Nat King Cole, a name synonymous with elegance, charm, and musical brilliance, has left an indelible mark on the world of music. From his velvety voice to his impeccable piano skills, Cole’s artistry transcends generations, making him one of the most beloved artists of all time. Whether you grew up listening to his soulful ballads or recently discovered his enchanting melodies, Nat King Cole’s music has a unique ability to transport listeners to a world of romance, nostalgia, and pure emotion.
In this article, we celebrate the top 10 most popular Nat King Cole songs of all time, a collection of timeless classics that have shaped the soundtrack of countless lives. From dreamy love ballads to swing-infused hits, these songs showcase the extraordinary talent and versatility of a man who redefined vocal jazz and pop music. Each track is a masterpiece, capturing the essence of a bygone era while remaining remarkably relevant today.
So, prepare to immerse yourself in the golden age of music as we count down the most iconic tracks of Nat King Cole’s illustrious career. Whether you’re a lifelong fan or a newcomer to his magic, this list promises to be a delightful journey through the heart and soul of one of music’s greatest legends.
1. Unforgettable (1951)
“Unforgettable” is one of those rare songs that truly lives up to its name. Written by Irving Gordon and brought to life by Nat King Cole in 1951, it’s a ballad that speaks straight to the heart. From the moment Cole begins to sing, his rich, velvety voice wraps around you like a warm embrace. The orchestration is elegant and understated, allowing the emotion in his voice to shine through. Lyrically, the song celebrates a love so deep and genuine that no time or distance could ever erase its impact. It’s the kind of romance that doesn’t fade—it lingers in the memory, carved into the soul. Cole’s performance is restrained yet profoundly expressive, striking the perfect balance between sentimentality and sincerity. “Unforgettable” quickly became a defining piece of his career and has since been embraced by generations of listeners. Its legacy only deepened when his daughter Natalie Cole recorded a virtual duet with her father in 1991, introducing the classic to a new audience. Whether it’s playing at a wedding or softly echoing through a quiet evening, “Unforgettable” continues to evoke the timeless beauty of true love remembered.
2. Mona Lisa (1950)
There’s a quiet elegance to “Mona Lisa” that has allowed it to endure for decades. Recorded by Nat King Cole in 1950, the song is a poetic reflection on enigmatic beauty, much like the painting it’s named after. Written by Ray Evans and Jay Livingston for the film Captain Carey, U.S.A., it immediately struck a chord with audiences and critics alike, going on to win the Academy Award for Best Original Song. Cole’s delivery is gentle and contemplative, filled with wonder and longing. His voice carries a sense of admiration tinged with melancholy, as if he’s trying to solve the mystery of someone who is forever just out of reach. The melody is hauntingly beautiful, and the orchestration supports Cole’s vocals with a soft, romantic glow. “Mona Lisa” became one of his signature songs, and its subtle, emotional power still resonates. It’s not a flashy tune, but that’s what makes it so captivating—it invites you to lean in and listen, to feel the emotion between the lines. In the hands of Nat King Cole, “Mona Lisa” isn’t just a song—it’s a portrait painted in sound, quietly mesmerizing.
3. The Christmas Song (1946)
Few songs capture the cozy magic of the holiday season quite like “The Christmas Song.” Written in 1946 by Mel Tormé and Bob Wells during a blistering summer heatwave, the song was meant to evoke wintry images—and it does so brilliantly. When Nat King Cole recorded it that same year, his warm, soothing voice gave the song a timeless quality that turned it into an instant classic. The opening line—“Chestnuts roasting on an open fire”—has become synonymous with Christmas, conjuring up scenes of family gatherings, snowy evenings, and heartfelt traditions. Cole’s phrasing is gentle and inviting, like a fireside storyteller sharing memories that never grow old. Over the years, the song has been covered by countless artists, but Cole’s rendition remains the gold standard. It strikes the perfect balance between sentiment and sophistication, never feeling overly sweet or forced. “The Christmas Song” is more than just seasonal background music—it’s a nostalgic journey that touches something deeply human. Every December, it returns like a dear old friend, reminding us that the best parts of the holidays are not the gifts or the glitter, but the warmth of love and togetherness.
4. L-O-V-E (1965)
“L-O-V-E” is a sparkling burst of joy from Nat King Cole’s later career. Released in 1965, the song was written by Bert Kaempfert and Milt Gabler and quickly became one of Cole’s most internationally recognized hits. With its playful structure—spelling out the word “love” letter by letter—it has a catchy, whimsical charm that’s hard to resist. The track leans heavily into jazz and swing influences, with a big band arrangement that snaps with energy and polish. Cole’s delivery is full of charisma and fun, showing off a lighter side of his artistry. While many of his songs are known for their emotional depth, “L-O-V-E” is pure celebration—breezy, flirtatious, and ideal for dancing or simply brightening your day. What makes it special is how effortlessly Cole elevates even the most cheerful tunes with his smooth, precise phrasing and innate musicality. Over the years, the song has been used in films, commercials, and countless romantic montages, proving its enduring appeal. “L-O-V-E” isn’t just a catchy tune—it’s a timeless declaration of affection, served up with sophistication and style. With Cole at the mic, every letter spells out a reason to smile.
