Buddy Holly, the bespectacled legend of rock ‘n’ roll, left an indelible mark on the music world despite his tragically short career. With his infectious melodies, heartfelt lyrics, and innovative sound, Buddy Holly became one of the most influential artists of the 1950s, inspiring generations of musicians from The Beatles to Bruce Springsteen. His music didn’t just define an era—it transcended it, cementing his place as a trailblazer in rock history.
In this article, we’re diving into the top 10 most beloved Buddy Holly songs of all time. From toe-tapping rockabilly anthems to poignant ballads, these tracks showcase Holly’s extraordinary talent and the timeless appeal of his music. Whether you’re a lifelong fan or new to the magic of Buddy Holly, this list will take you on a journey through the songs that made him a household name and a cultural icon.
So, dust off your vinyl records, crank up the volume, and let’s celebrate the unforgettable hits that continue to prove why Buddy Holly’s music is as fresh and electrifying today as it was over six decades ago. Ready to rock? Let’s dive in!
1. “That’ll Be the Day” (1957)
Buddy Holly’s “That’ll Be the Day” is more than just a song—it’s a defining moment in rock ‘n’ roll history. Released in 1957 with his band The Crickets, the track became Holly’s breakthrough hit, launching him into stardom. Co-written by Holly and drummer Jerry Allison, the song was famously inspired by John Wayne’s catchphrase in The Searchers, where he would say, “That’ll be the day” with a sense of doubt and irony.
From the opening guitar strums, the song radiates a sense of swagger and confidence, with Holly’s signature hiccupping vocals adding an unmistakable charm. The upbeat, infectious rhythm, driven by twangy guitar licks and steady percussion, made it an instant classic. It was an anthem of youthful rebellion, love, and determination, encapsulating the energy of 1950s rock music.
The song soared to No. 1 on the Billboard Hot 100 and became one of the most recognizable rock songs of all time. Its influence reached far and wide, inspiring future legends like The Beatles, who cited Holly as a major influence. Even decades later, “That’ll Be the Day” remains a staple in rock history, proving that Buddy Holly’s music truly never fades away.
2. “Peggy Sue” (1957)
Few songs are as instantly recognizable as Buddy Holly’s “Peggy Sue.” Released in 1957, the track is a masterclass in rhythm and vocal delivery, showcasing Holly’s ability to turn a simple love song into something extraordinary. Originally titled “Cindy Lou” after his niece, the name was changed at the request of drummer Jerry Allison, who wanted to impress his girlfriend, Peggy Sue Gerron.
The song’s hypnotic rhythm is one of its standout features. Jerry Allison’s rapid, rolling drumbeat provides an almost heartbeat-like pulse, creating a mesmerizing effect that drives the entire track. Meanwhile, Holly’s vocals are dynamic and filled with longing, as he croons the now-iconic lines, “Oh, Peggy Sue / Oh, how my heart yearns for you.” His distinctive vocal hiccups and effortless phrasing add a sense of urgency and emotion, making the song unforgettable.
“Peggy Sue” became an instant hit, reaching No. 3 on the Billboard charts. It remains one of Holly’s most beloved songs, covered by numerous artists, including Elvis Presley and The Beach Boys. Decades later, its infectious melody and heartfelt lyrics continue to make it a standout in rock’s golden era.
3. “Everyday” (1957)
“Everyday” is one of Buddy Holly’s most delicate and heartfelt songs, proving that rock ‘n’ roll didn’t always need loud guitars and driving beats to make an impact. Released in 1957, this tender track showcases Holly’s softer side, capturing a sense of youthful optimism and romantic anticipation.
What makes “Everyday” so special is its simplicity. Instead of drums, the song uses handclaps and the gentle tapping of Jerry Allison’s fingers on his knee to create a steady rhythm. A celesta—an instrument with a bell-like tone—provides a dreamlike melody, adding to the song’s warmth and charm. Holly’s vocals are light and affectionate, perfectly matching the lyrics about love growing stronger with each passing day.
