7 Best Frank Sinatra Songs That Defined His Career, Per Fans

Frank Sinatra is widely regarded as one of the greatest vocalists of all time, with a career that spanned over six decades. His smooth voice and impeccable phrasing made him a beloved figure in the world of music, and his songs continue to be cherished by listeners of all ages to this day. This is why today, we at StudyFinds decided to delve further into the singer’s discography, finding only the best Frank Sinatra songs that have stood the test of time and continue to captivate audiences around the world. From classic ballads to swinging jazz tunes, Sinatra’s song list is a treasure trove of musical gems that showcases his immense talent and enduring appeal. So, let’s dive in and take a closer look at some of the standout tracks from Old Blue Eyes himself.

Of course, there is a lot to learn about the Chairman of the Board far beyond his songs. Born Francis Sinatra to Italian immigrants in New Jersey, Frank Sinatra’s rise to fame was nothing short of remarkable. From his humble beginnings as a singing waiter in the ’30s to becoming one of the most iconic and influential entertainers of the 20th century, Sinatra’s journey is a testament to hard work and perseverance. Whether performing solo or with his famous Rat Pack buddies, Sinatra always knew how to captivate a crowd and leave them wanting more. As always, we researched across eight expert sources to bring you the top seven best Frank Sinatra songs of all time that were mentioned most. Don’t agree with our list? No worries. We would love to hear from you in the comments below! 

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Frank Sinatra Record (Photo by Ethan Rougon on Unsplash)

The List: Best Frank Sinatra Songs That Fans Love

1. “My Way” (1969)

The first song on our list may be an obvious choice, but we have to give it to you anyway. It, of course, is “My Way.” Jazz Fuel notes this track as easily being Sinatra’s “most famous” song, and its impact on society as a whole cannot be overstated. “My Way” is truly a timeless classic that showcases Sinatra’s vocal talent and emotional depth.

Reported as being the song that “helped Frank reinvent himself” by U Discover Music, “My Way” was composed by Jacques Revaux and Gilles Thibault, with the English lyrics being lent by Paul Anka, another famous crooner. The song’s powerful lyrics about living life on one’s own terms struck a chord with audiences worldwide, making it an anthem for self-expression and individuality. Sinatra’s heartfelt delivery and impeccable phrasing elevate the song further to legendary status.

Music in Minnesota explains that this signature number was, in fact, not just a favorite among Sinatra fans but also earned him his first Grammy award. Sinatra’s performance of “My Way” at his live concerts became a highlight for fans, with many considering it to be his definitive song. Sinatra’s emotional connection to the lyrics, combined with his unparalleled vocal talent, continues to resonate with listeners of all generations, ensuring that “My Way” will always hold a special place in music history.

2. “Strangers In the Night” (1966)

The next song to grace our list is “Strangers in the Night,” and like with most Sinatra classics, he wasn’t originally intended to sing the song. He was, however, the one that made it a hit, according to Music in Minnesota. The track’s romantic lyrics and catchy melody have made it a timeless favorite among fans, making it no wonder this song continues to be a staple on any Sinatra playlist.

Magic City Smooth Jazz goes on to add that the “ad-libbed ‘doo-be-doo-be-doo'” became a signature for Sinatra, proving that it’s the unique moments that one brings to a song that makes them truly magical. Sinatra’s effortless charm and smooth vocals truly bring “Strangers in the Night” to life, leaving a lasting impression on listeners of all generations. His ability to infuse emotion and personality into every note is what sets him apart as a legendary performer.

While Live 365 notes that Sinatra himself had “nothing but bad things” to say about this ballad, “Stranger in the Night” still continues to resonate with fans of Old Blue Eyes regardless of his opinions. His disdain for the song only adds to the mystique and allure of his performance, as fans are able to appreciate the passion he brings to the lyrics despite his personal feelings. With each note and every word, Sinatra proves why he will always be remembered as an icon in the world of music.

3. “Theme From New York, New York” (1977)

The next classic to take up ranks on our list is the “Theme From New York, New York.” As Jazz Fuel explains, this song was originally written for the Scorsese film “New York, New York,” where it is performed with just as much chutzpa (if not more) by Liza Minnelli. Sinatra’s rendition of this iconic song captures the essence of the Big Apple just as much, and his smooth vocals and powerful delivery seem to bring the lyrics to life.

As Live 365 states, much of the song’s fame comes from being the go-to celebratory tune to play once the New Year’s Eve ball drops in New York City. Sinatra’s version of “Theme From New York, New York” has become synonymous with the city itself, embodying the hustle, bustle, glamor, and grit of New York. It’s no wonder that this song has stood the test of time and continues to be a beloved anthem for the city that never sleeps.

Music Grotto notes this ditty as being “one of the best songs in all of American cinema history.” Sinatra’s take managed to be his last big hit single, even earning him yet another Grammy nomination. The song’s enduring popularity is a testament to its ability to evoke the magic and energy of the city in a way that resonates with listeners of all generations. 

4. “That’s Life” (1966)

“That’s Life” is the next song to take up residence on our list, and for good reason. According to Music Grotto, the song not only peaked at number four on the “Billboard Hot 100” but also at number one on the “Easy Listening Charts.” Its timeless lyrics and catchy melody make it a favorite for listeners of all ages, and its universal message of perseverance and resilience makes it a song that will continue to resonate with listeners for years to come.

