Ol’ Blue Eyes, known to the world as Frank Sinatra, was one of the most popular entertainers of the 40s, 50s, and 60s. A singer, actor, and producer, he could do it all, eventually becoming one of the best-selling musicians of all time by reaching over 150 million record sales worldwide.
Known as a perfectionist, he often recorded tracks in a single take. Ever the performer, his stage presence was utterly unmatched during his time, making him one of the biggest names in entertainment history. In this article, we’ll go over the 31 best songs Frank Sinatra ever recorded.
1. Theme From New York, New York
Theme From New York, New York wasn’t written for Sinatra; it was supposed to be for the score of the Martin Scorsese film New York, New York in 1977 and meant to be sung by Liza Minnelli. She would perform it in the film and in concert, but that didn’t stop Sinatra from recording his own version.
This appeared on his Trilogy: Past Present Future album in 1980 and became his last big hit single. It was so popular it became one of his signature songs, peaking at number 32 in 1980 and earning a Grammy nomination for Best Pop Vocal Performance, Male. To this day, it’s one of the best-known tracks about the city of New York and remains one of the best songs in all of American cinema history.
2. My Way
My Way was another track in Sinatra’s late career that didn’t have the same jazz quality to it that his earlier work did, but it still became one of his signature songs and an iconic track in music history. It started out life as a French pop song by Claude Francois and Jacques Revaux, but Paul Anka put English lyrics to it and gave it to Sinatra. In 1968, Sinatra recorded the song in a single take and then released it on the My Way LP shortly after in 1969.
It made its way to number 27 on the Billboard Hot 100 and number two on the Easy Listening chart in the US. In the UK, it spent 75 weeks in the Top 40, peaking at number five, and then spent another 49 weeks within the top 75 of that chart. While he was apparently not a big fan of the track, it remains to this day an unbroken record on the UK charts and one of his most memorable recordings.
3. That’s Life
That’s Life started out as a popular song by Marion Montgomery, but Sinatra’s version of it became much, much, much more famous. It was released on his 1966 album That’s Life and proved to be an absolutely massive success for him. This reached number four on the Billboard Hot 100 chart and number one on the Easy Listening chart.
Overall, it’s an uplifting track about life that was well ahead of its time. Life happens and things are going to knock you down, but keep your chin up because you’ll be back on top one day. Basically, the jazzy 60s version of modern positivity and slight apathy. In the years since, it has been covered by countless artists like Aretha Franklin, Michael Bublé, Van Morrison, and James Brown. It’s also been a big feature in films and other media since, including the 1995 Casper, 2019 Joker, and Tony Hawk’s Underground 2.
4. The Best Is Yet To Come
The Best Is Yet To Come was originally written by Cy Coleman but became associated with Sinatra after he recorded it for his 1964 album It Might As Well Be Swing. Alongside Count Basie, it would eventually become the last song Sinatra sang in public, and the words “The Best Is Yet To Come” are etched into his tombstone.
While it was originally meant for Tony Bennett, Sinatra was the reason the track became popular in the first place. Fun fact, it was played as the wake-up call for the astronaut crew on the Apollo 10 Mission in 1969, the day a lunar module first flew in solo orbit around the moon and marking the closest approach to the moon in mankind’s history to that date.
5. Fly Me To The Moon
Speaking of the moon… Fly Me To The Moon was first recorded in 1954 by Kaye Ballard. It was a fairly popular song with the jazz cabaret crowd, even before Sinatra put his own personal spin on it. After several artists produced recordings of it, he would record and release his version on his 1964 album It Might As Well Be Swing, and the rest is history.
It came out around the same time as the NASA Apollo missions, the ones that put men on the moon for the first time, and was wildly popular. A copy of his version was sent with the Apollo 10 and 11 missions, the one that orbited the moon and the one that landed on it.
6. Strangers In The Night
What would become the title song of Sinatra’s 1966 album, Strangers In The Night eventually became his most commercially successful single. It rose to number one on the UK Singles chart and the Hot 100 while also breaking into the top 10 of 17 other country’s charts.
His recording of the song won two Grammy Awards, for Best Male Pop Vocal Performance and Record of the Year. It also won Ernie Freeman a Grammy for Best Arrangement Accompanying Vocalist or Instrumentalist. Overall, it is an all-time Ol’ Blue Eyes classic.
7. The Way You Look Tonight
The Way You Look Tonight isn’t just a Frank Sinatra classic, it’s an all-timer. In general, you can think of it as a jazz standard more than any individual artist’s track. Originally performed by Fred Astaire for the film Swing Time, it became a top-seller in 1936. It even won the Academy Award for Best Original Song that year.
The most popular version of the track was of course recorded by Sinatra, who alongside the Nelson Riddle orchestra, produced his version in 1964.
