The 10 best Nat King Cole songs of all time

Nat King Cole, born Nathaniel Adams Coles, was an American singer and jazz pianist who became one of the most popular and influential entertainers of the 20th century. He was born on March 17, 1919, in Montgomery, Alabama, and grew up in Chicago, Illinois. Cole first rose to prominence as a jazz pianist, but his greatest success came as a singer, known for his smooth baritone voice and impeccable phrasing.

Cole’s career spanned three decades and he recorded numerous hits in various genres, including jazz, pop and R&B. His best known songs include “Unforgettable,” “The Christmas Song (Chestnuts Roasting on an Open Fire),” “Mona Lisa” and “Nature Boy.”

Cole was also a trailblazer for African-American artists, breaking racial barriers in the music industry. He was the first African-American to host a nationally televised variety show: “The Nat King Cole Show,” which aired in the late 1950s.

Nat King Cole’s music continues to be celebrated for its timeless quality and his lasting influence on popular music. He died on February 15, 1965, but his legacy as a legendary musician lives on.

1. Stand upright and fly properly

“Straighten Up and Fly Right” is a popular song written by Nat King Cole and Irving Mills in 1943. It was first recorded by the King Cole Trio (Nat King Cole’s group) and became one of their early hits. The song is known for its catchy melody and clever lyrics, which tell the story of a monkey who outwits a buzzard by telling it to “straighten up and fly right.”

The song’s title and lyrics are based on a folk tale that Cole’s father, a Baptist minister, used to tell him. The song’s message is encouraging and wise, urging listeners to stay on the right path and not be deterred by temptation or adversity.

“Straighten Up and Fly Right” was a commercial success for Nat King Cole and helped him become a leading figure in popular music. The song has since been covered by numerous artists and remains a classic of the jazz and pop genres.

2. When I fall in love

“When I Fall in Love” is a classic pop standard originally written in 1952 by Victor Young (music) and Edward Heyman (lyrics). The song has been covered by many artists, but one of the most famous versions is by Nat King Cole. Cole’s rendition, recorded in 1956, is particularly noted for its lush orchestration and Cole’s smooth, velvety vocals.

The song is a ballad that expresses the feeling of being in love and the depth of emotion that comes with it. The lyrics describe the beauty and wonder of love and capture the romantic essence of the feeling. “When I Fall in Love” has become a timeless classic, loved for its soulful lyrics and beautiful melody. It remains one of Nat King Cole’s most popular songs and showcases his talent as a singer and his ability to convey deep emotions through music.

3. Stardust

“Stardust” is a popular song composed by Hoagy Carmichael in 1927, with lyrics added by Mitchell Parish in 1929. It has been recorded by countless artists over the years and has become one of the most recorded songs of the 20th century. The melody of the song is cheerful and evocative, while the lyrics describe a nostalgic longing for love and the past.

Nat King Cole recorded a version of “Stardust” in 1957 that is widely considered to be one of the definitive interpretations of the song. Cole’s smooth and velvety voice perfectly captures the wistful and romantic mood of the song, making it one of his most popular recordings.

“Stardust” has now become a jazz standard, appreciated for its timeless melody and poignant lyrics. It has been covered by artists from a variety of genres and continues to enchant listeners with its dreamy and ethereal quality.

4. Unforgettable

“Unforgettable” is a popular song written by Irving Gordon and first recorded by Nat King Cole in 1951. The song’s lyrics describe the feeling of being in love and how the memories of a loved one live on. Nat King Cole’s smooth, velvety voice and the song’s lush orchestration helped make it a timeless classic.

In 1991, Natalie Cole, daughter of Nat King Cole, recorded a duet version of “Unforgettable,” incorporating her father’s original vocals from his 1951 recording. The duet was a posthumous collaboration made possible by technology, and became a huge success, winning several Grammy Awards, including Record of the Year and Song of the Year.

Often associated with Nat King Cole, “Unforgettable” is considered one of his most famous songs. Natalie Cole’s duet version breathed new life into the song and introduced it to a new generation of listeners, ensuring its lasting legacy.

