Nat King Cole, a timeless icon of jazz and pop, enchanted audiences with his velvety voice and unparalleled piano skills. Emerging in the 1940s, he transformed the music scene, blending genres and captivating hearts with his smooth melodies and heartfelt lyrics. From romantic ballads to swinging jazz numbers, Cole’s musical prowess knows no bounds, making him one of the most beloved artists of the 20th century.
In this article, we celebrate the top 10 most popular Nat King Cole songs of all time, each a masterpiece that showcases his extraordinary talent and emotional depth. Whether you’re a long-time fan or new to his enchanting sounds, these tracks offer a journey through Cole’s illustrious career, reflecting the essence of love, longing, and joy.
Join us as we explore the songs that not only defined an era but continue to resonate with listeners today. From the unforgettable “Unforgettable” to the soulful “Mona Lisa,” each selection is a testament to Cole’s lasting impact on music. Prepare to be transported to a world of smooth jazz and classic romance, as we dive into the melodies that have made Nat King Cole a cherished legend.
1. Unforgettable (1951)
“Unforgettable” remains one of Nat King Cole’s most iconic and emotionally resonant songs. With its silky orchestration and Cole’s effortlessly smooth vocals, this ballad captures the essence of a love that leaves an indelible mark on the heart. The lyrics are tender and sincere, painting a picture of a person who has become so intertwined with another’s life that forgetting them is simply impossible. The arrangement is elegant and understated, allowing Cole’s voice to shine as the centerpiece of the song. It’s no wonder that “Unforgettable” has become a favorite at weddings, anniversaries, and other moments of deep emotional significance. The song’s enduring popularity also speaks to Cole’s unparalleled ability to convey sentiment without ever sounding forced. Each phrase is delivered with warmth and poise, inviting the listener into a deeply personal space of memory and affection. It’s not just a romantic song—it’s a musical portrait of timeless devotion. Even decades after its release, “Unforgettable” continues to resonate across generations, reminding us that true love doesn’t fade—it becomes part of who we are.
2. The Christmas Song (Chestnuts Roasting on an Open Fire) (1946)
Nat King Cole’s version of “The Christmas Song” has become the definitive soundtrack to the holiday season. With its cozy, nostalgic imagery—chestnuts roasting, Jack Frost nipping, and carols being sung by a choir—the song evokes the magic and warmth of Christmas like few others can. Cole’s voice is rich and inviting, like a comforting fire on a cold winter night. His phrasing adds a sense of intimacy, making it feel as if he’s singing just for you in a quiet living room surrounded by family. The soft piano and string backing enhance the tender mood, creating a perfect sonic setting for reflection, joy, and togetherness. Though it has been covered by many artists over the decades, Cole’s rendition remains unmatched for its heartfelt delivery and timeless charm. More than just a seasonal tune, it taps into the universal desire for peace, love, and connection. Every December, when this song starts playing, it’s as though the entire world pauses to bask in its warmth. “The Christmas Song” isn’t just a holiday staple—it’s an enduring part of the season’s spirit.
3. Nature Boy (1948)
“Nature Boy” is one of Nat King Cole’s most enchanting and philosophical songs. With its ethereal melody and haunting orchestration, the song tells the story of a mysterious boy who wanders through life with a profound message: “The greatest thing you’ll ever learn is just to love and be loved in return.” The arrangement is sparse and atmospheric, which allows Cole’s voice to carry the narrative with a dreamlike intensity. The lyrics are poetic and symbolic, drawing listeners into a reflective space where the boundaries between reality and fable blur. Cole’s delivery is soft and reverent, treating the story with a sense of wonder and gravity. This isn’t just a song—it’s a quiet meditation on life, love, and wisdom. “Nature Boy” stood out as a bold artistic choice in its time, defying the norms of pop music and delving into the spiritual and philosophical. It still speaks to those who seek meaning beyond the surface, offering a sense of serenity and introspection. In Cole’s capable hands, the song becomes a gentle invitation to live with depth and compassion.
4. Smile (1954)
“Smile” is a tender reminder that even in life’s hardest moments, there’s strength in maintaining hope. Originally composed by Charlie Chaplin for the film Modern Times, the song was later given lyrics and transformed into a beloved standard. Nat King Cole’s interpretation is particularly moving—his soothing voice delivers each line with a quiet grace that feels like a personal encouragement. The orchestral arrangement is gentle and supportive, allowing the message to come through with clarity: smile, even when your heart is aching. Cole doesn’t oversell the emotion; instead, he allows the song to breathe, which makes its quiet optimism all the more powerful. “Smile” has become an anthem for resilience, often performed at tributes, memorials, and moments when comfort is most needed. What makes Cole’s version so enduring is the authenticity in his voice—he sounds like someone who’s lived through sadness but still chooses light. This song doesn’t promise that everything will be okay, but it gently nudges us to keep going. It’s a musical embrace, assuring us that grace can be found even in sorrow.
5. L-O-V-E (1965)
“L-O-V-E” is a sparkling gem in Nat King Cole’s discography—cheerful, jazzy, and brimming with charm. Unlike the introspective tone of many of his ballads, this track radiates joy and playfulness. From the moment the brass section bursts into action, the listener is swept up in a lively celebration of love’s simple pleasures. Cole spells out the word “love” in a fun and catchy way, giving each letter its own sweet meaning. His delivery is effortless and elegant, gliding over the upbeat rhythm with a wink and a smile. It’s no surprise that this song remains a popular choice at weddings, romantic dinners, and celebrations of all kinds. The arrangement swings with a carefree energy that’s contagious, and Cole’s vocal control is as precise as it is relaxed. “L-O-V-E” may be lighthearted, but it’s crafted with the sophistication of a seasoned performer who knows how to make every note count. This song is a reminder that love doesn’t always have to be serious—it can be light, playful, and absolutely delightful.