8. Come Fly With Me
One of Sinatra’s earliest songs to find massive success and an enduring legacy, Come Fly With Me served as the title track for his 1958 album. It was a major part of his concert setlists, making it one of his most-performed songs ever and a major standard in music history.
The album as a whole is about traveling, exotic places, and adventures, so this was the perfect tone-setter for it.
9. I’ve Got You Under My Skin
I’ve Got You Under My Skin was originally written by Cole Porter in 1936. That same year, Virginia Bruce performed the song in the musical film Born To Dance, earning a nomination for the Academy Award for Best Original Song. Hundreds of artists have recorded or performed the track over the years, but like many on this list, the Frank Sinatra version has been the most enduring.
It was one of his signature tracks, finding a home on his Songs For Swingin’ Lovers album in 1956 and his 1963 Sinatra’s Sinatra. Even his son, Frank Sinatra Jr. often performs this one in tribute to his late father.
10. High Hopes
High Hopes details the incredible achievements of animals that do things they shouldn’t be able to. It describes them as “pie in the sky,” a phrase meaning much too far out of reach, but implies that they are accomplished in the end, thus attaining their “unreachable” goals.
Sinatra debuted the song alongside Eddie Hodges in the 1959 film A Hole In The Head, earning a Grammy Nomination and winning an Oscar for it. It eventually made its way onto his 1961 album All The Way, peaking at number 30 on the Hot 100 and number six on the UK Singles chart. A slightly different version was recorded by him that was used as the theme song for John F. Kennedy’s 1960 presidential campaign.
11. I’ve Got The World On A String
All musicians tend to have a band or artist that inspired them at a young age and a deep reverence for those who came before. Jazz musicians especially carry this with them. That’s why it’s no surprise that I’ve Got The World On A String was one of the first songs Sinatra recorded once he transferred over to Capitol Records in 1953. His version of the song peaked at number 14 on Billboard’s Most Played list, a revamp of a classic jazz composition by Harold Arlen and Ted Koehler.
12. It Was A Very Good Year
Even someone as legendary as Sinatra had to start somewhere. In his mound of massive hits, It Was A Very Good Year was the first of his recordings to top the Adult Contemporary chart. It also made it to number 28 on the Hot 100. The original version recounted the many women the singer had relationships with in his life, calling each of the years very good and saying each romance was like sweet wine. His version appeared on his September Of My Years album in 1965.
13. Summer Wind
Originally, Summer Wind was released in Germany as Der Sommerwind by Hans Bradtke, but Johnny Mercer translated the song into English lyrics and saw Wayne Newton record it. Sinatra would go on to record the track in 1966 for his Strangers In The Night album. It peaked at number one on the Easy Listening chart and number 25 on the Billboard Hot 100.
14. In The Wee Small Hours of the Morning
Sinatra used In The Wee Small Hours Of The Morning as the title track for his 1955 album. It would go on to be one of the best-selling albums of all time and features often in major publications’ lists of the greatest albums of all time.
A jazz ballad rather than a swinger tune, his recording would forever shape the way singers approached the genre.
15. Change Partners
Sinatra may have been one of the best solo acts in history, but some of his collaborative works are among the best ever as well. Change Partners was a feature on his 1967 album Francis Albert Sinatra & Antônio Carlos Jobim. The cool delivery of Sinatra and the muted music of Jobim were a match made in heaven, giving us a wonderful fusion of Bossa Nova and jazz.
16. Love And Marriage
Sinatra first introduced Love And Marriage in 1955 on Thorton Wilder’s Our Town, going on to record two versions of the track after that performance. These two appeared on his 1956 This Is Sinatra album and his 1965 A Man And His Music album, with the first one eventually becoming the theme song for the sitcom Married… With Children.
17. My Kind Of Town
Originally part of the film score for the 1964 musical Robin And The 7 Hoods, which saw several Rat Pack members star in it, My Kind Of Town was a song that Sinatra made several different recordings of.
He popularized the track, as I’ll say many times in this article, with the version from Sinatra At The Sands in 1966. One cool thing about the song is that each time you hear it, it may have slightly different lyrics, as he switched them up quite often.
18. One For My Baby (And One More For The Road)
One For My Baby (And One More For The Road) was a huge hit for Fred Astaire and featured in the 1943 film The Sky’s The Limit. Sinatra would record the song several times in his career, the first of which came in 1947 with Columbia Records. It ditches the full jazz accompaniment that often backed him in favor of a simple piano.
19. Santa Claus Is Comin’ to Town
Many artists have released Christmas albums over the years, with most great jazz artists doing it once or twice during their careers. Sinatra was no different, recording quite a few classic Christmas songs in his trademark style and releasing them for the world to enjoy. Among those, Santa Claus Is Comin’ To Town may be the one that captures his essence best. This is a mid-tempo, cheery, and bright track recorded by him in 1948.
