Frank Sinatra. The name itself conjures images of smoky clubs, suave style, and of course, those unforgettable songs. A true icon, Sinatra transcended the jazz world, becoming a global phenomenon. His impact extends far beyond music, influencing fashion, attitude, and the very definition of cool. For many, Frank Sinatra is the gateway to jazz, a charismatic figure whose music resonates with people who might otherwise overlook the genre. His enduring popularity, decades after his peak, speaks volumes about the power of his voice and the timeless quality of his Sinatra Songs.
This article dives into the discography of “Ol’ Blue Eyes” to explore 25 of his greatest songs. Spanning his remarkable 54-year career, this list showcases the breadth and depth of his musical genius. From swing anthems to tender ballads, and even holiday staples, these are the essential Sinatra songs that define a generation and continue to captivate listeners today.
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The Enduring Legacy of Francis Albert Sinatra
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Image: A black and white publicity photo of a young Frank Sinatra in the 1940s, showcasing his signature style and charisma.
Francis Albert Sinatra, affectionately known as “Ol’ Blue Eyes” or “Chairman of the Board,” was more than just a singer; he was a cultural phenomenon. He emerged during a pivotal era in music history when jazz was transitioning into popular music. While we categorize him as a jazz singer today, in his time, Sinatra was akin to a modern pop star, seamlessly blending music with a successful acting career and moving within influential circles, including connections with figures like Presidents Roosevelt and Kennedy. Sinatra embodied the style, attitude, and spirit of 1950s America.
His musical journey began in 1939 with the Harry James Orchestra, marking the start of an ascent to stardom. Throughout his illustrious career, Sinatra collaborated with a constellation of musical giants, including Tommy Dorsey, Count Basie, Duke Ellington, Ella Fitzgerald, and Antônio Carlos Jobim, among many others.
The 1940s witnessed the phenomenon of “Sinatramania,” a precursor to the Beatlemania of the 60s and the K-Pop craze of today. Sinatra’s appeal resonated deeply with a new generation of teenage girls, dubbed “Bobby Soxers,” who even developed a distinctive style of dress in homage to their idol.
Major record labels recognized his immense talent early on, and Sinatra quickly expanded his reach into musicals and Hollywood films, solidifying his place at the forefront of American pop culture. His career experienced fluctuations, facing both peaks and valleys, yet Sinatra remained a constant force, continually recording, refining his sound, and evolving his artistry over the decades. His dedication cemented his place as one of the most important vocalists in history, and his Sinatra songs continue to be celebrated globally.
25 Essential Frank Sinatra Songs
Let’s delve into 25 of the most iconic recordings from Frank Sinatra’s extensive discography. This list is not ranked, as each song is a classic in its own right, representing various facets of his remarkable career, from Christmas favorites to soundtrack hits. Given Sinatra’s prolific output of over 1,400 recorded songs and 59 solo studio albums, many exceptional recordings couldn’t make this curated list. If your personal favorite isn’t immediately apparent, be sure to check the honorable mentions section at the end—it might just be there!
Let’s explore some of the standout tracks among the vast collection of Sinatra songs.
1. Fly Me To The Moon
“Fly Me To The Moon,” penned in 1954 by Bart Howard, became a popular tune in the years following its release, with numerous artists recording their versions. However, it was Frank Sinatra’s definitive rendition, recorded for his 1964 album It Might As Well Be Swing, that truly cemented its iconic status.
This album, a collaboration with the Count Basie Orchestra, features numerous other classic Sinatra songs that have become staples of his repertoire. Quincy Jones arranged this version of “Fly Me To The Moon,” famously shifting the time signature from 3/4 to 4/4. Sinatra himself insisted on a hard-swinging feel for the track.
Interestingly, in 1968, during the Apollo program, Frank Sinatra’s version of “Fly Me To The Moon” became an unofficial anthem for the lunar missions, adding another layer to its legacy.
Listen to Frank Sinatra’s classic rendition of “Fly Me To The Moon”:
[Video: YouTube link of Frank Sinatra – Fly Me To The Moon]
Explore the chords and musicality of this classic Sinatra song in more detail with our article on Fly Me To The Moon chords.
