Nat King Cole, the velvet-voiced crooner who defined an era, remains one of the most beloved and influential artists in music history. Whether you’re a lifelong fan or a newcomer to his timeless sound, Nat King Cole’s music is like an intimate conversation with your soul—smooth, heartfelt, and unforgettable. With his signature blend of jazz, pop, and romantic balladry, he captured hearts across the globe and left a legacy that continues to inspire artists today.
This article celebrates the very best of Nat King Cole by diving into the top 10 most popular songs that made him a legend. From chart-topping hits to his most cherished ballads, these tracks showcase the incredible artistry and emotional depth that made Cole a household name. Prepare to relive the magic of his warm, honeyed tones, his impeccable phrasing, and the timeless melodies that have soundtracked countless love stories, celebrations, and quiet moments of reflection.
So, grab a cup of coffee, settle in, and let’s journey through the unforgettable melodies and heartfelt lyrics that have cemented Nat King Cole’s place as one of the greatest voices of all time. These songs aren’t just music—they’re moments frozen in time. Let’s begin!
1. Unforgettable (1951)
Few songs capture the essence of romance and nostalgia quite like Unforgettable. Released in 1951, this Irving Gordon-penned masterpiece became one of Nat King Cole’s defining hits. His smooth, velvety vocals glide effortlessly over the lush orchestration, creating a dreamy, heartfelt ballad that has stood the test of time.
At its core, Unforgettable is a love song about the lasting impact someone can have on your heart. The lyrics paint a picture of a love so deep and profound that it lingers in memory, untouched by time. Cole’s warm, expressive delivery makes every word feel deeply personal, as if he’s singing directly to the listener. His ability to convey emotion with such subtlety and grace is part of what makes this track so enduring.
Decades after its release, Unforgettable found new life when Cole’s daughter, Natalie Cole, recorded a stunning duet version with his original vocals in 1991. This posthumous collaboration introduced the song to a new generation, earning widespread acclaim and multiple Grammy Awards.
Whether it’s played at weddings, anniversaries, or quiet, reflective moments, Unforgettable remains a timeless testament to love’s lasting power. Its elegance, sincerity, and unmatched beauty ensure that it will always hold a special place in the hearts of listeners around the world.
2. Mona Lisa (1950)
A song shrouded in mystery and romance, Mona Lisa is one of Nat King Cole’s most hauntingly beautiful ballads. Written by Ray Evans and Jay Livingston, the song was released in 1950 and quickly became a cultural phenomenon, winning the Academy Award for Best Original Song after being featured in the film Captain Carey, U.S.A..
From the moment the song begins, Cole’s voice carries a sense of wistful longing, as he croons about the enigmatic woman immortalized in Leonardo da Vinci’s famous painting. The lyrics compare the subject’s timeless beauty to the kind of love that remains just out of reach—captivating yet unattainable. This poetic theme, combined with the song’s gentle melody and sweeping orchestration, makes for an unforgettable listening experience.
Cole’s performance of Mona Lisa is a masterclass in vocal artistry. His rich, velvety tone and impeccable phrasing give the song an almost hypnotic quality, drawing listeners into its world of romance and mystery. The track’s success helped cement Cole’s reputation as one of the greatest vocalists of his time.
Over the years, Mona Lisa has been covered by countless artists, but none have matched the delicate charm and effortless grace of Cole’s original recording. It remains a timeless standard, evoking a sense of wonder and admiration just like the famous painting it was inspired by.
3. Nature Boy (1948)
A song that feels almost otherworldly, Nature Boy is one of Nat King Cole’s most profound and poetic recordings. Released in 1948, the song was written by eden ahbez, a mysterious figure known for his unconventional lifestyle and deep philosophical beliefs. From its ethereal melody to its introspective lyrics, Nature Boy is unlike anything else in Cole’s catalog.
The song tells the story of a wandering, enigmatic young man who imparts a single, powerful truth: “The greatest thing you’ll ever learn is just to love and be loved in return.” This simple yet profound message, combined with Cole’s deeply emotive delivery, makes the song feel almost like a parable—timeless and universal.
