Frank Sinatra. The name itself conjures images of smoky nightclubs, sharply dressed gentlemen, and a voice that could melt hearts and command attention. Known as “Ol’ Blue Eyes” and “Chairman of the Board,” Sinatra transcends the label of mere singer; he was a cultural icon. While deeply rooted in jazz, his appeal stretched far beyond genre confines, captivating audiences worldwide and solidifying his place in the pantheon of music legends. His journey began in an era where jazz was pop, launching him into superstardom not only for his vocal prowess but also his magnetic stage and screen presence.
For many, Frank Sinatra serves as a gateway into the world of jazz. His charisma and instantly recognizable voice continue to resonate with new generations, long after his passing (December 12, 1915 – May 14, 1998). But what are the quintessential recordings that propelled him to fame and sustained his legendary status throughout his remarkable 54-year career and beyond?
This article delves into 25 of the most iconic songs from Frank Sinatra’s extensive discography. We’ll explore recordings that defined eras, from swinging classics to tender ballads, showcasing the breadth and depth of his artistry. This is your guide to the essential Frank Sinatra songs that every music lover should know.
If you’re a musician inspired by Sinatra’s timeless sound and aspire to master jazz standards, be sure to explore resources like the Learn Jazz Standards Inner Circle to further your musical journey.
Table of Contents
Francis Albert Sinatra: The Voice of an Era
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Image source: Wikipedia Commons
Francis Albert Sinatra, born into a rapidly changing America, became more than just a singer; he became the embodiment of an era. Living through a transformative period in music and entertainment, Sinatra, often called “Ol’ Blue Eyes” or “Chairman of the Board,” was an American singer and actor whose Grammy-winning voice defined generations.
While categorized today as a jazz singer, Sinatra was, in his time, a pop phenomenon. He seamlessly transitioned into Hollywood, associating with figures from presidents like FDR and John F. Kennedy to a diverse tapestry of personalities. His influence extended beyond music and film; he personified the style, attitude, and aspirations of 1950s America.
Sinatra’s professional singing career began in 1939 with the Harry James Orchestra. His talent quickly led him to even greater opportunities. Throughout his illustrious career, he collaborated with a who’s who of musical giants, including Tommy Dorsey, Count Basie, Duke Ellington, Ella Fitzgerald, and Antônio Carlos Jobim, among many others.
The 1940s witnessed “Sinatramania,” a fervent fan frenzy that predated Beatlemania and the K-Pop craze. Sinatra’s charm resonated especially with teenage girls, dubbed “Bobby Soxers,” who even adopted a distinctive style of dress associated with their idol. Major record labels eagerly sought him out, and soon Sinatra was starring in musicals, captivating audiences on the silver screen, and becoming a central figure in American pop culture.
His career wasn’t without its valleys, experiencing periods of slump and resurgence. Yet, throughout it all, Sinatra remained dedicated to recording and refining his sound, constantly evolving while retaining his signature style.
25 Top Frank Sinatra Songs That Define a Legacy
Let’s delve into 25 of the best recordings from Frank Sinatra’s vast discography. This list isn’t ranked by importance, as each song stands as a classic in its own right, encompassing everything from beloved Christmas carols to iconic movie themes. Given Sinatra’s prolific output of over 1,400 recorded songs and 59 solo studio albums, many exceptional recordings couldn’t make this list. If your personal favorite isn’t immediately apparent, be sure to check the honorable mentions at the end – it might just be there!
Here are some standout tracks from the incredible catalog of songs Frank Sinatra gifted the world.
1. Fly Me To The Moon
“Fly Me To The Moon,” a jazz standard beloved across genres, was penned in 1954 by Bart Howard. While many artists recorded it in the subsequent decade, Frank Sinatra’s 1964 rendition remains definitively iconic. It appeared on the album It Might As Well Be Swing, a collaboration with the Count Basie Orchestra, featuring numerous Sinatra classics, several of which are on this list. Quincy Jones arranged this version, famously shifting the time signature from 3/4 to 4/4 at Sinatra’s urging to create a stronger swing feel.