2. In The Wee Small Hours Of The Morning
“In The Wee Small Hours Of The Morning,” composed by David Mann with lyrics by Bob Hilliard, is a quintessential Sinatra song that debuted on the 1955 album In The Wee Small Hours. This album is often considered a pioneering concept album, exploring themes of solitude, longing, lost love, and heartache.
Album cover for Frank Sinatra's In The Wee Small Hours
Image: The album cover of “In The Wee Small Hours,” featuring a melancholic, nighttime scene that reflects the album’s themes.
The title track, “In The Wee Small Hours Of The Morning,” perfectly encapsulates the album’s mood of romantic yearning and vulnerability. While many artists have since covered the song, Sinatra’s original version remains unmatched in its emotional depth and delivery, making it one of the most poignant Sinatra songs.
Experience the original version of “In The Wee Small Hours Of The Morning” by Frank Sinatra:
[Video: YouTube link of Frank Sinatra – In The Wee Small Hours Of The Morning]
3. My Funny Valentine
“My Funny Valentine” stands as the first show tune on our list of essential Sinatra songs. Originally written by Richard Rodgers and Lorenz Hart for the 1937 musical Babes in Arms, it had already become a beloved standard in American popular music by the time Frank Sinatra recorded it in 1953.
Sinatra’s version of “My Funny Valentine” was featured on his seventh studio album, Songs For Young Lovers, released in 1954 by Capitol Records. This recording marked the beginning of a fruitful collaboration between Sinatra and conductor Nelson Riddle, a partnership that would last for over two decades and shape the sound of many iconic Sinatra songs.
Image: The album cover of “Songs for Young Lovers,” depicting a youthful and romantic Sinatra, aligning with the album’s theme.
Listen to Frank Sinatra’s classic rendition of “My Funny Valentine”:
[Video: YouTube link of Frank Sinatra – My Funny Valentine]
4. Somethin’ Stupid
“Somethin’ Stupid” represents a stylistic departure from the classic swing sound typically associated with early Sinatra songs. Originally a folk song penned by C. Carson Parks, who first recorded it with his wife, Gaile Foote, in 1966, it took on a new life when Frank Sinatra and his daughter, Nancy Sinatra, recorded it as a duet in 1967.
Released as a single, “Somethin’ Stupid” soared to the #1 spot on the Billboard Hot 100 chart for four weeks, demonstrating Sinatra’s continued relevance in the evolving pop music landscape. It later appeared on Frank Sinatra’s album The World We Knew (1967).
This recording leans more towards a soft pop or easy-listening ballad style, showcasing Sinatra’s versatility and ability to adapt to contemporary sounds while maintaining his signature vocal quality. It’s a testament to his cross-genre appeal and enduring presence in pop music, adding a unique flavor to the collection of Sinatra songs.
Image: The album cover for “The World We Knew,” featuring a portrait of Sinatra in a more contemporary, late-1960s style.
Experience Frank and Nancy Sinatra’s charming duet on “Somethin’ Stupid”:
[Video: YouTube link of Frank & Nancy Sinatra – Somethin’ Stupid]
5. The Christmas Waltz
Frank Sinatra’s appeal extends into the realm of holiday music, and “The Christmas Waltz” is a prime example of his festive charm. This song, written specifically for Sinatra in 1954 by Sammy Cahn and Jule Styne, initially appeared on the album White Christmas that same year.
However, it’s the 1957 version from his album A Jolly Christmas From Frank Sinatra that has become the definitive recording. Arranged by Nelson Riddle, this version is imbued with a warm, nostalgic holiday spirit and is considered one of the most iconic Sinatra songs for Christmas.
This album, A Jolly Christmas From Frank Sinatra, is a treasure trove of holiday classics and will reappear several times on this list, solidifying its place as an essential part of the Christmas music canon.
