensibilities, and its lighthearted energy ensures it remains a favorite among fans. The song proves that sometimes, the best rock and roll is the kind that feels as effortless as love itself.
7. Not Fade Away (1957)
“Not Fade Away” is a revolutionary track that introduced a distinctive rhythm to rock and roll, heavily inspired by the legendary Bo Diddley beat. Released in 1957, this song stands out in Buddy Holly’s catalog for its infectious groove, hypnotic rhythm, and confident lyrics. Though it was only a B-side to the single “Oh Boy!,” it has since become one of Holly’s most influential recordings.
Built around a relentless, handclap-driven beat, “Not Fade Away” breaks away from traditional rock rhythms of the time. The song’s lyrics are just as memorable, with Holly declaring that his love will never waver, “gonna tell you how it’s gonna be, you’re gonna give your love to me.” His delivery is bold and self-assured, making it clear that this isn’t just another love song—it’s a declaration.
Over the years, “Not Fade Away” has been covered by countless artists, most famously The Rolling Stones, who turned it into a hit of their own in 1964. Its influence on rock and roll is undeniable, proving that Buddy Holly wasn’t just a great songwriter—he was a pioneer who helped shape the future of music.
8. Maybe Baby (1958)
“Maybe Baby” is a quintessential Buddy Holly song, blending rock and roll energy with an irresistible melody and a touch of vulnerability. Released in 1958, the song became one of Holly’s most well-known hits, capturing the uncertainty and excitement of young love.
The song opens with a smooth, rolling guitar riff that immediately sets the tone for Holly’s playful yet heartfelt vocal performance. The lyrics tell the story of a hopeful romantic, unsure if his love will ever be returned but unable to let go of the possibility. “Maybe baby, I’ll have you,” Holly sings with a mix of longing and optimism, making the song both relatable and deeply endearing.
“Maybe Baby” was a commercial success, becoming a hit in both the U.S. and the U.K. Its polished production and seamless blend of rock and pop elements made it a standout in Holly’s catalog. Even today, the song remains a favorite among fans, serving as a reminder of Buddy Holly’s incredible ability to make every lyric, melody, and guitar riff feel fresh and timeless.
9. It Doesn’t Matter Anymore (1959)
Released posthumously in 1959, “It Doesn’t Matter Anymore” is one of Buddy Holly’s most poignant recordings. Written by Paul Anka, the song marked a shift in Holly’s style, featuring lush orchestration rather than the raw rock and roll sound of his earlier hits. The result is a bittersweet breakup ballad that feels both deeply emotional and musically sophisticated.
Unlike many breakup songs filled with sorrow, “It Doesn’t Matter Anymore” carries a tone of resignation rather than despair. The lyrics tell the story of someone moving on from a failed relationship, accepting that no amount of sadness will change the past. Holly’s smooth vocals glide effortlessly over the gentle rhythm, capturing a sense of both heartache and closure.
Tragically, the song was released just weeks after Holly’s untimely death in a plane crash. It became one of his last major hits, further solidifying his legacy. Today, “It Doesn’t Matter Anymore” stands as a testament to Holly’s versatility as an artist, showing that he could master both rock and roll anthems and beautifully crafted ballads.
10. Words of Love (1957)
“Words of Love” is one of Buddy Holly’s most delicate and beautifully crafted songs, showcasing a softer side of his songwriting. Released in 1957, the track stands out for its gentle, heartfelt lyrics and its innovative use of overdubbing—a technique Holly mastered to create rich vocal harmonies. While the song didn’t achieve major chart success at the time, it has since become one of his most revered recordings and was later famously covered by The Beatles.
The song’s melody is dreamy and romantic, with Holly’s voice layered over itself to create a warm, echoing effect. This early use of multi-tracking was groundbreaking for its time, demonstrating Holly’s forward-thinking approach to recording. Lyrically, “Words of Love” is a simple yet sincere declaration of affection, urging a lover to express their feelings openly. Lines like “Hold me close and tell me how you feel, tell me love is real” encapsulate the innocence and tenderness that defined Holly’s music.
Though it wasn’t a major hit upon release, “Words of Love” gained new life when The Beatles recorded their own version in 1964, introducing the song to a new generation of listeners. Their rendition stayed true to Holly’s original vision, further cementing the song’s place in rock and roll history. Today, “Words of Love” remains one of Buddy Holly’s most cherished tracks, a timeless ballad that continues to capture hearts with its sincerity and innovation.
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.
