Frank Sinatra songs are staples of the Great American Songbook.
Frank Sinatra is one of those jazz singers who is recognized and celebrated outside of jazz. Not only was this due to his breakthrough success as a Hollywood actor, but also because jazz music was pop music in the 40s and 50s.
Today, Frank Sinatra is a bridge into the jazz world for people who might not give jazz a chance otherwise! His iconic personality and charisma give him staying power in pop culture that has far exceeded his lifespan (December 12, 1915 – May 14, 1998).
Getting back to his music career—what are the iconic recordings that catapulted him into the stratosphere and kept him there throughout his incredible career (and long after)?
This article will explore the 25 greatest songs in Frank Sinatra’s discography, looking at his most iconic recordings throughout his 54-year career!
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Table of Contents
Who Was Francis Albert Sinatra?
image source: Wikipedia Commons
Frank Sinatra, nicknamed Ol’ Blue Eyes or Chairman of the Board, was an American singer and Grammy Award-winning recording artist who lived through and evolved in an incredibly influential period in music and entertainment history.
We consider Frank Sinatra a jazz singer today, but he was more akin to a pop star who acted in movies and rubbed elbows with all sorts of characters—like Presidents FDR and John F. Kennedy. Not only was he revered for his music and acting, but he personified the style and attitude of 1950s America.
He started singing for the Harry James Orchestra in 1939, but it wouldn’t be long before he moved on to bigger and better things. Throughout his career, he worked with various musicians, including Tommy Dorsey, Count Basie, Duke Ellington, Ella Fitzgerald, and Carlos Antonio Jobim (to name a few).
The 1940s was known for Sinatramania, which preceded Beatle Mania and the love of K-Pop. He appealed to a new generation of teenage girls, who were nicknamed Bobby Soxers, for a new style of dress associated with them.
Major record labels were quick to sign him, and it wasn’t long before he was singing in musicals, acting in movies, and sitting front and center in American pop culture.
His career had many ups and downs, various slumps and revivals, but he persistently recorded and refined his sound, which evolved over the years.
The 25 Best Frank Sinatra Songs
Let’s examine the best recordings from the Frank Sinatra discography. This list isn’t in a particular order of importance, as all of these songs are classics in their own right and will cover everything from Christmas songs to songs from movie soundtracks.
Many great recordings aren’t on this list because Sinatra recorded over 1,400 songs and released 59 studio albums as a solo artist! Prolific is an understatement! If you don’t see your favorite on the list, be sure to check the honorable mentions at the end! There is a good chance you’ll find it there.
Let’s dig into a few songs that stand out (from the over 1,400 he’s recorded).
1. Fly Me To The Moon
Fly Me To The Moon was written in 1954 by songwriter Bart Howard. Numerous artists recorded and released this song in the decade following its publication. However, the iconic Frank Sinatra version would be recorded and released on the 1964 album It Might As Well Be Swing.
This album was recorded with the Count Basie Orchestra and includes many other classic Frank Sinatra songs (some of which are on this list). This version of Fly Me To The Moon was arranged by Quincy Jones, who changed the tune’s time signature from 3/4 to 4/4.
It was Frank Sinatra’s insistence that it swing hard.
In 1968, when the Apollo program launched, Frank Sinatra’s version of Fly Me To The Moon became an unofficial anthem for the subsequent flights to the moon!
Check out Frank’s classic version:
For more on this classic Frank Sinatra song, check out our article on the Fly Me To The Moon chords.
2. In The Wee Small Hours Of The Morning
“In The Wee Small Hours Of The Morning” was composed by David Mann, and the lyrics were by Bob Hilliard. This classic Frank Sinatra song debuted on the 1955 album In The Wee Small Hours, considered one of the first bona fide concept albums.
image source: Wikipedia Commons
The album explores themes of longing, unrequited love, and failed relationships. Its title track, “In The Wee Small Hours Of The Morning,” is a perfect example of the romantic angst and limerance found throughout.
The song went on to be recorded by many other jazz and pop singers, but no version matched Frank’s original.
