Few voices in music history have the power to transport listeners to a world of elegance, romance, and soul-stirring emotion like Nat King Cole’s. A true icon of 20th-century music, Cole’s velvety baritone and effortless charm made him an international sensation, bridging genres and touching hearts across generations. From jazz clubs to concert halls, his songs have become timeless anthems of love and sophistication, cementing his legacy as one of the greatest vocalists of all time.
This article dives into the definitive list of Nat King Cole’s top 10 most popular songs—classics that continue to captivate audiences even decades after their release. Whether you’re a lifelong fan or new to his music, these songs are a testament to Cole’s unparalleled artistry and the enduring appeal of his smooth, heartfelt melodies. From the dreamy romance of “Unforgettable” to the timeless warmth of “The Christmas Song (Chestnuts Roasting on an Open Fire)”, these tracks are more than music—they’re moments frozen in time. So, get ready to rediscover the magic of Nat King Cole as we count down his most iconic hits, celebrating the songs that made him a legend in the world of music.
1. “Unforgettable” (1951)
“Unforgettable” is one of those songs that transcends time and place, remaining as deeply moving today as it was when it was first released in 1951. Nat King Cole’s velvety voice becomes a conduit for the song’s heartfelt lyrics, written by Irving Gordon. This timeless love ballad, with its lush orchestration and smooth delivery, has become synonymous with romance and devotion. Cole’s voice, with its warmth and depth, seems to effortlessly capture the essence of enduring love—one that stays with us long after the moment passes. The lyrics, simple but profound, convey the message that love leaves an indelible mark on the soul. It’s no surprise that “Unforgettable” has become a staple at weddings, anniversaries, and romantic gatherings. The song’s ability to evoke feelings of nostalgia and passion is unmatched, making it a classic that continues to hold an emotional grip on listeners, generation after generation. Whether it’s played during a quiet evening at home or at a celebration of love, “Unforgettable” remains the quintessential anthem for those in love, and its legacy continues to inspire and move people around the world.
2. “Mona Lisa” (1950)
“Mona Lisa” is more than just a song—it’s a masterpiece of both lyricism and delivery. Released in 1950, this Academy Award-winning track written by Ray Evans and Jay Livingston reveals Nat King Cole at his most introspective. The song takes its name from the famous painting by Leonardo da Vinci, but its lyrics evoke a sense of mystery and melancholy that mirrors the enigmatic smile of the Mona Lisa herself. Cole’s smooth, emotive delivery of these thoughtful words makes every line feel deeply personal, while the melody wraps around his voice like a comforting embrace. It’s a song that conveys longing, beauty, and a sense of quiet resignation—feelings that are universally understood. With its haunting, almost dreamlike quality, “Mona Lisa” remains one of the greatest love songs ever written, not for its overt passion, but for its ability to convey something deeper: a sense of the unknowable and the elusive. Cole’s understated, yet profoundly moving, vocal performance gives the song an enduring emotional weight, earning it a place in music history. Over the years, “Mona Lisa” has captivated generations of listeners, and it remains a timeless classic in the world of popular music.
3. “The Christmas Song (Chestnuts Roasting on an Open Fire)” (1946)
Few holiday songs capture the magic and warmth of the season as beautifully as Nat King Cole’s rendition of “The Christmas Song.” First recorded in 1946, this holiday classic, written by Mel Tormé and Bob Wells, has become synonymous with the Christmas season. Cole’s deep, soothing voice brings the lyrics to life with a gentle nostalgia, painting a picture of cozy nights by the fire and the joy of family gatherings. The imagery of “chestnuts roasting on an open fire” evokes a sense of comfort, while Cole’s calm delivery gives the song a serene, almost timeless quality. The rich orchestration adds an additional layer of warmth, making it a track that, year after year, feels like an old friend returning to spread holiday cheer. While many artists have covered this Christmas staple, it’s Cole’s version that remains the definitive one. His voice carries the spirit of Christmas in a way that feels both intimate and universal. Whether it’s playing in the background during holiday preparations or as the soundtrack to quiet moments of reflection, “The Christmas Song” is a song that never grows old. It continues to capture the heart of what makes Christmas so special: togetherness, warmth, and the simple joys of the season.
4. “L-O-V-E” (1965)
Released in 1965, “L-O-V-E” is a perfect example of Nat King Cole’s playful side, showcasing his ability to bring joy and charm to his music. This jazzy, upbeat tune is a celebration of love in its simplest, most straightforward form, and Cole’s joyful delivery adds an infectious energy to the track. The song’s catchy melody and playful rhythm make it an instant favorite, while the clever lyrics spell out “L-O-V-E” in a way that feels both fun and romantic. It’s one of those rare songs that immediately makes you smile—Cole’s voice, as smooth as ever, delivers each word with a wink and a nod. The track’s light-hearted nature belies its universal message about love’s power, making it not just a romantic tune but a celebration of affection in all its forms. The upbeat jazz-pop sound paired with Cole’s effortless vocal style gives “L-O-V-E” a timeless quality that resonates across generations. Even decades after its release, this song continues to be a crowd-pleaser, often featured in romantic comedies and as a feel-good anthem at weddings and parties. “L-O-V-E” is more than just a song—it’s an invitation to embrace love in all its joyful, beautiful simplicity.