5. Nature Boy (1948)
“Nature Boy” is a song unlike any other in Nat King Cole’s catalog—a haunting, mystical piece that feels almost otherworldly. Written by eden ahbez and recorded by Cole in 1948, the song blends elements of jazz, folk, and philosophical poetry into a brief but unforgettable meditation on life and love. The lyrics tell the story of a “strange, enchanted boy” who shares a profound truth: “The greatest thing you’ll ever learn is just to love and be loved in return.” It’s a message that’s both simple and deeply profound, and Cole delivers it with a quiet intensity that draws you in. His voice floats over a sparse, dreamy arrangement that enhances the song’s ethereal quality. “Nature Boy” was a bold departure from standard pop fare at the time, but its success proved the power of a song with soul and substance. It topped the charts and became one of Cole’s defining hits, helping to elevate his career to new heights. Even decades later, the song continues to resonate—its message timeless, its melody hauntingly beautiful. “Nature Boy” is not just a tune, but a whispered truth wrapped in music.
6. Too Young (1951)
“Too Young” is a tender ballad that speaks to the innocence and depth of young love—a theme that resonated powerfully with audiences when Nat King Cole recorded it in 1951. Written by Sidney Lippman and Sylvia Dee, the song tells the story of two people in love whose feelings are dismissed by others as immature or premature. But instead of rebelling or protesting, the lyrics gently insist on the sincerity of that affection, making a quiet yet powerful case for the legitimacy of young hearts. Cole’s performance is heartbreakingly sincere. His voice carries both a delicate vulnerability and quiet strength, giving weight to each word. The lush orchestration adds to the emotional gravity of the piece without overwhelming it, allowing the message of the song to shine through clearly. “Too Young” became a massive hit—so much so that it topped the charts and remained one of Cole’s best-selling singles. It struck a chord with listeners of all ages, especially younger fans who saw their own experiences reflected in its lyrics. Even today, the song remains a moving reminder that love doesn’t require years to be real—only honesty and feeling.
7. Straighten Up and Fly Right (1943)
“Straighten Up and Fly Right” is a lively, toe-tapping tune that marked a pivotal moment in Nat King Cole’s early career. Released in 1943 and co-written by Cole and lyricist Irving Mills, the song was inspired by a folk tale Cole had heard from his preacher father. The story of a monkey and a buzzard forms the song’s clever metaphor, delivering a moral lesson with charm and wit. Musically, the track is a swinging blend of jazz, jump blues, and early R&B, and it showcases Cole’s signature blend of smooth vocals and crisp piano work. It was a huge commercial success and helped catapult Cole from jazz clubs into mainstream popularity. More than just a catchy tune, “Straighten Up and Fly Right” carried cultural significance—it was fresh, fun, and full of personality at a time when audiences were hungry for something new. Its rhythmic bounce and sharp lyrics made it instantly memorable, and Cole’s charisma made it irresistible. Over time, the song has been covered by numerous artists, but none quite capture the original’s blend of sass and soul. For Nat King Cole, it was the song that truly helped him take flight.
8. When I Fall in Love (1956)
“When I Fall in Love” is a tender and timeless ballad that captures the delicate hopes and quiet vows that come with true romance. Written by Victor Young with lyrics by Edward Heyman, the song has been recorded by many greats over the years, but Nat King Cole’s 1956 rendition stands among the most iconic. His voice is calm and confident, yet tinged with the kind of emotional honesty that makes the listener believe every word. The arrangement is graceful, never overpowering—just a soft bed of strings that allows Cole’s vocals to take center stage. The lyrics are simple yet profound, reflecting a heartfelt belief that love should be enduring and genuine, not taken lightly or given away casually. Cole’s interpretation captures this spirit perfectly, making it feel like both a personal confession and a universal truth. “When I Fall in Love” became one of his most beloved recordings, a staple at weddings and romantic occasions ever since. It’s not just a song about love—it’s about commitment, trust, and the quiet longing for something real. In Nat King Cole’s voice, it becomes a promise set to music.
9. Smile (1954)
“Smile” is a deeply emotional ballad that reminds listeners to hold on to hope even in the midst of pain. Originally composed by Charlie Chaplin for his 1936 film Modern Times, the melody had no lyrics until 1954, when John Turner and Geoffrey Parsons added words to Chaplin’s bittersweet tune. Nat King Cole’s recording of “Smile” that same year gave the song its emotional wings. His voice, smooth and reassuring, carries the weight of the lyrics with quiet dignity. “Smile though your heart is aching…”—those first words carry a lifetime of feeling. Cole doesn’t oversell the sentiment; instead, he gently delivers each line, allowing the listener to fill in their own sorrow and find solace. The song has been described as a lullaby for adults, a soothing reminder that even in sadness, there’s light on the horizon. It resonated especially in postwar America, when people were searching for comfort and resilience. Cole’s version remains the definitive one—hopeful without being naïve, melancholy without being bitter. “Smile” is a beautiful contradiction: a song about sadness that somehow makes us feel better. And in Cole’s hands, it becomes pure emotional grace.
10. Route 66 (1946)
“Route 66” is a rollicking tribute to the open road and one of the earliest songs to capture the spirit of American travel. Written by Bobby Troup in 1946, the song takes listeners on a musical road trip from Chicago to Los Angeles, rolling through iconic towns and landmarks along the famous highway. Nat King Cole and his trio were the first to record it that same year, and their version set the tone for every cover that followed. With its infectious swing rhythm and Cole’s cool, confident vocals, “Route 66” became a jazz and rhythm & blues staple almost overnight. The song’s relaxed groove and vivid lyrics made it irresistible to postwar audiences dreaming of freedom and adventure. Cole’s piano work adds an extra layer of energy, propelling the track forward like a car speeding down the highway. Unlike some of his more sentimental ballads, “Route 66” is pure fun—stylish, upbeat, and endlessly replayable. It’s the sound of the open road, full of possibility and excitement. Cole’s version gave voice to a new kind of American optimism, and over the years, it’s remained the ultimate road trip anthem.
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.