Check out Frank’s original version of “In The Wee Small Hours Of The Morning:”
3. My Funny Valentine
“My Funny Valentine” is our first show tune on the list. Richard Rodgers and Lorenz Hart wrote it for the 1937 musical Babes in Arms. When Frank Sinatra recorded it in 1953, it was already a fixture in popular American music.
The Frank Sinatra version of “My Funny Valentine” appeared on his seventh studio album, Songs For Young Lovers, released in 1954 by Capitol Records.
“My Funny Valentine” and the album Songs For Young Lovers mark Frank Sinatra’s first collaboration with conductor Nelson Riddle, a musical partnership lasting over twenty years.
image source: Wikipedia Commons
Here is Frank Sinatra’s rendition of “My Funny Valentine:”
4. Somthin’ Stupid
“Somthin’ Stupid” was a folk song written by C. Carson Parks, who recorded the original version with his wife, Gaile Foote, in 1966. One year later, Frank Sinatra and his daughter, Nancy Sinatra, recorded and released Somthin’ Stupid as a single, which spent four weeks in the #1 spot on the Billboard Top 100.
It would later appear on the Frank Sinatra album The World We Knew (1967).
Stylistically, this recording departs from the classic crooning swing of earlier Frank Sinatra recordings. It is better described as a soft pop or easy-listening ballad, displaying Frank Sinatra’s cross-genre appeal and staying power in pop music.
image source: Wikipedia Commons
Check out Frank and Nancy Sinatra performing “Somthin’ Stupid:”
5. The Christmas Waltz
There are many dimensions to Frank Sinatra’s appeal, and one of them is centered firmly around the Holidays. This isn’t the only Frank Sinatra Christmas song on this list, but it’s definitely an iconic one that deserves recognition.
Songwriters Sammy Cahn and Jule Styne wrote “The Christmas Waltz” for Frank Sinatra in 1954. It first appeared on the album White Christmas that year.
However, Frank recorded a few versions of the song, and the most iconic one comes from his 1957 Christmas album A Jolly Christmas From Frank Sinatra, which featured an arrangement by Nelson Riddle.
This album will appear a few times on this list and is filled to the brim with classic Christmas nostalgia.
Check out this iconic Frank Sinatra Christmas song:
6. Autumn Leaves
Autumn Leaves is undoubtedly one of the most famous jazz standards of all time. It is one of the most recorded jazz songs in history. Frank Sinatra’s version is easily one of this tune’s most iconic vocal versions.
Based on the French tune “Les Feuilles Mortes” by Joseph Kosma in 1945, this French song received an English makeover in 1950 by Johnny Mercer, who rechristened it “Autumn Leaves.” Since then, it has been covered and recorded countless times.
Frank Sinatra’s version appeared on the 1957 album Where Are You?, which consisted of all ballads. This album juxtaposed his prior album, A Swinging Affair (1957), which primarily consisted of swing tunes.
image source: Wikipedia Commons
Check out Frank Sinatra’s version of Autumn Leaves:
Want to learn how to play Autumn Leaves? Check out this article on Autumn Leaves chords.
7. My Way
“My Way” is an iconic Frank Sinatra song that exemplifies his bravado and demeanor. This single, released in 1969, is about a person reflecting on their life’s directions and the decisions they made to get there.
It’s essentially a metaphorical retrospective on the ups and downs of his career, where the character in the song ultimately concludes that despite the hardships and challenges, he made it through because he did it his way.
Though the music comes from a French song, “Comme d’habitude,” composed by Jacques Revaux, the English lyrics were expressly written with Frank Sinatra in mind, who recorded it and made it a staple of his discography.
Other artists like Elvis Presley and Sid Vicious would go on to cover this iconic tune.
Check out Frank Sinatra’s “My Way:”
8. The Way You Look Tonight
“The Way You Look Tonight” is a song from the 1936 film Swing Time. The music was composed by Jerome Kern, and the lyrics were by Dorothy Fields.
Numerous singers have covered and recorded the American Songbook classic over the years, but Frank Sinatra’s version is one of the most iconic and popular. It even stands out as an iconic Frank Sinatra song among iconic Frank Sinatra songs!
