Frank Sinatra, the iconic crooner and legendary voice of the 20th century, left an indelible mark on the music industry with his unparalleled talent and timeless charm. His smooth vocals, impeccable phrasing, and magnetic stage presence earned him the title of “The Chairman of the Board” and solidified his status as one of the greatest entertainers of all time. Throughout his illustrious career, Sinatra released countless hits that have become classics, resonating with audiences across generations. In this article, we delve into the captivating world of Sinatra’s discography to uncover the top 10 best songs that have stood the test of time. From heart-wrenching ballads to swinging jazz tunes, each selection showcases Sinatra’s unique ability to effortlessly captivate listeners and transport them to a different era. As we explore these exceptional compositions, we’ll celebrate the profound impact Sinatra’s music has had on popular culture and recognize the unmatched artistry of a true music legend. So sit back, relax, and prepare to embark on a musical journey through the very best of Frank Sinatra’s incomparable repertoire.
1. “That’s Life”
This legendary tune “That’s Life” by Frank Sinatra showcases his signature style of crooning and swing. The song's lyrics convey an optimistic attitude towards life despite setbacks.
Sinatra's musicality adds flair to the composition by embracing the brass section, creating a unique sound.
It reached #4 on the Billboard charts in 1966 and has remained beloved through the years.
A lesser-known fact is that Sinatra was displeased with his vocal take, but his producer convinced him to release it anyway.
Move over, Statue of Liberty, 'New York, New York' is the true symbol of the Big Apple.
2. “New York, New York”
This track, capturing the essence of New York's fast-paced energy, has become an anthem for the city. Sinatra's lively delivery along with Kander and Ebb's catchy tune creates a festive atmosphere that makes it an all-time classic. It debuted in 1977 and has since been used in numerous films and advertisements. While the song continuously conjures images of grandeur and glamour for its subject matter, it also exudes grittiness and determination that personify its spirit.
A driving percussion beat sets the perfect tone for the lyrics as Sinatra sings about making it big in the Big Apple: "If I can make it there, I'll make it anywhere." The soaring chorus, with its infectious melody and unabashed optimism, underscores his conviction to conquer New York City. This combination of powerhouse vocals, unconventional phrasing, and irresistible hooks has made "New York, New York" one of Sinatra's most unforgettable hits.
Despite not being an immediate hit upon release, "New York, New York" quickly became synonymous with Frank Sinatra – and rightfully so. Even renowned singer Liza Minnelli covered this iconic song but could not steal away its charm-making Sinatra's version undeniably timeless.
It is remarkable that "New York, New York" was actually not written for Frank Sinatra at all but was originally composed for Liza Minnelli's 1977 film "New York," "New York." However, once Ol' Blue Eyes recorded his own take on the tune as the title track of his 1980 album "Trilogy: Past Present Future," there was no taking it back – the rest is history!
Sinatra's voice on 'Fly Me To The Moon' is like a warm blanket on a cold night, except it's a blanket made of whiskey and cigarettes.
3. “Fly Me To The Moon”
This classic Sinatra track, first recorded in 1964, is considered one of his signature songs. “Fly Me To The Moon”, also known as “In Other Words”, was written by Bart Howard in 1954 and has been covered numerous times since. With its romantic lyrics and timeless melody, the song remains a favorite among Sinatra fans and jazz enthusiasts alike.
In his smooth, silky voice, Sinatra sings about wanting to escape with his lover to the moon and stars above. The song’s catchy chorus features the memorable lines: “Fly me to the moon / Let me play among the stars / Let me see what spring is like /On a-Jupiter and Mars”.
Interestingly, despite its popularity, “Fly Me To The Moon” was never a major hit when it was first released. It wasn’t until years later that the song became widely recognized and beloved among music lovers.
Legend has it that Sinatra’s fascination with space travel inspired him to choose this song as part of his repertoire. In fact, in 1965 he even attended a gala event at NASA’s Houston Space Center where he performed this classic tune for astronauts.
Overall, “Fly Me To The Moon” is a timeless piece of music that continues to enchant listeners decades after it was first recorded by Frank Sinatra. Sinatra's love song about strangers in the night might sound romantic, but let's be real, it's a little creepy if you actually meet someone in a dark alley.
4. “Strangers In The Night”
This iconic tune by Frank Sinatra is well-known for its memorable opening melody, suave vocals and top-notch instrumentation. Its sophisticated harmonic structure, combined with the swinging brass section and Sinatra's effortless delivery, make it a classic example of big band jazz. The song tells a tale of two strangers who meet one night and share a romantic moment together. "Strangers In The Night" has stood the test of time as a beloved favourite among listeners worldwide. Its popularity continues to captivate music lovers of all generations.
Frank didn't just sing 'My Way', he owned it with the same confidence as a cat walking away from an explosion in slow motion.
5. “My Way”
This classic tune, often referred to affectionately as “The Sinatra Anthem,” continues to resonate with audiences around the world. The timeless lyrics and iconic melody of this song have made it a beloved favorite for generations. Sinatra’s spirited delivery brings an unmatched level of emotional depth to the powerful lyrics, making this tune an instant classic.
