Few artists have left an indelible mark on music history quite like Buddy Holly. Known for his signature horn-rimmed glasses, infectious melodies, and innovative approach to rock ‘n’ roll, Holly’s influence on modern music is immeasurable. Though his career was tragically short-lived, his groundbreaking contributions continue to inspire generations of musicians and fans around the world.
From heartfelt ballads to toe-tapping rock anthems, Buddy Holly’s discography is a treasure trove of unforgettable tunes. His knack for blending raw emotion with irresistible rhythm solidified his place as one of the true pioneers of rock music. Holly’s songs didn’t just dominate the charts in the late 1950s—they laid the foundation for what rock ‘n’ roll would become, influencing legends like The Beatles, Bob Dylan, and countless others.
In this article, we’ll take a nostalgic journey through Buddy Holly’s top 10 most popular songs of all time. Whether you’re a lifelong fan or discovering his magic for the first time, these timeless hits will remind you why Buddy Holly remains a beloved icon decades after his untimely passing. So, tune your ears and get ready to rock—because Buddy Holly’s music is here to stay!
1. That’ll Be the Day (1957)
“That’ll Be the Day” is more than just a hit—it’s a defining moment in rock and roll history. Released in 1957, this song became Buddy Holly’s breakthrough and remains one of the most memorable tunes of the era. Inspired by a line John Wayne delivers in the film The Searchers, the track blends swagger with a subtle undercurrent of heartache. Holly’s vocal performance is equal parts confident and vulnerable, striking a perfect balance that resonates with anyone who’s been let down in love. The rhythmic guitar strumming, the tight harmonies, and that unmistakable hiccup in Holly’s voice all come together to create something timeless. It’s got an edge, but it’s not bitter—just real. The song’s success helped establish Holly as a pioneer of early rock, and it set the tone for countless artists who followed. Its influence can be heard across decades, from The Beatles to Bruce Springsteen. What makes “That’ll Be the Day” so enduring is its raw authenticity—it’s catchy, it’s emotional, and it still hits just as hard today as it did back in ’57. This wasn’t just a radio hit—it was a cultural shift, marking the arrival of a bold new sound in American music.
2. Peggy Sue (1957)
“Peggy Sue” is Buddy Holly at his most charming and innovative. Released in 1957, this rock and roll love song instantly captivated audiences with its catchy rhythm and hypnotic beat. From the very first drum roll—those stuttering, syncopated hits—you know you’re in for something special. The lyrics are simple and sincere, a direct serenade to a girl named Peggy Sue, and Holly’s voice trembles with emotion as he sings her name again and again, turning it into a melody all its own. But what really makes this song stand out is the production. The recording’s dynamic sound, with its clean guitar riffs and rolling toms, was ahead of its time. Interestingly, Peggy Sue wasn’t just a fictional muse—she was the girlfriend (and later, wife) of drummer Jerry Allison, and the track was originally titled “Cindy Lou” before being renamed in her honor. It’s that personal connection that gives the song its authenticity. Holly’s delivery is both youthful and heartfelt, which is why “Peggy Sue” still strikes a chord all these years later. It’s not just a love song—it’s a snapshot of 1950s teenage yearning, wrapped up in under three minutes of rock and roll perfection.
3. Everyday (1957)
“Everyday” shows a softer, more introspective side of Buddy Holly, and it’s a masterclass in minimalism. Released in 1957, this track takes a completely different approach from his more raucous hits. Instead of electric guitars and a full drum kit, we get the delicate chime of a celesta and the gentle pat of handclaps. It feels intimate—like Holly is singing right in your ear. The lyrics are sweet and hopeful, describing the feeling of love growing “a little bit stronger, every day.” There’s something almost magical about how simple the song is, yet how deeply it resonates. It’s about love, yes, but also about the passage of time and the quiet moments that make life beautiful. Holly’s vocal delivery is tender, boyish, and filled with optimism. “Everyday” became a favorite not just for its uniqueness, but for the emotional weight it carries in such a light package. It’s been covered by countless artists, featured in films, and even used in commercials—but it never loses its charm. This track proves that sometimes, less really is more. “Everyday” isn’t just a love song—it’s a gentle reminder of the joy found in life’s simplest moments.