His version was recorded and released on the 1964 album Sinatra Sings Days of Wine and Roses, Moon River, and Other Academy Award Winners, which also features other entrants on this list.
image source: Wikipedia Commons
Check out Frank Sinatra’s version of “The Way You Look Tonight:”
9. The Girl From Ipanema
“Garota De Ipanema,” or “Girl From Ipanema,” is a Bossa Nova classic and a poster child for the smooth style and mood of the Bossa Nova movement. Bossa Nova took off in the United States and became a staple sub-genre of jazz, making this tune a beloved Jazz Standard.
This song was composed by Antônio Carlos Jobim and originally featured Portuguese lyrics by Vinícius de Moraes. Norman Gimbel later wrote the English lyrics.
image source: Wikipedia Commons
Though there are many versions of this tune, the Frank Sinatra version is iconic because it is a duo with the songwriter Antonio Carlos Jobim, who sings his verses in the original Portuguese. This version appeared on the 1967 album Francis Albert Sinatra & Antônio Carlos Jobim.
Here is the iconic duo version:
10. Let It Snow! Let It Snow! Let it Snow!
Another classic Christmas song! This iconic song was composed in 1945 by Jule Styne, with lyrics by Sammy Cahn.
Frank Sinatra’s version of “Let It Snow! Let It Snow! Let It Snow!” was released in 1950 as a single and featured a chorus and harmony support by the B. Swanson Quartet, who were known for their Christmas song arrangements.
It would later be added to a 1957 rerelease of the 1948 album Christmas Songs by Sinatra Columbia Records. This rerelease would be called Christmas Dreaming and also included the titular Christmas tune “Christmas Dreaming (A Little Early This Year).”
image source: Wikipedia Commons
Check out Frank Sinatra leading the B. Swanson Quartet in this classic version:
11. Misty
“Misty” is a classic jazz standard written in 1954 for Erroll Garner. Initially, it was an instrumental song, but Johnny Burke later added lyrics, and it soon became a heavily recorded song of choice by many jazz singers.
Frank Sinatra was one of them! It appeared on his iconic orchestral ballad album Sinatra and Strings, released in January 1962. Frank’s version of “Misty” is lush and romantic. It possesses that full, glossy orchestral sound that would become an iconic hallmark of mid-career Frank Sinatra’s songs.
image source: Wikipedia Commons
Here is Frank Sinatra’s rendition of “Misty:”
12. I Thought About You
“I Thought About You” is an American classic from 1939. It was composed by Jimmy Van Heusen and featured lyrics by Johnny Mercer.
Frank Sinatra’s version of this classic jazz standard first debuted on the 1956 album Songs for Swingin’ Lovers and is classic Frank. This whole album features swinging, poppy arrangements of classic American songbook tunes arranged by Nelson Riddle.
It had a different feel to his previous album, In The Wee Small Hours (1956), which consisted of more traditional ballads.
image source: Wikipedia Commons
Check out Frank Sinatra on “I Thought About You:”
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13. Have Yourself A Merry Little Christmas
“Have Yourself A Merry Little Christmas” is an American Christmas classic, and Frank Sinatra’s version stands out as one of the top Christmas songs of all time. This song was originally written by Hugh Martin and Ralph Blane in 1943.
Judy Garland debuted this song in the musical Meet Me in St. Louis the following year after revising the lyrics to make them more positive. This song became a Christmas hit but may have faded into history if it hadn’t been for Frank Sinatra’s 1957 version.
image source: Wikipedia Commons
Frank’s version, which further modified the lyrics toward the positive, catapulted this song into the stratosphere. It appeared on the 1957 album A Jolly Christmas From Frank Sinatra and has been a Christmas staple.