Image source: Wikipedia Commons
In 1968, Sinatra’s “Fly Me To The Moon” gained further iconic status when it became unofficially associated with NASA’s Apollo program, lending its romantic space-themed lyrics to the lunar missions.
Listen to Frank Sinatra’s quintessential version:
For deeper insight into this classic, explore our analysis of the [Fly Me To The Moon chords](https://www.learnjazzstandards.com/blog/fly-me-to-the-moon-chords/).
2. In The Wee Small Hours Of The Morning
“In The Wee Small Hours Of The Morning,” a melancholic masterpiece, was composed by David Mann with lyrics by Bob Hilliard. This signature Frank Sinatra song graced the 1955 album In The Wee Small Hours, widely regarded as one of the first true concept albums in popular music.
In The Wee Small Hours album cover
Image source: Wikipedia Commons
The album delves into themes of loneliness, unrequited love, and heartbreak. The title track, “In The Wee Small Hours Of The Morning,” perfectly encapsulates the album’s mood of romantic longing and vulnerability. Though covered by numerous jazz and pop vocalists, none have quite matched the emotional depth of Sinatra’s original.
Experience Frank Sinatra’s definitive version of “In The Wee Small Hours Of The Morning”:
3. My Funny Valentine
“My Funny Valentine,” a timeless show tune, was written by Richard Rodgers and Lorenz Hart for the 1937 musical Babes in Arms. By the time Frank Sinatra recorded it in 1953, it was already a standard in the Great American Songbook.
Sinatra’s version of “My Funny Valentine” appeared on his seventh studio album, Songs For Young Lovers, released in 1954 by Capitol Records. This recording marked the beginning of Sinatra’s legendary collaboration with conductor and arranger Nelson Riddle, a partnership that would shape his sound for over two decades.
Image source: Wikipedia Commons
Here is Frank Sinatra’s tender rendition of “My Funny Valentine”:
4. Somethin’ Stupid
“Somethin’ Stupid” took a different path to Sinatra’s repertoire. Originally a folk song written and first recorded by C. Carson Parks with his wife, Gaile Foote, in 1966, it became a global phenomenon when Frank Sinatra and his daughter, Nancy Sinatra, recorded it in 1967. Released as a single, their duet soared to the #1 spot on the Billboard Hot 100 for four weeks and was featured on Frank’s album The World We Knew (1967).
Image source: Wikipedia Commons
Stylistically, “Somethin’ Stupid” diverges from Sinatra’s signature swing style, leaning towards soft pop and easy listening. This highlights his versatility and enduring relevance in the ever-evolving landscape of pop music.
Listen to Frank and Nancy Sinatra’s charming performance of “Somethin’ Stupid”:
5. The Christmas Waltz
Frank Sinatra’s appeal extended to the holiday season, and “The Christmas Waltz” is a prime example of his Christmas classics. Written by Sammy Cahn and Jule Styne specifically for Sinatra in 1954, it initially appeared on the album White Christmas that year.
However, the most beloved version of “The Christmas Waltz” is from his 1957 Christmas album, A Jolly Christmas From Frank Sinatra, featuring Nelson Riddle’s lush arrangement. This album is a treasure trove of Christmas nostalgia and appears multiple times on this list.
Experience this iconic Frank Sinatra Christmas song:
6. Autumn Leaves
“Autumn Leaves” stands as one of the most universally recognized jazz standards. Its haunting melody and evocative lyrics have made it one of the most recorded jazz songs in history, and Frank Sinatra’s rendition is arguably the most iconic vocal interpretation.
Based on the French song “Les Feuilles Mortes” by Joseph Kosma from 1945, it gained English lyrics in 1950 by Johnny Mercer, becoming “Autumn Leaves.” Since then, it has been covered countless times, but Sinatra’s version remains a benchmark.
Frank Sinatra’s “Autumn Leaves” graced his 1957 album Where Are You?, a collection of ballads. This album contrasted sharply with his previous release, A Swinging Affair! (1957), which was dominated by upbeat swing tunes, showcasing Sinatra’s dynamic range.
