The 10 best Nat King Cole songs of all time

Nat King Cole (1919-1965) was a legendary American jazz pianist and singer celebrated for his smooth, velvety voice and impeccable phrasing. Born Nathaniel Adams Coles in Montgomery, Alabama, he began his career as a jazz pianist before finding fame as a singer. Cole’s distinctive baritone voice became his trademark, and he achieved great success with hits such as “Unforgettable,” “Mona Lisa,” and “The Christmas Song (Chestnuts Roasting on an Open Fire).” He broke racial barriers in the entertainment industry and became the first African American to host a nationally televised variety show, “The Nat King Cole Show,” in the 1950s. Nat King Cole’s legacy continues to influence jazz and popular music to this day.

1. Stand upright and fly properly

“Straighten Up and Fly Right” is a classic song by Nat King Cole, originally recorded in 1943. Written by Nat King Cole himself along with Irving Mills, the song has a catchy melody and witty lyrics inspired by a folk tale Cole’s father used to tell him. The lyrics advise “the monkey” (representing mischievous behavior) to straighten up and “fly right” (behave properly). The song became a huge hit for Cole and is considered one of his best known songs, showcasing his smooth vocals and charming delivery. “Straighten Up and Fly Right” remains a timeless example of Nat King Cole’s enduring talent and charm.

2. When I fall in love

“When I Fall in Love” is a classic ballad originally recorded by Nat King Cole in 1956. It features Cole’s smooth and velvety vocals accompanied by lush orchestration. The song’s lyrics express the romantic feelings and emotions experienced when falling in love. “When I Fall in Love” became one of Nat King Cole’s signature songs and remains a timeless classic in the repertoire of jazz and pop standards. It has been covered by numerous artists over the years, cementing its status as a popular and enduring love song.

3. Stardust

“Stardust” is a jazz standard originally composed by Hoagy Carmichael, with lyrics by Mitchell Parish. The song was first recorded in 1927 and has since become one of the most recorded songs of the 20th century, with interpretations spanning multiple genres. Nat King Cole’s rendition of “Stardust” is particularly notable for its lush orchestration and smooth, velvety vocals. The song’s lyrics evoke a nostalgic and dreamy atmosphere, reflecting memories and romantic yearnings. Cole’s rendition, recorded in 1957, remains one of the definitive versions of “Stardust,” and showcases his mastery of phrasing and emotional delivery.

4. Unforgettable

“Unforgettable” is a timeless classic originally sung by Nat King Cole and released in 1951. It features Cole’s rich, velvety vocals accompanied by a lush orchestral arrangement. The song’s lyrics express the unforgettable nature of a romantic relationship and the enduring love between two people. “Unforgettable” became one of Nat King Cole’s most iconic songs and continues to resonate with audiences for its heartfelt sentiment and beautiful melody. The song has since been covered by various artists, including a memorable duet version with his daughter Natalie Cole, released posthumously in 1991.

5. Mona Lisa

“Mona Lisa” is a classic song by Nat King Cole, released in 1950. It features Cole’s smooth vocals accompanied by a soft orchestral arrangement. The lyrics describe the mysterious and enigmatic smile of the famous painting by Leonardo da Vinci, comparing it to the smile of a charming woman named Mona Lisa. “Mona Lisa” became one of Nat King Cole’s best known songs and a huge hit, winning the Academy Award for Best Original Song in 1950. It remains a timeless classic, known for its romantic lyrics and Cole’s soulful performance.

6. Country Boy

“Nature Boy” is a song written by Eden Ahbez in 1947. The song’s melody and lyrics convey a mystical and ethereal quality, reflecting Ahbez’s naturalistic and spiritual beliefs. Nat King Cole’s 1948 recording of “Nature Boy” became a major hit, reaching the top of the charts and cementing his reputation as a versatile and expressive singer. The song’s message of the wisdom of living in harmony with nature and striving for love and understanding resonated with audiences, and it has since been covered by numerous artists across multiple genres. “Nature Boy” remains a timeless classic, celebrated for its evocative lyrics and haunting melody.

7. Too young

“Too Young” is a song originally sung by Nat King Cole and released in 1951. It is a romantic ballad that explores the innocence and transience of youth. The lyrics describe a love that is considered too young and tender to last, but is nevertheless full of real feelings and longing. Nat King Cole’s soft and soulful vocals, combined with a gentle orchestral arrangement, convey the poignant mood of the song. “Too Young” became a major hit for Cole, topping the charts in the United States and earning him widespread acclaim for his vocal performance and interpretation of the song’s lyrical depth.

8. Smile

“Smile” by Nat King Cole is a poignant rendition of the classic song originally composed by Charlie Chaplin. Released in 1954, Nat King Cole’s version of “Smile” is celebrated for its heartfelt performance and soulful interpretation. The lyrics, which encourage finding strength and positivity even in difficult times, resonate with listeners. Cole’s smooth and velvety voice perfectly captures the essence of the song, making it one of his most iconic performances. “Smile” has since become a timeless standard, treasured for its beauty and timeless message of resilience.

9. Pretend

“Pretend” is a classic pop song originally recorded by Nat King Cole in 1953. It features Cole’s warm and smooth vocals accompanied by a light orchestral arrangement. The lyrics of “Pretend” convey a sense of longing and fantasy, urging the listener to pretend that a lost love has returned. The song’s gentle melody and nostalgic theme resonated with audiences, making it a popular hit in its time. Nat King Cole’s gentle delivery and emotional interpretation added to the enduring charm of “Pretend” and cemented its place as a beloved classic in his repertoire.

10. LOVE

“LOVE” is a popular jazz standard originally recorded by Nat King Cole in 1965. The song features Cole’s signature smooth vocals accompanied by a lively and upbeat arrangement. “LOVE” is known for its catchy melody and playful lyrics that spell out the word “love” and emphasize the joy and excitement of romance. The song became a huge hit for Nat King Cole and showcased his charm and charisma as a singer. “LOVE” has since been covered by numerous artists and remains a timeless classic celebrated for its infectious positivity and feel-good vibes.

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