20. Only The Lonely
Only The Lonely was the hauntingly beautiful and depressing title track of one of Sinatra’s earliest concept albums. Written especially for him in light of his turbulent personal life that saw him finalize a divorce from his second wife, the album artwork featured him dressed up as a crying clown, an aesthetic that matched the theme of the album as a whole.
21. I’ll Never Smile Again
I’ll Never Smile Again was originally written by Ruth Lowe in 1939, eventually becoming a standard in the music world. The best version of the song saw Tom Dorsey And His Orchestra play the instrumentals while Frank Sinatra And The Pied Pipers provided the vocals. You can listen to it on his 1959 No One Cares album.
22. Nancy (With The Laughing Face)
Both Sinatra’s wife—at the time—and daughter were named Nancy, so many people theorized that this song was inspired by one or both of them. The track itself was in fact not for them, as it was originally titled Bessie (With The Laughing Face), but the name change was in honor of his wife and daughter.
Nancy (With The Laughing Face) was first recorded by Sinatra in 1944. Jimmy Van Heusen and Phil Silvers wrote the original but changed the name when playing it at Nancy’s—Sinatra’s daughter—birthday party, upon which Sinatra thought it was written just for her and wanted it.
23. Three Coins in the Fountain
After writing Sinatra popularized a song so much, it’s a bit refreshing to be able to say he was the first to record one. Three Coins In The Fountain was first recorded by him in 1955 for a romance film of the same name, eventually winning him an Oscar for Best Original Song. His recording of it was a number-one hit on the UK charts as well.
Witchcraft was a song Sinatra recorded three separate times, finding its way onto the 1961 All The Way, the 1963 Sinatra’s Sinatra, and Duets in 1993. Its original release peaked at number six on the Billboard Hot 100, remaining on the chart for 16 total weeks. At the very first Grammy Awards, he was nominated for six separate awards. This was nominated for three alone, Song of the Year, Record of the Year, and Best Male Pop Vocal Performance.
25. The Lady Is A Tramp
The Lady Is A Tramp started out as a show tune for the 1937 musical Babes In Arms, a spoof of New York high society that makes fun of the strict social etiquette. Sinatra recorded the song alongside several different artists throughout the 50s and 60s, eventually seeing it become one of his signature tracks and recording new lyric versions like The Gentleman Is A Champ.
26. Here’s That Rainy Day
Dolores Gray was the first to introduce us to Here’s That Rainy Day, doing so in a Broadway musical called Carnival In Flanders. In 1959, Sinatra recorded the song for his album No One Cares and performed it on several TV programs that featured him that year. It eventually became a jazz standard, recorded by numerous other artists like Wes Montgomery and Duke Jordan.
27. My Funny Valentine
My Funny Valentine was first performed when Mitzi Green did it in 1937 during the first showing of Babes In Arms—yep, that one again. Sinatra recorded the track for his 1954 album Songs For Young Lovers and again when he was at Reprise Records. That version remained unreleased until 2009 when the label released the album Seduction: Sinatra Sings Of Love. You’ll find tons of other artists’ versions of the track, including ones from Miles Davis, The Supremes, Dolly Parton, and Bing Crosby.
28. White Christmas
I tried to resist putting more than one of Sinatra’s Christmas songs on the list but I couldn’t help it. White Christmas was first recorded by him in 1944 and was released as a single by him that year. It may very well be the best version of this track ever recorded, with his deep voice and signature delivery adding an extra twinkle of holiday joy to brighten your Christmas celebrations.
29. I’ve Got A Crush On You
I’ve Got A Crush On You has the rather unique distinction of having been used for two different Broadway productions, the only George Gershwin composition to do so. Both Treasure Girl in 1928 and Strike Up The Band in 1930 used the song, but the version Sinatra recorded while at Columbia Records would become the most famous. Over time, it would become a jazz standard and one of the best recordings he ever did.
30. Angel Eyes
If you’re looking for Sinatra at his most emotional and most personal, you’re going to want to listen to Angel Eyes. It was one of the best songs on his 1958 Sings For Only The Lonely album, a penultimate blues track that stands out by not following conventional blues song chords. Like most of his tracks, hundreds of other artists have tried their hand with this one, but each and everyone looks to the Sinatra recording as the standard they compare themselves with.
31. You Make Me Feel So Young
To round out the list, we just had to include this classic Frank Sinatra song. You Make Me Feel So Young was included in his 1956 album Songs For Swingin’ Lovers. It eventually became one of his most-performed tracks, becoming an iconic song in music history. You can also hear it on the soundtrack of the 2003 film, Elf.
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