5. Mona Lisa

“Mona Lisa” is a popular song by Ray Evans and Jay Livingston. It was originally recorded by Nat King Cole in 1950 and became one of his signature songs. The song is a tribute to the famous painting by Leonardo da Vinci and describes the charm and mystery of the Mona Lisa’s smile.

Nat King Cole’s soft and soulful vocals, combined with the song’s romantic lyrics and lush orchestration, made “Mona Lisa” a timeless classic. The song became a huge hit, reaching the top of the charts and winning the Academy Award for Best Original Song in 1950.

Over the years, “Mona Lisa” has been covered by many artists and continues to be a popular choice for performers, but Nat King Cole’s version remains the most iconic and is considered one of the greatest songs of the 20th century.

6. Country Boy

“Nature Boy” is a song written by Eden Ahbez in 1947. The song tells the story of a “strange, enchanted boy” who wanders through life, experiencing its joys and sorrows with a deep sense of wisdom and wonder. The lyrics reflect themes of love, nature and spirituality, with the “Nature Boy” conveying his philosophy of living in harmony with the world.

Nat King Cole’s recording of “Nature Boy,” released in 1948, became a huge hit and is considered one of his best-known songs. Cole’s warm, smooth voice and the song’s haunting melody combine to create a timeless classic that resonated with listeners.

“Nature Boy” has since been covered by numerous artists and has become a jazz standard. Its enduring popularity is a testament to the song’s universal message of love and acceptance, as well as its striking melody and lyrics.

7. Too young

“Too Young” is a song written by Sidney Lippman and Sylvia Dee and made popular by Nat King Cole. It was first recorded by Nat King Cole in 1951 and became one of his early signature songs.

“Too Young” is a romantic ballad that describes the feelings of falling in love at a young age. The lyrics of the song convey a sense of innocence and nostalgia, reflecting on the transience of youth and love. Nat King Cole’s smooth and velvety voice, coupled with the song’s gentle melody and lush orchestration, have helped make it a timeless classic.

“Too Young” was a huge hit for Nat King Cole, reaching the top of the charts and earning him his first gold record. The song remains one of his most popular recordings and is often considered one of the greatest love songs of all time.

8. Smile

“Smile” is a song originally composed by Charlie Chaplin for the soundtrack of his 1936 film Modern Times. The music was later set to lyrics by John Turner and Geoffrey Parsons and recorded by many artists, including Nat King Cole.

Nat King Cole’s version of “Smile”, recorded in 1954, is perhaps the most famous and enduring interpretation of the song. Cole’s warm and soothing voice, combined with the song’s uplifting message, struck a chord with listeners and cemented the song’s status as a classic.

“Smile” is a poignant and hopeful song that encourages listeners to keep smiling even in the face of adversity. Its timeless message of resilience and optimism has made it a favorite of many generations, and it remains one of Nat King Cole’s most popular recordings.

9. Pretend

“Pretend” is a popular song written by Lew Douglas, Cliff Parman and Frank Levere. It was first recorded by Nat King Cole in 1953 and became one of his classic hits.

“Pretend” is a love song that tells the story of a person who pretends that their love is reciprocated, even though they know it is not. The lyrics of the song convey a sense of longing and desire as the protagonist imagines a world where his love is reciprocated.

Nat King Cole’s smooth and soulful vocals, combined with the song’s melodic arrangement, helped make “Pretend” a chart hit. The song remains a favorite among Nat King Cole fans and is considered one of his best-known recordings.

10. LOVE

“LOVE” is a jazz standard composed by Bert Kaempfert and Milt Gabler in 1965. The lyrics were written by Gabler and the song was originally recorded by Nat King Cole for his album of the same name.

“LOVE” is an upbeat and catchy song that pronounces the word “love” and describes the joy that love brings. The song’s upbeat melody and upbeat lyrics have made it a popular choice for weddings and other celebrations.

Nat King Cole’s recording of “LOVE” is one of his most famous songs and has remained a classic in the jazz and pop genres. His smooth vocals and the song’s catchy melody have ensured its enduring popularity and it remains a popular song to this day.

Edward Tomlin is a regular contributor to Singers Room. Since 2005, Singersroom has been the voice of R&B around the world. Connect with us on social media below.