First For Women mentions the song was written by Dean Kay and Kelly Gordon, and became a staple for Sinatra in his live shows and remains one of his most iconic songs to this day. The song perfectly captures the ups and downs of life, resonating with audiences around the world. 

Singers Room adds that “That’s Life” is more than just a song; “it’s an anthem” that continues to inspire and uplift countless individuals. The powerful lyrics, combined with Sinatra’s impeccable vocals, make it a timeless masterpiece that transcends generations. The raw emotion and authenticity in his rendition of “That’s Life” make it a song that will forever hold a special place in the hearts of music lovers everywhere. 

5. “Fly Me To the Moon” (1964)

The next song on our ranking is an “undisputed classic,” according to Live 365, and we couldn’t agree more. We must be talking about “Fly Me to the Moon.” Recorded by Sinatra in 1964, this song has stood the test of time and remains a favorite among listeners of all ages. Its smooth vocals and timeless melody make it a perfect choice for any romantic occasion or just a relaxing evening at home.

“Fly Me to the Moon” is described as being “unparalleled” by Singers Room in terms of Sinatra’s vocal artistry and emotional depth. The way he effortlessly croons the lyrics, accompanied by the dreamy orchestration, transports listeners to a place of pure bliss. It’s no wonder that this song continues to be a beloved classic that will never go out of style.

Originally written in 1954, it wasn’t until the song was “given a bossa nova sound by Joe Harnell” that Sinatra took notice of it, says Music in Minnesota. This new version added a new layer of sophistication to the already timeless track, showcasing Sinatra’s ability to adapt and evolve with the changing musical landscape. Whether you’re a longtime fan of Sinatra or a newcomer to his music, “Fly Me to the Moon” is sure to captivate and enchant you with its timeless charm and undeniable beauty. 

6. “I’ve Got You Under My Skin” (1956)

The next song is Sinatra’s 1956 version of “I’ve Got You Under My Skin.” Like most tracks on this list, the song has been covered by many performers through the decades, but it was the Chairman of the Board who “made this hit song a significant success,” according to Music in Minnesota. His rendition of “I’ve Got You Under My Skin” showcases his talent for interpreting songs with depth and emotion, solidifying his status as one of the greatest singers of all time.

Magic City Smooth Jazz notes that this song was originally a Cole Porter composition, but Sinatra decided to add a “big-bad arrangement” to the track. Sinatra’s decision to enhance the song with a powerful arrangement truly elevated its impact and made it a timeless classic. Sinatra’s version of the song remains a standout in his extensive discography, showcasing his ability to take a well-known tune and make it uniquely his own.

First For Women even goes as far as to call Sinatra’s take on this song as being the “definitive” version of “I’ve Got You Under My Skin.” The way he effortlessly delivers the lyrics with passion and emotion truly sets his version apart from others, solidifying its place as a beloved standard in the world of jazz and popular music. Sinatra’s interpretation of “I’ve Got You Under My Skin” remains a shining example of his unparalleled talent and artistry.

7. “Come Fly With Me” (1958)

The last, but certainly not even close to being the least, song on today’s ranking is “Come Fly With Me.” In this track, “Sinatra invites the listener to join him on a global romantic adventure,” adds Magic City Smooth Jazz. With its upbeat tempo and smooth vocals, “Come Fly With Me” is a timeless classic that never fails to transport listeners to a place of wanderlust and romance.

The song was specifically written for Sinatra for his 1958 album of the same name by Jimmy Van Heusen and Sammy Cahn, mentions First For Women and has been featured in tons of memorable films. The song’s catchy melody and charming lyrics have made it a favorite for both fans of jazz and casual listeners alike. Sinatra’s effortless delivery and charisma shine through in this iconic track, making it a must-listen for anyone looking to add a touch of old-school glamor to their music collection.

Sinatra, having a reputation for always being “on the move,” was the perfect muse for this track, explains Music in Minnesota. The song’s timeless appeal has ensured its enduring popularity, with new generations discovering and falling in love with it all over again. Sinatra’s interpretation of the song perfectly captures the essence of the Rat Pack era, making it a standout in his extensive discography and a true classic overall.


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About the Author

Jilly Hite

Janelle is a freelance writer from New York. Her writing focuses on parenting, tech, business, interior design, education, and telling people’s inspiring stories. Janelle has written for Mustela and Newton Baby and has bylines in Pregnant Chicken, Syracuse Woman Magazine, the Baldwinsville Messenger, and Family Times Magazine. She holds a master’s degree in literacy from the State University of New York at Oswego.

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  1. I felt that his singing improved with age, overall, and agree that he expressed his emotions with greater depth as he matured. One song I love is “That’s why the lady is a tramp.” Which he did with Ella Fitzgerald, my all time favorite lady.

  2. What happened to ” The Summer Wind ” – definitely a very big favorite among his real fans.

  3. You have picked the most wonderful song of his career. I went to see Frank when his was with Dean and Liza M. The greatest show ever.

  4. I’ve seen Frank Sinatra over 15 times he was fantastic he was touring with Dean Martin some Sammy Davis and Liza Minnelli. They put on the best show you can imagine.

  5. I’m a huge Frank fan. You nailed this one on the head! I often do not agree with lists of this nature, you y’all are 100% on this.

  6. I think the Sinatra choices are very good. My personal favorites are on the album Frank did with Antonio Carlos Jobim. From Brazil his daughter Nancy ‘s favorite album.

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