Few voices in music history possess the power to transcend decades, cultures, and generations like that of Nat King Cole. A trailblazing artist whose velvety baritone and impeccable artistry defined an era, Cole’s music remains a cornerstone of jazz and pop standards. With a career spanning over three decades, he enchanted audiences with his smooth vocals, heartfelt lyrics, and effortless charm, leaving an indelible mark on the world of music.
From soulful ballads to lively swing tunes, Nat King Cole’s songs capture the essence of love, loss, and joy with unmatched elegance. Whether you’ve danced to the romantic strains of “Unforgettable” or found solace in the tender notes of “Mona Lisa,” his music speaks to the heart and soul. But which of his timeless classics have stood the test of time as the most popular?
In this article, we celebrate the extraordinary legacy of Nat King Cole by counting down his top 10 most beloved songs of all time. Each track is a masterpiece in its own right, a testament to the enduring appeal of his artistry. Get ready to rediscover the magic of a legend whose music continues to inspire and captivate listeners worldwide.
1. “Unforgettable” (1951)
“Unforgettable” is one of those rare songs that truly lives up to its title. Released in 1951, it quickly became one of Nat King Cole’s signature pieces, offering a sublime blend of timeless romance and vocal perfection. Written by Irving Gordon, the lyrics express deep admiration and love, beautifully brought to life by Cole’s velvety, expressive voice. The lush orchestral backing adds a rich, emotional layer, wrapping the listener in warmth and nostalgia. What sets this song apart is not just its romantic message, but the sincerity with which Cole delivers every line—it feels personal, like a private serenade meant just for you. “Unforgettable” has remained a staple at weddings, anniversaries, and romantic moments for over seven decades, resonating with listeners of all ages. Its legacy was renewed in 1991 when Cole’s daughter, Natalie Cole, released a virtual duet with her father, introducing the classic to a new generation. That version, too, won numerous accolades and hearts. Whether you hear the original or the duet, “Unforgettable” continues to be exactly what the name suggests—an everlasting tribute to love and memory that never fades from the hearts of those who hear it.
2. “Mona Lisa” (1950)
Released in 1950, “Mona Lisa” is one of Nat King Cole’s most captivating and enduring songs. Written by the songwriting team of Ray Evans and Jay Livingston, the tune won the Academy Award for Best Original Song and became a number one hit, cementing Cole’s reputation as one of the era’s most enchanting vocalists. Inspired by Leonardo da Vinci’s iconic painting, the lyrics muse on the mystery and beauty hidden behind a smile. Cole’s delivery is flawless—subtle, smooth, and full of emotion. His voice seems to gently float over the delicate piano and string arrangements, creating a serene and reflective atmosphere. What makes “Mona Lisa” stand out is how effortlessly Cole brings a sense of human depth to a song that could’ve felt distant or abstract. Instead, it feels like a quiet conversation with a work of art. The song’s popularity soared, and it remains a favorite not just among Nat King Cole fans, but among lovers of classic ballads. “Mona Lisa” continues to inspire cover versions and has even found its way into films and TV, proving that the mystery of that smile—and the beauty of Cole’s voice—still holds sway today.
3. “The Christmas Song (Chestnuts Roasting on an Open Fire)” (1946)
Few holiday songs have the staying power or warmth of “The Christmas Song,” also fondly known by its opening line, “Chestnuts roasting on an open fire.” Originally recorded by Nat King Cole in 1946, the song was written by Mel Tormé and Bob Wells during a hot summer as a way to imagine cooler, festive days. But it was Cole’s voice—rich, smooth, and comforting—that turned the tune into a timeless Christmas standard. With sweeping strings and a soft piano accompaniment, the arrangement wraps around listeners like a cozy blanket. Cole’s phrasing is effortless, and his delivery captures the magic and nostalgia of the holiday season. The song paints vivid imagery of wintry scenes and family togetherness, making it a staple on radio stations, in shopping malls, and in living rooms around the world every December. Over the years, it’s been covered by countless artists, but Nat King Cole’s version remains the gold standard. It’s more than just a song—it’s a feeling, a memory, a moment that returns each year to fill hearts with joy and sentiment. “The Christmas Song” is, quite simply, the sound of Christmas for millions.
4. “Nature Boy” (1948)
“Nature Boy” stands out in Nat King Cole’s catalog as one of his most mysterious and profound recordings. Released in 1948, the song was written by the enigmatic eden ahbez, a proto-hippie who lived off the grid and believed in living in harmony with nature. His philosophical lyrics tell the story of a “strange, enchanted boy” who teaches that “the greatest thing you’ll ever learn is just to love and be loved in return.” The haunting melody and orchestration evoke a dreamlike quality, and Cole’s tender, contemplative delivery makes the message resonate even more deeply. Unlike some of his more polished, romantic ballads, “Nature Boy” feels almost spiritual—otherworldly in its beauty. It was a surprising hit at the time, climbing to the top of the charts, and it remains a favorite for its depth and originality. The song’s meditative tone and gentle wisdom have inspired many artists across generations to reinterpret it, yet none quite match the subtle power of Cole’s version. “Nature Boy” is more than just a song; it’s a poetic reflection on love, life, and the human journey, carried on the wings of Nat King Cole’s unforgettable voice.