5. “Nature Boy” (1948)
“Nature Boy” is a song that lingers in your mind long after the last note fades. First recorded by Nat King Cole in 1948, this hauntingly beautiful track, written by eden ahbez, offers a glimpse into the more philosophical side of love and life. With its ethereal melody and deeply introspective lyrics, “Nature Boy” tells the story of a young man who lives by his own unique set of values—one that revolves around love, wonder, and the natural world. The song’s philosophical undertones give it a timeless quality, allowing it to speak to listeners from all walks of life, regardless of era. Nat King Cole’s voice, as rich and smooth as ever, brings a sense of reverence to the song, elevating it into something truly magical. The simple yet profound lyrics—“The greatest thing you’ll ever learn / Is just to love and be loved in return”—have the power to resonate deeply, offering a universal truth about the human experience. Cole’s tender performance gives the song a timeless emotional depth, making it not just a classic, but a deeply meaningful piece of art that remains as impactful today as it was when it was first recorded.
6. “Straighten Up and Fly Right” (1944)
“Straighten Up and Fly Right” is a playful and upbeat track that captures the spirit of Nat King Cole’s early jazz career. Released in 1944, the song is based on a folk tale told by Cole’s father, and its clever lyrics carry a message of wisdom wrapped in humor. The track’s lively rhythm and catchy melody make it an instant toe-tapper, while its simple yet profound message reminds us to stay focused and on the right path. The song’s playful tone is balanced by its smooth, swing-influenced jazz instrumentation, which gives it a timeless quality. Nat King Cole’s vocal performance here is both charming and authoritative—he delivers the advice with a sense of fun, but also with the calm assurance of someone who knows what they’re talking about. “Straighten Up and Fly Right” captures the optimism and carefree energy of the swing era, and its upbeat nature makes it an enduring favorite. Whether you’re a fan of classic jazz or simply appreciate great storytelling, this song’s infectious melody and timeless message will lift your spirits every time you hear it.
7. “Too Young” (1951)
“Too Young” is a beautiful, bittersweet ballad that captures the innocence and uncertainty of young love. Released in 1951, the song quickly became one of Nat King Cole’s biggest hits, showcasing his ability to convey both tenderness and longing with ease. The lyrics tell the story of a love that, despite its sweetness, is doomed by the age and inexperience of its participants. Yet, there’s an underlying optimism that suggests love, no matter how fleeting, is always worth the effort. Cole’s voice, as velvety and warm as ever, effortlessly captures the vulnerability of youth, making the song resonate with anyone who has ever loved for the first time. The smooth orchestration pairs perfectly with Cole’s delicate vocal delivery, enhancing the song’s emotional impact. “Too Young” stands as one of those timeless classics that speaks directly to the heart, making it a favorite for listeners of all ages. The track’s universal theme—of love that is pure yet untested—has made it an enduring favorite, and it continues to evoke a sense of nostalgia and longing every time it is played.
8. “When I Fall in Love” (1956)
“When I Fall in Love” is one of the most quintessential romantic ballads in music history. Released in 1956, this timeless song captures the vulnerability and hope of falling deeply in love. Nat King Cole’s delivery is full of tenderness, with each note reflecting the warmth and sincerity of the lyrics. The lush orchestration swells beneath his voice, creating a soundscape that perfectly complements the sentiment of the song. The lyrics, which express the longing to find a love that is lasting and true, resonate deeply with anyone who has ever experienced the joy and fear that comes with opening your heart to someone. The song builds slowly, reaching its emotional peak with Cole’s powerful declaration that love, when it comes, will be the most beautiful thing in the world. “When I Fall in Love” has become a staple at weddings and romantic occasions, thanks to its universal message about the power of love. It’s a song that captures the timeless nature of love itself—a feeling that never grows old and always feels as fresh as the first time you fall in love.
9. “Smile” (1954)
Originally composed by Charlie Chaplin for his film Modern Times, “Smile” took on new depth when Nat King Cole recorded it in 1954. The song’s message is simple yet profound: even in the face of hardship, there is power in finding joy and resilience. Cole’s voice gives the song an added layer of emotional weight, imbuing the lyrics with a sense of optimism that feels both soothing and uplifting. The orchestration, subtle yet sweeping, complements Cole’s soothing delivery, creating a sense of peace and comfort for the listener. The line “You’ll find that life is still worthwhile if you just smile” has become an enduring mantra for many, reminding us that even in our darkest moments, there is always a reason to find joy. “Smile” is a song that offers both comfort and inspiration, with its hopeful message shining through every note. Cole’s interpretation of the song elevates it beyond its original context, making it a universal anthem for resilience and positivity. Decades after its release, “Smile” remains a timeless classic, one that continues to inspire listeners to face life’s challenges with grace and a smile.
10. “Route 66” (1946)
“Route 66” is a song that exudes adventure and freedom, capturing the essence of the iconic American highway. First recorded by Nat King Cole in 1946, this upbeat tune is a perfect example of the band’s swing-era jazz influences, blending a driving rhythm with playful lyrics. Written by Bobby Troup, the song paints a picture of a road trip through the American heartland, evoking feelings of wanderlust and exploration. Cole’s jazzy rendition gives the song an infectious energy, while his smooth, effortless vocals bring the lyrics to life with a sense of fun and excitement. The catchy melody and rhythm make it an enduring favorite for those who love the open road and the freedom it represents. “Route 66” is more than just a travel song—it’s a celebration of the spirit of adventure, and Cole’s performance breathes life into Troup’s words. Even today, this track remains a quintessential anthem for road-trippers and those with a love for the journey. Whether you’re setting off on a cross-country adventure or simply daydreaming of a future road trip, “Route 66” continues to spark the wanderlust in all of us.
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.