Though it wasn’t a major hit upon release, “Everyday” has become one of Holly’s most enduring songs, beloved for its innocence and sincerity. The track has been featured in countless movies, commercials, and cover versions, ensuring its place in music history. Whether it’s the tender lyrics or the song’s unique instrumentation, “Everyday” continues to resonate with listeners, proving that true love and great music are timeless.
4. “Oh Boy!” (1957)
Few songs capture the pure excitement of rock ‘n’ roll quite like “Oh Boy!” Released in 1957 by Buddy Holly and The Crickets, this high-energy anthem is an electrifying celebration of love and youthful enthusiasm. From the first note, the song bursts with energy, featuring punchy guitar riffs, a driving beat, and Holly’s signature vocal delivery that makes it impossible to sit still while listening.
Written by Sonny West, Bill Tilghman, and Norman Petty, “Oh Boy!” wasn’t originally meant for Holly, but once he recorded it, the song became his own. His exuberant voice, filled with joy and passion, transforms the lyrics into an irresistible expression of excitement. The chorus—“Oh boy, when you’re with me, oh boy / The world will see that you were meant for me”—feels like a declaration of young love at its most thrilling.
Upon release, the song became a fan favorite, reaching No. 10 on the Billboard charts. Over the years, “Oh Boy!” has remained a rock classic, covered by artists from The Beatles to Bruce Springsteen. Its infectious spirit and timeless charm continue to make it a staple of Holly’s legacy, reminding us why his music still feels fresh decades later.
5. “Not Fade Away” (1957)
“Not Fade Away” is one of Buddy Holly’s most influential songs, showcasing his ability to blend rock, blues, and rhythm into a timeless classic. Released in 1957, the song was built around the famous Bo Diddley beat, a driving rhythm that would later become a staple of rock music. With its pulsing percussion, jangly guitar, and hypnotic melody, “Not Fade Away” had a raw, infectious energy that set it apart.
Lyrically, the song carries a message of unwavering devotion: “My love’s bigger than a Cadillac / I try to show it and you’re drivin’ me back.” Holly’s delivery is playful yet determined, filled with the kind of youthful confidence that made his music so appealing. It was a different kind of love song—one that wasn’t just romantic, but also defiant and full of swagger.
Though it didn’t chart as highly as some of Holly’s other hits, “Not Fade Away” left a lasting impact. It was later famously covered by The Rolling Stones in 1964, helping to introduce Holly’s influence to a new generation. Even today, the song remains a testament to his enduring legacy, proving that great music, just like the title suggests, doesn’t fade away.
6. “Maybe Baby” (1958)
With its smooth harmonies and catchy melody, “Maybe Baby” is one of Buddy Holly’s most effortlessly charming songs. Released in 1958 with The Crickets, the track perfectly encapsulates the feeling of hopeful romance, where love is just within reach but not quite certain. Holly’s songwriting brilliance shines here, as he takes a simple theme and transforms it into something irresistibly memorable.
From the start, the song’s bouncing rhythm and twangy guitar set an upbeat tone, while Holly’s warm vocals convey both longing and excitement. The lyrics—“Maybe baby, I’ll have you / Maybe baby, you’ll be true”—express the uncertainty of love in a way that feels both personal and universal. There’s an innocent charm to the song, making it easy to relate to no matter the listener’s age.
“Maybe Baby” became one of The Crickets’ standout hits, helping solidify Holly’s reputation as a master of crafting simple yet impactful pop-rock songs. Over the years, it has remained a favorite among fans, covered by artists like Paul McCartney and Roy Orbison. Its lighthearted energy and undeniable catchiness make it a timeless classic in Holly’s remarkable catalog.
7. “Rave On” (1958)
Few songs capture the raw excitement of early rock ‘n’ roll as perfectly as “Rave On.” Released in 1958, this high-energy anthem is pure rock at its finest—fast-paced, electrifying, and bursting with enthusiasm. Written by Sonny West, Bill Tilghman, and Norman Petty, the song found its perfect match in Buddy Holly, whose spirited performance turned it into one of his most exhilarating hits.
