11 Best Frank Sinatra Songs of All Time

frank sinatra on stage in a suit singing songs
Washington, D.C. USA, October 1st, 1992 Frank Sinatra in performance at the reopening of the Warner Theater in Washington DC. Image from Shutterstock.

Frank Sinatra has been known as one of the best and most iconic singers of big band music of all time. Ol’ Blue Eyes, as he has often been called, has been known for his crooning sound since he hit the music scene at the beginning of his career.

Although he was often known for his time on the big screen, he is most known for some of the best and most iconic songs in the music industry. Frank Sinatra, while he had a specific sound, has crossed the generational divide that shows that his music was meant to stay for years to come.

Want to know what the best Frank Sinatra songs of all time are? Keep reading to find out.

1. “My Way”

Did you know that one of his most iconic signature songs became one of his least favorites? 

Although it has been reported that Ol Blue Eyes did not like the song, “My Way” became one of his most popular songs throughout his career. When most people think of Sinatra, this is the song that they mention most often.

The song was a remake of the original version, “Comme d’Habitude’ (As Usual), which was written by Jacques Revaux, Gilles Thibault, and Claude Francois. The song was remade for English with the English lyrics written by Paul Anka.

This lonely-sounding song, with Sinatra’s legendary crooner sound, became the signature song that allowed him to showcase his unique vocal sounds and eventually earned the artist a Grammy. 

It was a song that sent the cultural message that it was okay to go against the norm and do things your way, which is stated in the chorus. The idea took off, at least for Sinatra, as it also paved his way into the Rock & Roll Hall of Fame.

Even if you are not a huge fan or well-versed in the various songs of Frank Sinatra, “My Way,” is most likely the most recognizable anthem in his repertoire. This is because, throughout his career, it became known as one of the most popular signature songs of all time.

Related: 10 Crazy Frank Sinatra Facts: His Mob Involvement, Crazy Sex Parties, and More

2. “Strangers in the Night”

Interestingly enough, when it was learned by Reprise Records that the song was offered not only to Sinatra but also to Jack Jones, they immediately got to work on the tune. This caused them to have it ready much sooner and was able to release it first.

Hitting the tops of charts like the Billboard Hot 200 for more than 15 weeks, and spending one week at the number one spot, “Strangers in the Night” is one of Sinatra’s best songs.

The song was written by Eddie Snyder and Charles Singleton and composed by Bert Kampfert for the movie “A Man Could Get Killed.”

Although the song was not written for Frank Sinatra, he is the one that made it a hit.

“Strangers in the Night” earned Sinatra quite a bit of notoriety over the years and hit the tops of several charts along the way. Even though this is true, Sinatra was not the biggest fan of the song.

3. “The Way You Look Tonight”

Known by many as one of the most romantic Frank Sinatra songs of all time, “The Way You Look Tonight” was made even more special by adding the crooning sound of the Chairman of the Board.

The words to Sinatra’s famous song were written by Dorothy Fields and composed by Jerome Kern. The song was originally performed by Fred Astaire in the movie Swing Time but was made famous by Sinatra.

The song may not have been Sinatra’s originally, however, it has been made famous with Ol’ Blue Eyes’s crooner sound. It has been one of the most popular songs at weddings and in romance movies throughout the years. It was even rated one of the best songs of all time. 

“The Way You Look Tonight” has not only been on the top of the charts for many years but has also been on some of the top playlists on websites such as the Spotify App and Apple Music. Frank Sinatra is one of the most transitional musical artists of all time who has had the power to cross the generational divide.

4. “I’ve Got You Under My Skin”

In 1936, Cole Porter wrote “I’ve Got You Under My Skin” and was introduced in the movie, Born to Dance to be performed by Eleanor Powell.

Although the song was performed by several artists throughout the years, it was Sinatra who made this hit song a significant success.

When Sinatra began performing it on his weekly radio show, it was a remixed version that he worked on with Nelson Riddle. Once Sinatra added his soulful voice to the mix, “I’ve Got You Under My Skin” became bigger than it was ever expected to be.

In 1963, Sinatra recorded the song again for his album Sinatra’s Sinatra. It was recorded once again with the addition of U2 and Bono’s signature sound on the album Duets.

Even though Sinatra and Bono were supposed to perform the song live for a recording, due to some technical difficulties, Sinatra became impatient and left early.

5. “Fly Me to the Moon”

Originally titled “In Other Words,” this next song of Frank Sinatra’s songs was written in 1954 by Bart Howard and pushed toward the cabaret industry.

After a while, the song was re-recorded by Kaye Ballard and then Johnny Mathis, which ended up doing well. 