4. Oh Boy! (1957)
When “Oh Boy!” hit the airwaves in 1957, it felt like an explosion of pure joy. Buddy Holly and the Crickets delivered a track that was full of life, love, and youthful energy. From the opening chords, it’s all go—the rhythm is driving, the harmonies are tight, and Holly’s voice brims with excitement. The lyrics are a celebration of being in love and not caring who knows it: “All my love, all my kissin’ / You don’t know what you’ve been a-missin’.” It’s catchy, upbeat, and practically demands you sing along. What sets this song apart is the sheer exuberance it radiates. There’s no holding back—this is rock and roll joy in its purest form. It’s also a great example of Holly’s chemistry with The Crickets, whose backing vocals give the track its rich, layered sound. “Oh Boy!” became an instant hit, capturing the essence of 1950s teenage enthusiasm and setting the dance floors on fire. It’s not just a fun song—it’s a reminder of a time when rock and roll was still new, thrilling, and changing everything. Even today, “Oh Boy!” feels fresh and alive, a perfect snapshot of love-fueled excitement.
5. Not Fade Away (1957)
“Not Fade Away,” released in 1957, is one of Buddy Holly’s most influential and enduring tracks—a song that refuses to be forgotten, just like its title promises. Drawing inspiration from Bo Diddley’s signature rhythm, the song introduces a heartbeat-like beat that instantly gets under your skin. With its raw energy, hand-claps, and driving guitar, the track feels almost ahead of its time. It was rock and roll stripped down to its bones, and yet, it throbbed with vitality. Lyrically, Holly delivers a powerful message of unwavering love and devotion—but he does it with a cocky, confident edge: “I’m gonna tell you how it’s gonna be / You’re gonna give your love to me.” It’s not aggressive, but it’s assertive, and that swagger helped set the tone for rock frontmen in the years to come. “Not Fade Away” became even more iconic when The Rolling Stones covered it in the 1960s, proving its timelessness and far-reaching impact. But Buddy’s original still stands tall—gritty, sincere, and packed with rhythm. The song is a bold declaration, both musically and emotionally, and it remains a testament to Holly’s groundbreaking fusion of blues, rock, and pop sensibilities.
6. Rave On (1958)
“Rave On,” released in 1958, is Buddy Holly in full-blown rock and roll mode—unapologetic, wild, and full of youthful spirit. Right from the jump, the song’s energy is electric. It barrels forward with jangling guitars, a driving beat, and Holly’s unmistakable vocal hiccups that inject the track with raw personality. It’s not just a love song—it’s a love explosion. Holly doesn’t just sing about romance—he celebrates it with uncontainable excitement. The lyrics are simple and exuberant: “Rave on for me a-cause I love you / Rave on for me a-cause I want you.” It’s almost as if the music itself is alive, pushing the boundaries of early rock and creating something thrillingly new.
What makes “Rave On” so legendary is its sense of freedom. It’s rebellious, it’s joyous, and it’s totally unfiltered. Holly’s voice leaps and cracks with intensity, showing just how much fun he’s having—and inviting listeners to do the same. It’s one of those tracks that makes you want to move, dance, or shout along with the chorus. And though it’s just over two minutes long, “Rave On” manages to capture the entire spirit of rock and roll in that short burst of sound. It’s pure adrenaline.
7. It’s So Easy (1958)
“It’s So Easy,” released in 1958, might sound carefree on the surface, but there’s real magic in its simplicity. From the first bouncy guitar riff, you know you’re in Buddy Holly territory—bright, catchy, and straight from the heart. The song taps into the bliss of love that feels effortless and natural. Holly sings with a laid-back confidence, his voice gliding over the upbeat tempo like a summer breeze. “It’s so easy to fall in love,” he repeats, as if even he can’t believe how good it feels.