Right from the start, “Rave On” grabs the listener’s attention with its driving rhythm, crisp guitar work, and Holly’s urgent vocals. His signature hiccupping delivery adds an extra layer of excitement, making the song feel like a celebration of love and music itself. The lyrics—“We’re gonna rave on and love until the early dawn”—perfectly encapsulate the rebellious, carefree spirit of 1950s rock.
Despite being just over two minutes long, “Rave On” leaves a lasting impression. It wasn’t a major hit upon release, but over time, it became one of Holly’s most beloved songs, covered by everyone from Bruce Springsteen to John Mellencamp. Today, it stands as a testament to Holly’s ability to infuse rock ‘n’ roll with both joy and urgency, ensuring his music still makes listeners want to get up and dance.
8. “It’s So Easy” (1958)
“It’s So Easy” is a breezy, feel-good rock ‘n’ roll tune that perfectly captures Buddy Holly’s effortless charm. Released in 1958, the song is deceptively simple, yet its catchy melody and laid-back groove make it one of Holly’s most enjoyable recordings. Written by Holly and Norman Petty, it’s a playful take on young love, where falling head over heels is as natural as breathing.
The song’s opening guitar riff immediately sets the tone—light, bouncy, and inviting. Holly’s smooth vocals add to the relaxed vibe as he sings, “It’s so easy to fall in love,” almost as if he’s making a carefree confession. The stripped-down arrangement, featuring jangling guitars and an easygoing rhythm, allows Holly’s voice to shine. While it didn’t make a major splash on the charts during his lifetime, the song gained recognition over time, especially after Linda Ronstadt’s 1977 cover turned it into a hit.
Despite its initial commercial underperformance, “It’s So Easy” has become a staple of Holly’s catalog. Its simplicity is its strength, proving that great rock ‘n’ roll doesn’t need to be overly complicated—it just needs to be heartfelt, fun, and unforgettable.
9. “True Love Ways” (1958)
“True Love Ways” is one of Buddy Holly’s most heartfelt and beautifully orchestrated ballads. Recorded in 1958 and written as a dedication to his wife, Maria Elena, the song stands out for its lush instrumentation and deeply personal lyrics. Unlike the upbeat rock ‘n’ roll tracks Holly was best known for, “True Love Ways” showcases a more mature and introspective side of his artistry.
The song’s arrangement is strikingly different from his usual guitar-driven sound. It features a sweeping string section, gentle piano, and subtle jazz influences that give it a timeless elegance. Holly’s vocals are rich and emotional, making every line feel like a sincere expression of devotion. Lyrics like “Just you know why / Why you and I / Will by and by / Know true love ways” convey a deep sense of commitment and understanding in a way that few love songs manage to achieve.
Tragically, “True Love Ways” was released posthumously after Holly’s untimely passing in 1959, adding even more weight to its emotional resonance. Over the years, the song has been covered by numerous artists, including Peter & Gordon and Cliff Richard, but Holly’s original version remains the most poignant. It’s a lasting testament to his ability to craft music that was not only innovative but also profoundly moving.
10. “Words of Love” (1957)
“Words of Love” is a beautifully crafted song that highlights Buddy Holly’s innovative spirit and deep understanding of melody. Released in 1957, it’s a delicate, dreamy ballad that stands apart from his more upbeat rock ‘n’ roll hits. Holly recorded the song using a groundbreaking technique at the time—overdubbing his own harmonies—which gave the track a unique, ethereal quality.
The song’s gentle guitar work and soft, layered vocals create an atmosphere of warmth and sincerity. The lyrics—“Words of love, you whisper soft and true / Darling, I love you”—are simple yet deeply affecting, making the song feel like an intimate confession of love. Though it wasn’t a major hit upon release, “Words of Love” showcased Holly’s ability to blend tenderness with innovation, proving that rock ‘n’ roll wasn’t just about energy—it could also be deeply poetic.
One of the biggest testaments to the song’s lasting influence came when The Beatles covered it in 1964, introducing it to an even wider audience. Their version stayed faithful to Holly’s original arrangement, a nod to just how ahead of his time he was. Today, “Words of Love” remains one of Holly’s most beloved songs, a quiet but powerful reminder of his genius and the lasting impact of his music.
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.