Where Are You album cover
Image source: Wikipedia Commons
Listen to Frank Sinatra’s definitive “Autumn Leaves”:
Interested in playing this jazz standard? Explore our guide to [Autumn Leaves chords](https://www.learnjazzstandards.com/blog/learning-jazz/jazz-advice/autumn-leaves-chords/).
7. My Way
“My Way” is perhaps the quintessential Frank Sinatra anthem, embodying his legendary persona of confidence and self-determination. Released as a single in 1969, the song is a powerful reflection on life’s journey and the choices made along the way.
The song’s narrative is a retrospective look at a life lived with conviction, embracing both triumphs and setbacks, ultimately concluding that despite challenges, success was achieved by doing things “my way.” While the melody originates from the French song “Comme d’habitude” by Jacques Revaux, the English lyrics were specifically crafted for Sinatra, who made it a signature song.
“My Way” has been covered by numerous artists, including Elvis Presley and Sid Vicious, but Sinatra’s version remains the definitive interpretation.
Listen to Frank Sinatra’s iconic “My Way”:
8. The Way You Look Tonight
“The Way You Look Tonight” is a gem from the 1936 film Swing Time. Composed by Jerome Kern with lyrics by Dorothy Fields, it’s a classic of the American Songbook.
Countless singers have interpreted this standard, but Frank Sinatra’s version is among the most celebrated and enduring. It’s a standout even within Sinatra’s own illustrious catalog.
His rendition of “The Way You Look Tonight” was recorded for the 1964 album Sinatra Sings Days of Wine and Roses, Moon River, and Other Academy Award Winners, which includes several other songs featured on this list.
Image source: Wikipedia Commons
Listen to Frank Sinatra’s enchanting “The Way You Look Tonight”:
9. The Girl From Ipanema
“Garota De Ipanema,” known in English as “The Girl From Ipanema,” is a quintessential Bossa Nova song and a defining piece of the genre, capturing its smooth, sophisticated, and romantic essence. Bossa Nova gained significant popularity in the United States, becoming a beloved subgenre of jazz, elevating this song to jazz standard status.
Composed by Antônio Carlos Jobim with original Portuguese lyrics by Vinícius de Moraes, it later received English lyrics by Norman Gimbel, broadening its appeal.
Image source: Wikipedia Commons
While numerous versions exist, Frank Sinatra’s rendition is iconic due to its collaboration with the composer himself, Antônio Carlos Jobim, who sings verses in Portuguese. This version is from the 1967 album Francis Albert Sinatra & Antônio Carlos Jobim, a landmark in cross-cultural musical collaborations.
Experience this iconic duet version:
10. Let It Snow! Let It Snow! Let It Snow!
Another timeless Christmas favorite! “Let It Snow! Let It Snow! Let It Snow!” was composed in 1945 by Jule Styne with lyrics by Sammy Cahn, quickly becoming a holiday standard.
Frank Sinatra’s version of “Let It Snow! Let It Snow! Let It Snow!” was released as a single in 1950 and featured vocal harmonies by the B. Swanson Quartet, renowned for their Christmas arrangements. It was later included in a 1957 reissue of the 1948 album Christmas Songs by Sinatra by Columbia Records. This reissue, titled Christmas Dreaming, also featured the title track “Christmas Dreaming (A Little Early This Year).”
Image source: Wikipedia Commons
Listen to Frank Sinatra and the B. Swanson Quartet in this classic rendition:
11. Misty
“Misty” is a jazz standard renowned for its lush melody, originally written as an instrumental piece in 1954 for Erroll Garner. Johnny Burke later added lyrics, transforming it into a vocal favorite for jazz singers.
Frank Sinatra embraced “Misty,” featuring it on his orchestral ballad album Sinatra and Strings, released in January 1962. Sinatra’s interpretation of “Misty” is characterized by its romantic and opulent orchestral arrangement, a hallmark of his mid-career sound.
Sinatra and Strings album cover
Image source: Wikipedia Commons
Here is Frank Sinatra’s luxurious rendition of “Misty”:
12. I Thought About You
“I Thought About You” is an American classic dating back to 1939, with music by Jimmy Van Heusen and lyrics by Johnny Mercer.