But underneath that breezy exterior is a masterful composition. The tight rhythm section, the clean guitar licks, and Holly’s playful phrasing all come together to create something deceptively polished. This isn’t just a feel-good track—it’s one of those songs that sticks with you, sneaking into your head when you least expect it. And that’s part of its genius. Holly had a knack for making songs that sounded effortless, even though there was real craftsmanship behind them.
Over the years, “It’s So Easy” has been covered by everyone from Linda Ronstadt to The Crickets themselves, and it’s easy to see why—it’s universal, infectious, and just plain fun.
8. Maybe Baby (1958)
“Maybe Baby,” released in 1958, is a shining example of Buddy Holly’s ability to channel complex emotions into upbeat, memorable music. On the surface, it’s a playful love song about the uncertainty of romance—but dig a little deeper, and there’s a touch of melancholy beneath the catchy rhythm. The track opens with that unmistakable guitar riff, instantly setting a tone that’s equal parts hopeful and wistful. Holly’s vocals are smooth and sincere, bouncing between confidence and longing as he wonders whether his love will be returned.
The lyrics are beautifully straightforward: “Maybe baby, I’ll have you / Maybe baby, you’ll be true.” It’s the kind of song that anyone who’s ever nursed a crush or hoped for love can relate to. The backing harmonies, provided by The Crickets, add a rich texture to the sound, giving it that signature Buddy Holly flavor—clean, layered, and deeply melodic.
What’s so special about “Maybe Baby” is that it captures the rollercoaster of young love without being melodramatic. It’s hopeful, yes—but it also understands the sting of uncertainty. That emotional honesty, wrapped in a toe-tapping rock and roll package, is what makes this song a timeless classic.
9. Words of Love (1957)
“Words of Love,” released in 1957, offers a quieter, more contemplative side of Buddy Holly. Unlike many of his more upbeat hits, this song is a soft, romantic ballad that leans into tenderness over energy. It’s a love song that feels personal and hushed, almost like a whispered secret. Holly’s vocals are warm and dreamy, and the lyrics speak to the power of heartfelt communication: “Words of love, soft and true / Spoken by you.”
What makes the track especially remarkable is Holly’s innovative use of overdubbing—he harmonized with himself, layering his vocals to create a rich, echoing sound that was groundbreaking for the time. This technique gave “Words of Love” an ethereal, almost otherworldly quality that stood out from the crowd. The guitar is gentle, the rhythm steady, and the overall mood is pure intimacy.
Although the song wasn’t a massive hit upon release, its beauty wasn’t lost on other musicians. The Beatles famously covered it on their Beatles for Sale album, a testament to Holly’s influence on their sound. “Words of Love” is a hidden gem in his catalog—a quiet, poetic moment that shows just how versatile and visionary Holly truly was.
10. True Love Ways (1960)
“True Love Ways” is perhaps Buddy Holly’s most emotional and mature song, recorded just months before his untimely death and released posthumously in 1960. Unlike his earlier rock-driven tracks, this one is a sweeping ballad, complete with lush orchestration, including strings and horns. It marks a striking evolution in Holly’s musical journey—a glimpse of the artist he was becoming. The lyrics are deeply romantic, promising enduring love through life’s ups and downs: “Just you know why / Why you and I / Will by and by / Know true love ways.”
Holly’s vocals are tender and full of vulnerability, revealing a side of him that fans hadn’t quite heard before. There’s a haunting beauty in the way he delivers each line—gentle, sincere, and entirely heartfelt. You can hear the influence of classic love standards, but Holly makes the sound his own with understated charm and grace.
The song has since become a favorite at weddings and memorials, a symbol of lasting devotion. Knowing it was one of the last songs he ever recorded adds a layer of poignancy that’s impossible to ignore. “True Love Ways” isn’t just a love song—it’s a farewell letter, wrapped in timeless melody.
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.