Listen to this iconic Frank Sinatra Christmas song:
[Video: YouTube link of Frank Sinatra – The Christmas Waltz]
6. Autumn Leaves
“Autumn Leaves” is undeniably one of the most recognized jazz standards globally, and among the most frequently recorded jazz songs in history. Frank Sinatra’s rendition stands out as one of the most iconic vocal interpretations of this timeless tune, making it a must-hear among Sinatra songs.
Originally a French song titled “Les Feuilles Mortes,” composed by Joseph Kosma in 1945, it received an English adaptation in 1950 by Johnny Mercer, who renamed it “Autumn Leaves.” Since then, it has been covered countless times, but Sinatra’s version holds a special place in the hearts of many.
Frank Sinatra’s recording of “Autumn Leaves” was featured on his 1957 album Where Are You?, an album dedicated entirely to ballads. This release contrasted sharply with his previous album, A Swinging Affair! (1957), which primarily showcased swing tunes, highlighting Sinatra’s versatility and mastery of different moods within his Sinatra songs.
Album cover for Frank Sinatra's Where Are You?
Image: The album cover for “Where Are You?”, featuring a solitary and reflective Sinatra, perfectly capturing the mood of the ballad album.
Listen to Frank Sinatra’s definitive version of “Autumn Leaves”:
[Video: YouTube link of Frank Sinatra – Autumn Leaves]
Interested in playing this jazz standard? Explore our article on Autumn Leaves chords.
7. My Way
“My Way” is perhaps the quintessential Sinatra song, embodying his signature bravado and independent spirit. Released as a single in 1969, the song is a powerful reflection on life, choices, and personal philosophy.
It speaks of a person looking back on their life’s journey, acknowledging both triumphs and setbacks, and ultimately concluding that they navigated it all by staying true to themselves and doing things “my way.” This theme resonated deeply with audiences and became synonymous with Sinatra’s persona.
Although the melody originates from a French song, “Comme d’habitude,” composed by Jacques Revaux, the English lyrics were specifically crafted for Frank Sinatra, who recorded it and transformed it into a defining piece of his discography. “My Way” has been covered by numerous artists, including Elvis Presley and Sid Vicious, but Sinatra’s version remains the most iconic and recognizable, solidifying its place among the greatest Sinatra songs.
Experience Frank Sinatra’s legendary performance of “My Way”:
[Video: YouTube link of Frank Sinatra – My Way]
8. The Way You Look Tonight
“The Way You Look Tonight” is a timeless classic from the 1936 film Swing Time. With music by Jerome Kern and lyrics by Dorothy Fields, it’s a gem from the Great American Songbook that has been covered by countless singers over the years. However, Frank Sinatra’s rendition is widely considered one of the most iconic and beloved, even among his own impressive catalog of 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, an album that itself features multiple songs on this list, highlighting its collection of award-winning classics.
Image: The album cover for “Sinatra Sings Days of Wine and Roses…”, showcasing Sinatra in a sophisticated and elegant pose, befitting the album’s collection of award-winning songs.
Listen to Frank Sinatra’s definitive version of “The Way You Look Tonight”:
[Video: YouTube link of Frank Sinatra – The Way You Look Tonight]
9. The Girl From Ipanema
“Garota De Ipanema,” internationally known as “The Girl From Ipanema,” is a quintessential Bossa Nova song, embodying the smooth, sophisticated, and romantic essence of the genre. It became a symbol of the Bossa Nova movement’s international appeal, particularly in the United States, where it became a beloved sub-genre of jazz and a cherished jazz standard. Frank Sinatra’s version is a must-listen for anyone exploring Sinatra songs.
Composed by Antônio Carlos Jobim with original Portuguese lyrics by Vinícius de Moraes, the song later received English lyrics by Norman Gimbel, further broadening its appeal.
Image: The album cover for “Francis Albert Sinatra & Antônio Carlos Jobim,” featuring Sinatra and Jobim together, signifying their collaborative album.
While numerous versions exist, Frank Sinatra’s rendition is particularly iconic due to its collaboration with the songwriter himself, Antonio Carlos Jobim. Jobim sings his verses in the original Portuguese, creating a unique and authentic blend of styles. This version was featured on the 1967 album Francis Albert Sinatra & Antônio Carlos Jobim, a landmark collaboration that brought Bossa Nova into the mainstream and added a unique chapter to Sinatra songs.