Though it is no doubt familiar to you, here is Frank Sinatra’s iconic version:
14. It Was A Very Good Year
“It Was A Very Good Year” was written in 1961 by Ervin Drake. However, Frank Sinatra’s 1966 version made this song famous. This version, released as a single, netted Frank a Grammy Award for Best Male Vocal Performance and became Frank’s first #1 hit in the Adult Contemporary category.
image source: 45cat
Check out Frank on “In Was A Very Good Year:”
15. Three Coins In The Fountain
“Three Coins In The Fountain” is a song by Jule Styne and features lyrics by Sammy Cahn. It was part of the soundtrack for the 1954 romantic comedy of the same name. Frank Sinatra recorded the song that would be used in the soundtrack.
His version won the Acadamy Award for Best Original Song the following year.
image source: Wikipedia Commons
Check out Frank’s version:
16. Come Fly With Me
“Come Fly With Me” is a Frank Sinatra classic and is one of the top Frank Sinatra songs that come to mind when people are asked to name his hits. It was often included in his set list in live performances.
Jimmy Van Heusen wrote the music specifically for Frank Sinatra, and Sammy Cahn penned the lyrics. The song appeared as the title track on Frank’s 1958 album of the same name. As a classic piece of American nostalgia, this song has appeared in numerous film soundtracks over the years.
Check out Frank Sinatra’s “Come Fly With Me:”
17. New York, New York
“New York, New York” was originally written for the 1977 film New York, New York, directed by Martin Scorsese. The original recording featured Liza Minelli, who also starred in the movie. Her version was a hit in its own right.
However, Frank Sinatra covered it on his 1980 album Trilogy: Past Present Future, and it became iconic.This song regularly appeared on Frank’s setlist during live performances.
Check out Frank on his classic song, “New York, New York:”
18. Summer Wind
“Der Sommerwind” was originally a German pop tune written in 1965 by Heinz Meier and Hans Bradtke. However, the lyrics were soon rewritten in English so American artists could capitalize on this infectious pop tune.
Frank recorded a version in 1966 that would appear on his album Strangers in the Night. Sonically, this recording is interesting as it features a big band with an organist, which adds to this tune’s pop appeal. It would hit number one on the Easy Listening charts and 25 on the Billboard Top 100.
Check out Frank’s version of “Summer Wind:”
19. Santa Claus Is Comin’ to Town
“Santa Claus Is Coming To Town” is another nostalgic Christmas classic written in 1934 by J. Fred Coots and Haven Gillespie. This is one of the most recorded Christmas songs, with diverse artists such as Bruce Springsteen, Micheal Buble, and the Jackson 5 having versions of their own.
Frank’s version was released in 1948 on the Album Christmas Songs by Sinatra.
Check out “Santa Claus is Coming To Town:”
20. I Get A Kick Out Of You
“I Get A Kick Out Of You” is a classic Cole Porter tune written for the 1934 Broadway musical Anything Goes. Frank Sinatra recorded two versions of the song—one in 1953 and another in 1962.
The earlier version was recorded in pre-code Hollywood before censorship laws entered popular entertainment. The original lyrics contained a drug reference that would later be altered after the Hays code was enacted.
The 1962 version featured the amended lyrics, released on the album Sinatra and Swingin’ Brass.
image source: Wikipedia Commons
Check out Frank Sinatra singing “I Get A Kick Out Of You:”
21. The Brooklyn Bridge
“The Brooklyn Bridge” is a song from the 1947 American romantic comedy film It Happened in Brooklyn, which starred Frank Sinatra. Columbia Records released the recording as a single in 1947.
This recording is significant because it shows Frank Sinatra’s appeal as a singer and an actor. His persona as an American singer is inextricably linked to his career in Hollywood. This crossover trend was very common in the early days of cinema when musicals were the norm.
image source: Wikipedia Commons
Check out Frank on “The Brooklyn Bridge:”
22. All The Way
“All The Way” is a pop ballad from the movie The Joker Is Wild (1957).
image source: Wikipedia Commons
“All the Way” was written by Jimmy Van Heusen and featured lyrics by Sammy Cahn. Frank Sinatra, the film’s lead, sang this and another song for The Joker Is Wild. Both “All the Way” and “Chicago (That Toddlin’ Town)” were released as singles in 1957 by Capitol Records.