Musically, Nature Boy is delicate and haunting. The orchestration, featuring sweeping strings and a dreamy, almost hypnotic arrangement, perfectly complements Cole’s soft, expressive vocals. His ability to bring depth and sincerity to every note elevates the song from a simple ballad to a deeply moving work of art.
Despite initial skepticism from record executives, Nature Boy became a massive hit, topping the Billboard charts for eight weeks. It resonated deeply with audiences, cementing itself as one of Cole’s most beloved recordings. Even decades later, its message of love and wisdom continues to inspire listeners, proving that true artistry transcends time.
4. The Christmas Song (Chestnuts Roasting on an Open Fire) (1946)
Few holiday songs capture the warmth and nostalgia of the Christmas season quite like The Christmas Song. First recorded by Nat King Cole in 1946, this timeless classic was written by Mel Tormé and Bob Wells during a sweltering summer as an attempt to conjure images of winter’s chill. Little did they know that their song would become one of the most enduring and beloved Christmas tunes of all time.
Cole’s smooth, rich vocals and the song’s cozy, picturesque lyrics transport listeners to a scene filled with crackling fireplaces, falling snow, and children eagerly awaiting Santa Claus. The famous opening line—”Chestnuts roasting on an open fire”—immediately sets a warm and inviting tone, while the gentle orchestration wraps around the melody like a soft holiday embrace.
Although Cole originally recorded the song in 1946, he revisited it in 1953 and again in 1961 with a lush new arrangement featuring a full orchestra. This final version is widely regarded as the definitive rendition, becoming a staple of holiday music worldwide.
Each year, as Christmas approaches, The Christmas Song re-emerges as a comforting reminder of the season’s magic. It’s a song that feels like home, bringing together generations with its timeless charm and Cole’s unforgettable voice.
5. Too Young (1951)
Released in 1951, Too Young became one of Nat King Cole’s biggest hits, topping the charts for five weeks and cementing his place as a master of romantic balladry. Written by Sidney Lippman and Sylvia Dee, the song tells a heartfelt story about young love and the doubts that often accompany it.
With its tender lyrics, Too Young speaks to the skepticism young couples face from those who believe they are not mature enough to understand love. But rather than being a song of despair, it carries an air of quiet defiance, as if insisting that love knows no age. Cole’s delivery is filled with sincerity, making every word sound deeply personal and heartfelt.
Musically, the song is a perfect blend of elegance and simplicity. The delicate piano introduction and sweeping orchestration create an intimate setting for Cole’s velvety voice to shine. His effortless phrasing and emotional depth bring out the song’s beauty, turning it into an unforgettable listening experience.
Even decades later, Too Young remains a poignant anthem for anyone who has ever felt their love dismissed as fleeting or naive. Cole’s timeless performance ensures that the song continues to resonate with listeners of all ages.
6. Smile (1954)
Few songs carry as much emotional weight as Smile. Originally composed by Charlie Chaplin for his 1936 film Modern Times, the melody was later given lyrics by John Turner and Geoffrey Parsons in 1954. Nat King Cole’s heartfelt rendition remains the most well-known and beloved version of the song.
The lyrics of Smile offer a message of hope and resilience, encouraging listeners to push through difficult times with a brave face. “Smile, though your heart is aching / Smile, even though it’s breaking”—these opening lines capture the bittersweet essence of the song, acknowledging pain while offering gentle reassurance.
Cole’s delivery is nothing short of magical. His voice, warm and soothing, transforms the song from a simple tune into an anthem of quiet strength. He doesn’t just sing the lyrics; he embodies them, making every word feel like a comforting embrace. The soft, flowing orchestration adds to the song’s tender, uplifting nature.
Over the years, Smile has been covered by many artists, but none have captured its spirit quite like Nat King Cole. His version remains the definitive one, a testament to his ability to convey deep emotion with effortless grace. Whenever life feels overwhelming, Smile serves as a gentle reminder that brighter days are ahead.
7. Route 66 (1946)
Get your kicks on Route 66! With these iconic words, Nat King Cole turned an American highway into a legendary piece of musical history. Written by Bobby Troup in 1946, Route 66 is a lively and upbeat ode to the famous road stretching from Chicago to Los Angeles, capturing the excitement of travel and adventure.