Experience this iconic duet version:
[Video: YouTube link of Frank Sinatra & Antonio Carlos Jobim – The Girl From Ipanema]
10. Let It Snow! Let It Snow! Let It Snow!
Another festive gem in the Sinatra songs catalog is “Let It Snow! Let It Snow! Let It Snow!” This beloved Christmas classic was composed in 1945 by Jule Styne, with lyrics by Sammy Cahn, and has since become a holiday staple.
Frank Sinatra’s version of “Let It Snow! Let It Snow! Let It Snow!” was initially released as a single in 1950. It featured backing vocals and harmonies by the B. Swanson Quartet, renowned for their Christmas song arrangements, adding a warm, choral dimension to the recording.
Later, it was included in a 1957 re-release of the 1948 album Christmas Songs by Sinatra by Columbia Records. This re-release, titled Christmas Dreaming, also featured the titular Christmas tune “Christmas Dreaming (A Little Early This Year),” enhancing its holiday appeal.
Image: The album cover for “Christmas Songs by Sinatra,” depicting a snowy Christmas scene, perfectly setting the holiday mood.
Listen to Frank Sinatra leading the B. Swanson Quartet in this classic version:
[Video: YouTube link of Frank Sinatra – Let It Snow! Let It Snow! Let It Snow!]
11. Misty
“Misty” is a quintessential jazz standard, originally composed in 1954 as an instrumental piece for Erroll Garner. Later, Johnny Burke added lyrics, transforming it into a vocal piece that quickly became a favorite among jazz singers. Frank Sinatra was among those who embraced it, adding it to his repertoire of Sinatra songs.
Sinatra’s version of “Misty” appeared on his iconic orchestral ballad album Sinatra and Strings, released in January 1962. His rendition is characterized by its lush, romantic arrangement, showcasing the full, rich orchestral sound that became a hallmark of mid-career Sinatra songs. The glossy and expansive production perfectly complements Sinatra’s smooth vocals, creating a truly captivating listening experience.
Album cover for Sinatra and Strings
Image: The album cover for “Sinatra and Strings,” featuring Sinatra conducting an orchestra, visually representing the album’s orchestral focus.
Experience Frank Sinatra’s dreamy rendition of “Misty”:
[Video: YouTube link of Frank Sinatra – Misty]
12. I Thought About You
“I Thought About You” is an American classic dating back to 1939. Composed by Jimmy Van Heusen with lyrics by Johnny Mercer, it’s a song that captures the bittersweet feeling of longing and reminiscence.
Frank Sinatra’s interpretation of this jazz standard first appeared on his 1956 album Songs for Swingin’ Lovers! and is considered classic Sinatra. The entire album features vibrant, swinging arrangements of classic American songbook tunes, masterfully arranged by Nelson Riddle.
This album presented a distinct feel compared to his previous work, such as In The Wee Small Hours (1955), which leaned towards more traditional ballads. Songs for Swingin’ Lovers! showcased Sinatra’s versatility and his ability to deliver both introspective ballads and upbeat swing numbers, further enriching his collection of Sinatra songs.
Album cover for Songs for Swingin' Lovers!
Image: The album cover for “Songs for Swingin’ Lovers!”, depicting Sinatra in a dynamic, swinging pose, reflecting the album’s energetic and upbeat nature.
Listen to Frank Sinatra’s swinging take on “I Thought About You”:
[Video: YouTube link of Frank Sinatra – 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 is often cited as the definitive rendition, making it one of the most beloved Sinatra songs for the holiday season. Originally written by Hugh Martin and Ralph Blane in 1943, the song debuted in the musical Meet Me in St. Louis the following year, sung by Judy Garland.
Garland’s version featured somewhat melancholic lyrics, which were later revised to be more optimistic. However, it was Frank Sinatra’s 1957 version that truly catapulted the song to widespread fame and solidified its place in the Christmas canon.