5. “Too Young” (1951)
“Too Young,” released in 1951, became one of Nat King Cole’s biggest hits and a defining moment in his career. Written by Sylvia Dee and Sidney Lippman, the song touches on the tender and sometimes painful realities of young love. Its lyrics reflect the skepticism often faced by couples who are told they’re not mature enough to understand true love, despite what they feel in their hearts. Cole delivers the song with aching sincerity and emotional restraint, allowing the gentle piano and string accompaniment to highlight the vulnerability in his voice. His performance struck a powerful chord with listeners, especially younger audiences who related to the message. The song soared to the top of the Billboard charts and became the biggest hit of 1951, reinforcing Cole’s reputation as a vocalist who could connect with deep emotional truths. Even decades later, “Too Young” resonates with anyone who has ever felt dismissed or misunderstood in matters of the heart. It’s a beautifully understated ballad that captures the timeless nature of love and the quiet strength of believing in your own feelings, no matter what others may say.
6. “L-O-V-E” (1965)
“L-O-V-E” is one of Nat King Cole’s most joyful and infectious songs, showing off his playful side and impeccable phrasing. Released in 1965, this jazzy number was written by Bert Kaempfert and Milt Gabler, and it quickly became a standout in Cole’s catalog. With a swinging big-band arrangement and clever lyrics that spell out the word “love,” the track feels like a celebration from start to finish. Cole’s delivery is smooth, charismatic, and full of personality—he makes every note dance. It’s the kind of song that instantly lifts your spirits and gets your feet tapping. Although it was one of the last singles Cole recorded before his untimely death, “L-O-V-E” feels anything but final—it’s vibrant and full of life. The tune has become a popular choice at weddings, parties, and romantic events, embodying both elegance and fun. Over the years, it’s been covered by numerous artists in multiple languages, but Nat King Cole’s original remains the definitive version. “L-O-V-E” is proof of how Cole could make even the simplest phrase sound sophisticated, and it continues to charm audiences all over the world with its timeless groove.
7. “Smile” (1954)
“Smile” is one of Nat King Cole’s most poignant and emotionally resonant performances. Released in 1954, the song is based on a haunting melody composed by Charlie Chaplin for his 1936 film Modern Times. With lyrics later added by John Turner and Geoffrey Parsons, “Smile” encourages hope and resilience even in the face of sorrow. Nat King Cole’s version elevates the song into a timeless ballad of quiet strength and optimism. His voice carries a tender warmth that gently urges listeners to hold on through life’s difficult moments. The orchestral arrangement is understated but lush, allowing the sincerity in Cole’s voice to shine through. There’s a subtle ache beneath the song’s encouraging message—something that only Cole’s nuanced delivery could convey so gracefully. “Smile” reminds us that even through tears, there can be light, and that hope often lives in the smallest gestures. Over the decades, it has become a universal anthem of comfort, sung to those in pain, grief, or struggle. Nat King Cole didn’t just sing “Smile”—he embodied it, making the message unforgettable. His rendition continues to inspire, offering solace with every listen and serving as a quiet reminder to keep going, no matter what.
8. “Straighten Up and Fly Right” (1943)
“Straighten Up and Fly Right” marked a major turning point in Nat King Cole’s early career. Released in 1943 with the King Cole Trio, the song was co-written by Cole and lyricist Irving Mills, inspired by a folk tale Cole’s father, a Baptist preacher, used in his sermons. The tune blends humor and moral advice with an irresistible swing rhythm. It tells the story of a buzzard trying to trick a monkey—until the monkey calls his bluff. Packed with witty metaphor and clever wordplay, the lyrics make a case for personal integrity and living right, all delivered with style and flair. Cole’s piano playing is crisp and infectious, while his vocal performance is full of charm and energy. The song became a massive hit and helped Cole cross over from jazz clubs to mainstream success. It showcased not only his musical talent but also his charisma and storytelling skills. “Straighten Up and Fly Right” still feels fresh, thanks to its lively tempo and universal message. It’s a song with a groove and a lesson, and a perfect example of how Cole blended musical excellence with wit and wisdom in equal measure.
9. “Route 66” (1946)
“Route 66,” released in 1946, is a spirited celebration of travel, adventure, and classic Americana. Written by Bobby Troup, the song follows the famous highway stretching from Chicago to Los Angeles, naming cities along the way and inviting listeners to take the journey. Nat King Cole’s recording with the King Cole Trio was the first and remains one of the most iconic versions. With its swing-infused rhythm, sharp piano lines, and laid-back vocals, Cole turned a simple road map into a joyful musical ride. His voice exudes coolness and confidence, effortlessly gliding over the catchy lyrics. The trio’s tight musicianship gives the song a toe-tapping energy that captured the postwar spirit of mobility and freedom. “Route 66” quickly became a hit and a signature tune for Cole, paving the way for future covers by artists in rock, jazz, and blues. It remains a staple in American music history, often associated with the idea of hitting the open road and chasing dreams. Nat King Cole gave the song its unforgettable swagger, making it more than just a travel anthem—it became a symbol of opportunity and timeless swing.
10. “When I Fall in Love” (1956)
“When I Fall in Love” is one of the most romantic songs Nat King Cole ever recorded. Released in 1956, the ballad was written by Victor Young and Edward Heyman and has since become a standard for declarations of deep, enduring love. Cole’s version is particularly cherished because of its emotional honesty and gentle beauty. His voice, smooth and velvety, delivers each line with grace and sincerity, as if he’s baring his soul to the listener. The lush orchestral arrangement adds to the song’s sweeping sense of romance, but it never overwhelms the vocal—it simply enhances the mood. The lyrics speak of a love that is pure and lifelong, something that only happens once and must be cherished. Cole’s delivery makes that vision feel possible. The song has been covered many times, but Nat King Cole’s rendition is widely regarded as definitive, and for good reason. It continues to be played at weddings, anniversaries, and romantic milestones, offering a heartfelt reminder of what true love can be. “When I Fall in Love” is more than just a love song—it’s a promise set to music, made eternal by Cole’s unforgettable voice.
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.