This song is another great example of Frank’s crossover appeal. Check out Frank singing “All The Way:”
23. The Best Is Yet To Come
Originally written for Tony Bennet by Cy Coleman and Carolyn Leigh in 1959, this song became a Frank Sinatra classic when he recorded it for his 1964 album It Might as Well Be Swing. This album is iconic because it was recorded with Count Basie and his Orchestra.
Significantly, this was the last song Frank Sinatra publicly performed before his death. The words “The Best Is Yet To Come” are even engraved on his tombstone!
Check out Frank’s iconic rendition of “The Best Is Yet To Come:”
24. You Make Me Feel So Young
“You Make Me Feel So Young” is a classic pop tune composed by Josef Myrow and written by Mack Gordon in 1946 for the Hollywood musical Three Little Girls in Blue, which came out that same year. Frank Sinatra recorded the tune in 1956 for his album Songs For Swinging Lovers.
Frank’s version was so timeless that it appeared in the 2003 Christmas film Elf.
Check out Frank Sinatra on “You Make Me Feel So Young:”
25. I Got The World On A String
Now it’s time for the author’s choice! I Got The World On A String is my favorite Frank Sinatra song. Written in 1932 by Harold Arlen and Ted Koehler, it was already an American classic when Frank recorded it in 1953.
Frank’s rendition is one of the clearest examples of a “Frank Sinatra” song. It has an incredible orchestral arrangement conducted by Nelson Riddle. Frank’s delivery is brimming with the optimism and carefree demeanor I associate with swingin’ pop tunes from the era.
Check out Frank Sinatra’s version of “I Got The World On A String:”
Frank Sinatra Songs: Honorable Mentions
Limiting our list to 25 of Frank Sinatra’s greatest songs was very difficult! That’s why we’ve included this list of honorable mentions from Frank Sinatra’s incredible career. See if your favorites are below:
- “Nancy (with the Laughing Face)” – single released from Columbia Records (1944)
- “Strangers In The Night” – Strangers in the Night (1966)
- “Night and Day” – Sinatra and Strings (1962)
- “Baubles, Bangles, and Beads” – Come Dance With Me (1959)
- “One For My Baby (And One More For The Road)” – Frank Sinatra Sings Harold Arlen (1964)
- “Five Hundred Guys” – single released from Capitol Records (1956)
- “Only The Lonely” – Frank Sinatra Sings for Only the Lonely (1958)
- “Can I Steal A Little Love” – single released from Capitol Records (1957)
- “I’ll Follow My Secret Heart” – Sinatra Sings Great Songs From Great Britain (1962)
- “Moon River” – Sinatra Sings Days of Wine and Roses, Moon River, and Other Academy Award Winners (1964). Check out this article to learn the Moon River chords.
- “O Little Town Of Bethlehem” – A Jolly Christmas from Frank Sinatra (1957)
- “The Right Girl For Me” – single released from Columbia Records (1949)
- “It’s The Same Old Dream” – This Is Sinatra Volume 2 (1958)
- “She’s Funny That Way” – single released by Columbia Records (1947)
- “All Of Me” – single released by Columbia Records (1948)
- “Silent Night, Holy Night” – A Jolly Christmas from Frank Sinatra (1957)
- “Lean Baby” – Capitol Records (1953)
- “I’ve Got You Under My Skin” – Songs for Swingin’ Lovers! (1956)
- “Jingle Bells” – Christmas Songs By Sinatra (1948)
- “High Hopes” – All the Way (1961)
- “If I Had Three Wishes” – single released by Capitol Records (1955)
- “It’s A Wonderful World” – Sinatra Swings (originally Swing Along with Me) (1961)
- “White Christmas” – single released by Capitol Records (1954)
- “None But The Lonely Heart” – Dedicated to You (1950)
- “Hello Young Lovers” – September of My Years (1965)
- “(She’s Funny That Way) I Got A Woman Crazy For Me” – Songs by Sinatra (1947)
- “That Old Black Magic” – single released by Columbia Records (1946)
- “Strange Music” – Point of No Return (1962)
- “Indian Summer” – Francis A. & Edward K (1968)
- “Wave” – Sinatra and Company (1971)
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