Cole’s version of the song, recorded with the King Cole Trio, is a masterclass in swing and jazz. The infectious rhythm, playful piano lines, and tight harmonies create an irresistible groove, making it impossible to sit still while listening. Cole’s smooth yet rhythmic vocal delivery adds to the song’s charm, painting a vivid picture of a cross-country road trip filled with excitement and possibility.
One of the most fascinating aspects of Route 66 is how it transcends music—it has become a cultural symbol of freedom and exploration. Over the years, countless artists, from Chuck Berry to The Rolling Stones, have covered the song, but Cole’s original remains unmatched in its effortless coolness.
Even today, whether you’re actually driving down Route 66 or just dreaming of the open road, this song captures the thrill of the journey like no other. It’s a true American classic, made all the more legendary by Nat King Cole’s impeccable performance.
8. L-O-V-E (1964)
Few songs encapsulate the feeling of romance and joy as effortlessly as L-O-V-E. Released in 1964, this upbeat jazz-pop tune became one of Nat King Cole’s most enduring hits. Written by Bert Kaempfert and Milt Gabler, the song has a simple yet charming structure, spelling out L-O-V-E letter by letter in a playful, poetic manner.
Cole’s charismatic vocal delivery turns what could have been a straightforward love song into something truly special. His smooth phrasing and warm tone bring out the song’s whimsical nature, making it feel as if he’s serenading the listener directly. The arrangement, featuring a swinging big-band sound, complements his vocals perfectly. The lively horns and crisp percussion create an infectious rhythm that’s impossible not to sway along to.
Although L-O-V-E was released near the end of Cole’s career, it quickly became one of his signature songs. Over the years, it has been covered by countless artists, from Michael Bublé to Joss Stone, yet Cole’s rendition remains the gold standard. The song’s enduring popularity is evident in its frequent use in films, commercials, and wedding playlists, keeping its legacy alive for new generations to enjoy.
Whether you’re falling in love or just need a song to brighten your day, L-O-V-E is a timeless classic that never fails to bring a smile.
9. Straighten Up and Fly Right (1943)
A lively, jazz-infused tune with a moral lesson, Straighten Up and Fly Right was released in 1943 and became one of Nat King Cole’s first major hits. Co-written by Cole and Irving Mills, the song was inspired by a folk tale Cole’s father, a Baptist minister, used in his sermons. The story—about a buzzard trying to trick a naive little monkey—translates into a clever metaphor about staying on the right path in life.
With its swinging rhythm and infectious energy, Straighten Up and Fly Right perfectly showcases Cole’s jazz roots. His nimble piano work and effortless vocals glide over the upbeat melody, making it an instant classic in the swing era. The lyrics, while playful, carry a deeper meaning about integrity and resilience. Lines like “Ain’t no use in divin’ / What’s the use of jivin’?” encourage listeners to be honest and upright.
The song’s fresh and innovative sound helped propel Nat King Cole to stardom, setting the stage for his transition from jazz trio leader to mainstream pop icon. Even today, Straighten Up and Fly Right remains a staple in jazz and big-band music, proving that great storytelling and great music never go out of style.
10. When I Fall in Love (1956)
Few love songs are as timeless and heartfelt as When I Fall in Love. Released in 1956, this romantic ballad was written by Victor Young and Edward Heyman and has since become one of the most beloved love songs in history. Nat King Cole’s interpretation is widely considered the definitive version, thanks to his rich, expressive vocals and the song’s lush orchestral arrangement.
From the very first note, When I Fall in Love captures the deep yearning and vulnerability that come with opening one’s heart. Cole’s delivery is filled with sincerity and warmth, making the lyrics feel deeply personal. Lines like “When I give my heart, it will be completely” speak to a desire for true, unwavering love, resonating with listeners across generations.
The song’s orchestration, with its gentle strings and delicate piano, creates a dreamy, intimate atmosphere. It’s the kind of melody that lingers in the air long after the song has ended, leaving an emotional imprint on the listener.
Over the years, When I Fall in Love has been covered by countless artists, from Doris Day to Céline Dion, yet Nat King Cole’s version remains unmatched in its elegance and emotional depth. It’s a song that transcends time, reminding us of the beauty of love in its purest form.
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.