“My Way” is a soaring masterpiece that showcases not only Sinatra’s vocal prowess but also his impeccable taste in music. Subtle orchestration combines with strong percussion and guitar lines to create the perfect environment for Sinatra’s emotive performance. From the opening notes to the final chorus, this song never fails to captivate its listeners.
It’s interesting to note that despite being one of his most successful recordings ever, “My Way” was initially met with some resistance from both critics and fans alike. However, over time it became clear that this song possessed a special quality that truly set it apart from anything else at the time. In fact, it remains one of Sinatra’s most recognizable songs today and serves as a shining example of his accomplishments as both an artist and an entertainer.
Frank may have had them under his skin, but his music is sure to get under yours with this timeless classic.
6. “I’ve Got You Under My Skin”
This classic tune is a gem in Frank Sinatra's collection. The smooth and soothing vocals of the legend paired with the powerful lyrics make it one of his best. The song was released in 1956, and it instantly became a hit.
“I’ve Got You Under My Skin” is known for its beautiful melody and the heartfelt emotions it evokes in listeners. It showcases Sinatra's impeccable voice range, as well as his ability to deliver a powerful performance with every note he sings.
Interestingly, this song was written by Cole Porter for the film "Born to Dance" but became famous after Sinatra popularized it. Its popularity keeps growing even today, long after Frank's passing.
Pro Tip: Listen to the song while paying close attention to the lyrics to truly appreciate its beauty and impact on music history.
Sinatra's voice is like a fine wine, and 'The Way You Look Tonight' is the vintage we all want to sip on.
7. “The Way You Look Tonight”
This timeless classic crooned by Sinatra has stood the test of time and remains an all-time favorite.
Sinatra skillfully delivers the lyrics with his smooth voice, which enhances the melody and elevates the song to new heights. Its popularity is linked to its presence in iconic films and TV shows, further cementing its place in pop culture history.
Interestingly, "The Way You Look Tonight" was originally written for the 1936 film Swing Time and won an Academy Award for Best Original Song that year. With such historic significance, it is no surprise this track remains a fan favorite decades later.
Sinatra sings the perfect soundtrack for sipping a cold drink on a warm summer day with 'Summer Wind'.
8. “Summer Wind”
This classic song, often associated with the summer season, captures the essence of Sinatra's smooth vocals and unmatched charisma. With its charming lyrics and upbeat melody, “Summer Wind” effortlessly transports listeners to a serene and carefree place. Its popularity has persisted throughout generations, making it one of the best-loved tracks from Sinatra's extensive repertoire. It's hard not to fall in love with this classic tune, which is a testament to Sinatra's enduring legacy as an icon of American music.
Sinatra's impeccable timing and effortless command of the lyrics make “Summer Wind” an enduring favorite for many fans. Its catchy melody and romantic themes have made it an instant classic, cementing its place as one of the most beloved songs in his repertoire.
Interestingly enough, “Summer Wind” was not originally written for Sinatra but was covered by him later in life after it had already become popular. Despite its unconventional origins, the song has come to be closely associated with Sinatra and is a staple on almost every list of his greatest hits.
"Summer Wind" truly embodies the essence of Frank Sinatra – timeless, elegant, and irresistibly cool. With its crisp horns and lush orchestrations backing up Frank's iconic voice, it is no surprise that this song has become such a fan favorite. If you haven't yet experienced the magic of "Summer Wind," you're missing out on one of the greatest songs ever recorded.
Frank had the world on a string, but I struggle to keep my keys in my pocket.
9. “I’ve Got The World On A String”
This timeless classic from Frank Sinatra, arguably one of the most popular songs in his vast repertoire, exudes confidence and a sense of triumph. The song, unofficially considered an anthem for those who have achieved success against all odds, features an upbeat tempo complemented by powerful lyrics and melodious vocals.
As Sinatra sings "I've got the world on a string, sittin' on a rainbow," he conveys a sense of accomplishment and celebrates life's successes. The song's message is empowering – it reminds us that anything is possible if we remain optimistic and keep striving towards our goals.
Notably, the optimism and confidence in "I've Got the World on a String" are further emphasized by the inclusion of horn arrangements which orchestrate the triumphant chorus. The overall effect is an uplifting song that leaves listeners feeling inspired and motivated.
Pro Tip: If you're ever feeling discouraged or overwhelmed, listen to this classic Sinatra hit for an instant boost of positive energy.
Sinatra clearly had better luck in his kind of town than I do in mine.
10. “My Kind Of Town”
This track exemplifies Sinatra's love for his hometown. He identifies Chicago as his 'kind of town', with lyrics that paint a picture of the bustling streets and lively culture. The bouncy piano intro is instantly recognizable, and the energetic horns will guide even the most reserved listener into singing along with the catchy chorus. This song perfectly encapsulates Sinatra's nostalgic pride for his upbringing in Chicago, and it continues to be a fan favorite.
A testament to Sinatra's lifelong love of Chicago. The lyrics conjure up images of bustling city streets and its colorful culture while its opening notes on piano are famous. With an energetic chorus, it holds a special place in many hearts.
Fans often recount endearing memories with this song playing during their childhood or at family gatherings.
Samuel Moore 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.