Frank Sinatra’s version of this jazz standard first appeared on his 1956 album Songs for Swingin’ Lovers! and is quintessential Sinatra. The entire album showcases swinging, upbeat arrangements of American Songbook classics, arranged by Nelson Riddle. It presented a different mood compared to his previous album, In The Wee Small Hours (1956), which focused on ballads.
Songs for Swingin' Lovers album cover
Image source: Wikipedia Commons
Listen to Frank Sinatra’s swinging take on “I Thought About You”:
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13. Have Yourself A Merry Little Christmas
“Have Yourself A Merry Little Christmas” is an enduring American Christmas classic, and Frank Sinatra’s version stands as one of the most beloved holiday songs of all time. Originally written in 1943 by Hugh Martin and Ralph Blane, it was first sung by Judy Garland in the 1944 musical Meet Me in St. Louis. Garland’s version featured somewhat somber lyrics, which were later revised to be more optimistic.
Image source: Wikipedia Commons
It was Frank Sinatra’s 1957 recording that propelled “Have Yourself A Merry Little Christmas” to global fame. His version, featured on the album A Jolly Christmas From Frank Sinatra, further tweaked the lyrics to be even more uplifting, solidifying its place as a Christmas staple.
Listen to Frank Sinatra’s iconic version:
14. It Was A Very Good Year
“It Was A Very Good Year” was penned in 1961 by Ervin Drake, but it was Frank Sinatra’s 1965 recording that catapulted it to widespread recognition. Released as a single in 1965 and appearing on the album September of My Years (1965), Sinatra’s rendition earned him a Grammy Award for Best Male Vocal Performance and became his first #1 hit on the Adult Contemporary charts.
Frank Sinatra It Was A Very Good Year single cover
Image source: 45cat
Listen to Frank Sinatra’s poignant “It Was A Very Good Year”:
15. Three Coins In The Fountain
“Three Coins In The Fountain” originated from the 1954 romantic comedy film of the same name, with music by Jule Styne and lyrics by Sammy Cahn. Frank Sinatra recorded the song for the film’s soundtrack.
His version of “Three Coins In The Fountain” won the Academy Award for Best Original Song the following year, further cementing its place in popular culture.
/media/File:Three_Coins_in_theFountain(poster_art).jpg)
Image source: Wikipedia Commons
Listen to Frank Sinatra’s award-winning version:
16. Come Fly With Me
“Come Fly With Me” is a signature Frank Sinatra song and one of the first titles that comes to mind when thinking of his hits. It was a frequent highlight of his live performances.
Jimmy Van Heusen composed the music specifically for Sinatra, with lyrics by Sammy Cahn. The song became the title track of Sinatra’s 1958 album Come Fly With Me. As a quintessential piece of American nostalgia, “Come Fly With Me” has been featured in numerous film soundtracks, evoking a sense of adventure and wanderlust.
Listen to Frank Sinatra’s spirited “Come Fly With Me”:
17. New York, New York
“New York, New York” was initially written for Martin Scorsese’s 1977 film New York, New York. Liza Minnelli, who starred in the movie, first recorded and popularized the song, achieving a hit in her own right.
However, Frank Sinatra’s cover, released on his 1980 album Trilogy: Past Present Future, transformed it into an anthem. “New York, New York” became a staple of Sinatra’s live concerts, and is arguably the version most widely recognized today.
Listen to Frank Sinatra’s iconic rendition of “New York, New York”:
18. Summer Wind
“Der Sommerwind,” the original German version of “Summer Wind,” was a pop tune written in 1965 by Heinz Meier and Hans Bradtke. Recognizing its potential, English lyrics were quickly written to adapt it for American audiences.
Frank Sinatra recorded “Summer Wind” in 1966 for his album Strangers in the Night. The recording is notable for its big band arrangement incorporating an organ, enhancing its pop sensibility. It reached number one on the Easy Listening charts and number 25 on the Billboard Hot 100, demonstrating Sinatra’s continued pop chart success.