After it was given a bossa nova sound by Joe Harnell in 1962, Frank Sinatra then gave it his spin. It was recorded with Quincy Jones along with the Count Basie Orchestra.

Although the song did not do as well as some of his other songs, it still deserves a chance to be on a list of the best songs by Frank Sinatra. The song was included on the hit album It Might As Well Be Swing.

Related: How Did Frank Sinatra Die? His Final Words, Legacy, and More

6. “Come Fly With Me”

Featured as the title song on his album released in 1958, “Come Fly With Me” was written specifically for Ol’ Blue Eyes. It was created by Jimmy Van Heusen and Sammy Cahn.

Van Heusen was said to have had a passion for air travel and was even a test pilot, so creating this song made complete sense.

The pair also stated that the song was perfect for someone with Sinatra’s reputation for being on the move. It can also be considered sort of a love song if you really listen to the song lyrics.

Because it was considered one of his most popular songs of all time, Sinatra often performed “Come Fly With Me” at concerts. Because of this, it is no surprise that this ballad made it to the top of various charts and remains a favorite in the hearts of listeners everywhere.

7. “New York, New York”

Most people recognize the song as being one of Frank Sinatra’s most popular songs throughout the years. However, the song, written by John Kander and Fred Ebb, was created to be debuted in the movie New York, New York.

What most people do not realize, however, is that the song was originally performed by Liza Minelli in the film. Like other songs not originally performed by Frank Sinatra, it was not until he attached his unique sound that the song became a huge hit.

Released on his album, Trilogy: Past, Present, and Future in 1980, Sinatra also started performing this song in various concerts. This is why it is widely considered one of Sinatra’s best and most popular signature songs of all time.

8. “The Lady is a Tramp”

Another tune written by Richard Rodgers and Lorenz Hart as a show tune for Babes in Arms was performed by Mitzi Green. Like other songs written by these two, “The Lady is a Tramp” has been performed and remastered by many artists over the years.

Interestingly enough, the song was used in the film Pal Joey and performed by Frank Sinatra to Rita Hayworth’s character. The song has also appeared on several of Sinatra’s albums over the years as well as in his live performances.

It should be noted that the song has received various criticisms over the years due to the controversial lyrics and the fact that it wasn’t one of Sinatra’s Christmas songs. Although many people say the lyrics are somewhat offensive to women, several say that it was never the intention of the song. 

9. “My Funny Valentine”

This song by the legendary crooner was originally written by Richard Rodgers and Lorenz Hart in 1937 as a show tune. It was created to be used in the show Babes in Arms and was performed for the first time by Mitzi Green, who was the star of the show.

Although this song was performed by many musicians over the years, Sinatra was said to have the best version, as his voice paired with the rhythm best. Once they reworked some of the parts of the song, it was released in 1954 on his album Songs for Young Lovers.

Like other songs by the Chairman of the Board, “My Funny Valentine” earned him a place on the top of the charts for some time. With the crooner sound Frank Sinatra was known for, the song was the perfect addition to his other hits.

10. “Softly, As I Leave You”

Although this song was made famous by Sinatra, it was actually composed by Tony De Vita and composed by Giorgio Calabrese. The original tune was a chart-topper that was performed by Mino in 1960.

A few years later, in 1964, Frank Sinatra, with the help of Ernie Freeman and Jimmy Bowen, arranged and released his album Softly, As I Leave You. It includes, of course, it’s famous title track. The melody was arranged using a drum kit, keyboards, and backup singers.

Although the changes had been made to the album and title song, it never took off the way they expected it to. This specific song actually stayed at the number 27 spot on Billboard’s Hot 100 list and never moved.

Honorable Mention: “Have Yourself a Merry Little Christmas”

Of course, this list of best Frank Sinatra songs wouldn’t be complete without listing one of Sinatra’s popular Christmas tunes. Unfortunately, his Christmas songs were some of his least favorite tunes. 

Just like Elvis Presley, his manager saw Christmas songs as a way to redeem Sinatra’s questionable character, especially when it came to some of his more illegal dealings in Las Vegas

Little did he know that this song would be the one he is most remembered by over the years, second only to his other hated song, “My Way.” Poor Frank Sinatra. 

But if you like his Christmas tunes better, don’t forget to also check out “White Christmas.”

Other Hit Songs by Frank Sinatra that Didn’t Quite Make the Top 10

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Written by Hope Davis

Long-time music lover Hope became a full-time writer in 2020 after being laid off from her regular job due to COVID-19. She now spends her time traveling the world to see her favorite bands while writing about them!


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