6. Mona Lisa (1950)
“Mona Lisa” is one of Nat King Cole’s most enduring and hauntingly beautiful ballads. Released in 1950, the song draws its inspiration from the enigmatic expression of da Vinci’s famous painting, using it as a metaphor for the mysteries of love and the guarded nature of the human heart. Cole’s velvet-smooth voice delivers the lyrics with an intimate tenderness, allowing the listener to feel the ache behind the question: Is she smiling because she’s in love, or is she hiding sorrow behind that smile? The orchestration is soft yet stirring, complementing the emotional gravity of the lyrics. This track reveals the depth of Cole’s interpretive talent, as he brings a quiet sadness and intrigue to each word. “Mona Lisa” became a massive hit, winning an Academy Award for Best Original Song and cementing itself as a timeless standard. It resonates not just as a love song, but as a reflection on how beauty and mystery often go hand in hand. With its rich emotional texture and cinematic quality, “Mona Lisa” remains one of Cole’s most beloved performances and a shining example of his unmatched ability to evoke feeling through music.
7. Straighten Up and Fly Right (1944)
“Straighten Up and Fly Right” marked a major breakthrough for Nat King Cole, not just as a jazz pianist but as a charismatic bandleader and vocalist. Based on a Southern folk tale that Cole’s father, a preacher, often told in sermons, the song cleverly tells the story of a monkey and a buzzard to offer a moral lesson about staying on the right path. Its swing-infused rhythm, sharp lyrics, and breezy arrangement make it both catchy and meaningful. Cole’s delivery is brimming with confidence and wit, showing his skill not only as a musician but as a storyteller. With a strong beat and a jumpin’ groove, the track was a favorite among both jazz fans and mainstream audiences, crossing racial and genre boundaries in an era still heavily divided. It also became a big hit on the charts, helping to establish Cole as a leading figure in the emerging world of popular music. The song endures because it’s more than just fun—it’s got heart and wisdom, making it a tune that still resonates today with listeners of all ages who appreciate a little swing with their life lessons.
8. When I Fall in Love (1956)
“When I Fall in Love” is a lush, romantic ballad that showcases Nat King Cole at his most tender and heartfelt. Released in 1956, the song immediately captured the hearts of listeners with its dreamy melody and timeless message. Cole’s smooth baritone floats effortlessly over a gentle orchestral arrangement, creating a mood of intimacy and longing. The lyrics speak of a love so pure and sincere that it’s only worth experiencing if it’s the real thing—unbreakable, unwavering, and forever. Cole brings emotional weight to each phrase, making listeners feel the vulnerability and hope embedded in the words. This track became a defining standard for romantic music, often used in weddings, films, and countless love stories across generations. What makes Cole’s version so special is the quiet power in his voice—a voice that doesn’t need to shout to convey depth. He brings warmth, grace, and sincerity that make this version definitive for many fans. “When I Fall in Love” is not just a song; it’s a musical vow, a soft-spoken promise of what love should be. It continues to touch hearts decades later, proving the timelessness of both the sentiment and the singer.
9. Too Young (1951)
“Too Young” captures the bittersweet nature of young love, wrapped in Nat King Cole’s deeply emotive voice and delicate phrasing. Released in 1951, this ballad was an immediate success, topping the Billboard charts for several weeks. The song tells the story of a couple in love, facing doubts from others who believe they’re too young to understand what love truly is. Yet Cole’s delivery makes it clear that the emotions are real, profound, and deeply felt—regardless of age. The tender arrangement, built around a gentle piano and lush strings, adds a sense of innocence and melancholy. Cole’s voice conveys both the defiance of young lovers and the ache of being misunderstood, making the track relatable across generations. What sets “Too Young” apart is its sincerity. There’s no flashy vocal showmanship here, just heartfelt expression that connects deeply with listeners. It struck a chord with a post-war audience seeking comfort and understanding and continues to resonate with anyone who has ever felt underestimated in love. The song remains one of Cole’s most beloved recordings and a touching reminder that love, no matter how young or old, is always real.
10. Orange Colored Sky (1950)
“Orange Colored Sky” is a joyful, jazzy burst of musical sunshine that captures the excitement of falling in love out of nowhere. Released in 1950, the song pairs a whimsical storyline with an upbeat swing rhythm, making it one of Nat King Cole’s most playful and energetic tracks. The lyrics describe a man who’s going about his day when, out of the blue, love strikes like lightning—complete with a “flash, bam, alakazam!” Cole’s delivery is charismatic and full of charm, bringing a theatrical flair to the tale. Backed by a tight, brassy arrangement, the track brims with personality and swing-era flair. It’s a song that demands attention, instantly lifting spirits with its infectious energy. Cole’s background as a jazz pianist shines through in the rhythm and phrasing, giving the tune a vibrant pulse. “Orange Colored Sky” showcases a lighter side of Cole, proving that he could swing just as effortlessly as he could croon. It remains a favorite for its fun storytelling, bright orchestration, and the sense of wonder it captures when love appears in life like magic. It’s the kind of song that makes you smile the whole way through.
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.