Listen to Frank Sinatra’s breezy “Summer Wind”:
19. Santa Claus Is Comin’ to Town
“Santa Claus Is Comin’ to Town” is another timeless Christmas classic, written in 1934 by J. Fred Coots and Haven Gillespie. It’s one of the most frequently recorded Christmas songs, with versions by artists as diverse as Bruce Springsteen, Michael Bublé, and The Jackson 5.
Frank Sinatra’s version was released in 1948 on the album Christmas Songs by Sinatra, contributing to its enduring popularity.
Listen to “Santa Claus Is Comin’ to Town”:
20. I Get A Kick Out Of You
“I Get A Kick Out Of You” is a classic Cole Porter song, written for the 1934 Broadway musical Anything Goes. Frank Sinatra recorded two versions: one in 1953 and another in 1962.
The 1953 recording predates stricter censorship in Hollywood. The original lyrics contained a drug reference that was altered after the Hays Code became more strictly enforced. The 1962 version, featured on the album Sinatra and Swingin’ Brass, presents the amended lyrics.
Sinatra and Swingin' Brass album cover
Image source: Wikipedia Commons
Listen to Frank Sinatra sing “I Get A Kick Out Of You”:
21. The Brooklyn Bridge
“The Brooklyn Bridge” comes from the 1947 American romantic comedy film It Happened in Brooklyn, starring Frank Sinatra. Columbia Records released the recording as a single in 1947 to capitalize on the film’s popularity.
This recording underscores the intertwined nature of Frank Sinatra’s singing and acting careers. His persona as a vocalist was deeply connected to his Hollywood presence, a common phenomenon in early cinema when musicals were a dominant genre.
It Happened in Brooklyn movie poster
Image source: Wikipedia Commons
Listen to Frank Sinatra in “The Brooklyn Bridge”:
22. All The Way
“All The Way” is a poignant ballad from the 1957 film The Joker Is Wild.
Image source: Wikipedia Commons
Written by Jimmy Van Heusen with lyrics by Sammy Cahn, “All The Way” was sung by Frank Sinatra, who starred in the film. Both “All The Way” and “Chicago (That Toddlin’ Town)” from The Joker Is Wild were released as singles in 1957 by Capitol Records, showcasing the film’s musical highlights.
Listen to Frank Sinatra’s heartfelt “All The Way”:
23. The Best Is Yet To Come
Originally written for Tony Bennett in 1959 by Cy Coleman and Carolyn Leigh, “The Best Is Yet To Come” became a Frank Sinatra signature song when he recorded it for his 1964 album It Might as Well Be Swing, famously recorded with Count Basie and his Orchestra.
Notably, “The Best Is Yet To Come” was the last song Frank Sinatra ever performed publicly before his death. The phrase “The Best Is Yet To Come” is even engraved on his tombstone, symbolizing his optimistic spirit.
Listen to Frank Sinatra’s definitive “The Best Is Yet To Come”:
24. You Make Me Feel So Young
“You Make Me Feel So Young” is a classic upbeat tune composed by Josef Myrow with lyrics by Mack Gordon in 1946 for the Hollywood musical Three Little Girls in Blue. Frank Sinatra recorded it in 1956 for his album Songs For Swingin’ Lovers!.
Sinatra’s version has proven timeless, even appearing in the 2003 Christmas film Elf, introducing it to new generations.
Listen to Frank Sinatra’s joyful “You Make Me Feel So Young”:
25. I Got The World On A String
Finally, a personal favorite! “I Got The World On A String” is a standout Frank Sinatra song for many. Written in 1932 by Harold Arlen and Ted Koehler, it was already an American classic when Sinatra recorded it in 1953.
Sinatra’s rendition perfectly embodies the “Frank Sinatra sound.” It features a brilliant orchestral arrangement by Nelson Riddle, and Sinatra’s delivery exudes the optimism and carefree attitude associated with swing-era pop tunes.
Listen to Frank Sinatra’s vibrant “I Got The World On A String”:
Frank Sinatra Songs: Honorable Mentions
Narrowing down Frank Sinatra’s greatest songs to just 25 was a challenge! Here are some honorable mentions from his remarkable career. You might find some of your personal favorites here:
- “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). Explore 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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