Image: The album cover for “A Jolly Christmas from Frank Sinatra,” featuring a festive and cheerful Sinatra in a Santa hat, embodying the holiday spirit.
Sinatra’s version, featured on the 1957 album A Jolly Christmas From Frank Sinatra, further modified the lyrics to be even more upbeat and positive, resonating with post-war American optimism. This rendition has become a Christmas staple, played annually during the holiday season and cherished across generations.
Relive the magic of Frank Sinatra’s iconic version:
[Video: YouTube link of Frank Sinatra – Have Yourself A Merry Little Christmas]
14. It Was A Very Good Year
“It Was A Very Good Year” was originally written in 1961 by Ervin Drake, but it was Frank Sinatra’s 1965 recording that transformed it into a classic and one of the most memorable Sinatra songs. Released as a single in 1965 (and appearing on the album September of My Years), Sinatra’s version garnered critical acclaim, earning him a Grammy Award for Best Male Vocal Performance and becoming his first #1 hit in the Adult Contemporary category.
Image of Frank Sinatra's "It Was A Very Good Year" single cover
Image: A vintage single cover for Frank Sinatra’s “It Was A Very Good Year,” showcasing the song’s title and Sinatra’s name.
The song is a poignant reflection on different stages of life, using vintages of wine as metaphors for years gone by. Sinatra’s nuanced and emotional delivery perfectly captures the song’s nostalgic and reflective mood, making it a standout track in his discography.
Listen to Frank Sinatra’s Grammy-winning performance of “It Was A Very Good Year”:
[Video: YouTube link of Frank Sinatra – It Was A Very Good Year]
15. Three Coins In The Fountain
“Three Coins In The Fountain” originated as part of the soundtrack for the 1954 romantic comedy film of the same name. With music by Jule Styne and lyrics by Sammy Cahn, it’s a classic example of a movie theme song that transcends its film origins. Frank Sinatra recorded the version that was featured in the movie, adding it to his impressive list of Sinatra songs.
Sinatra’s rendition of “Three Coins In The Fountain” became a significant hit, winning the Academy Award for Best Original Song the year following the film’s release, further cementing its status as a beloved classic.
/media/File:Three_Coins_in_theFountain(poster_art).jpg)
Image: The film poster for “Three Coins in the Fountain,” featuring romantic imagery from the movie.
Listen to Frank Sinatra’s Oscar-winning version:
[Video: YouTube link of Frank Sinatra – Three Coins In The Fountain]
16. Come Fly With Me
“Come Fly With Me” is a quintessential Sinatra song and one of the first titles that comes to mind when people think of his greatest hits. It became a staple in his live performances, embodying his charismatic stage presence and adventurous spirit.
The music was composed by Jimmy Van Heusen specifically for Frank Sinatra, with lyrics penned by Sammy Cahn. The song served as the title track for Sinatra’s 1958 album of the same name, further enhancing its iconic status. As a piece of classic Americana, “Come Fly With Me” has been featured in numerous film soundtracks, often evoking a sense of wanderlust and classic Hollywood glamour.
Experience the allure of Frank Sinatra’s “Come Fly With Me”:
[Video: YouTube link of Frank Sinatra – Come Fly With Me]
17. New York, New York
“New York, New York” has become indelibly linked with Frank Sinatra, although it was originally written for the 1977 Martin Scorsese film New York, New York. The first recording was by Liza Minnelli, who also starred in the movie, and her version was a hit in its own right. However, it was Sinatra’s interpretation that transformed it into an anthem and one of the most celebrated Sinatra songs.
Frank Sinatra covered “New York, New York” on his 1980 album Trilogy: Past Present Future, and it quickly became iconic. The song became a regular highlight of Sinatra’s live performances, often serving as a show-stopping finale, and it remains a symbol of New York City and Sinatra’s powerful vocal presence.
Listen to Frank Sinatra’s iconic rendition of “New York, New York”:
[Video: YouTube link of Frank Sinatra – New York, New York]
18. Summer Wind
“Summer Wind” began its life as “Der Sommerwind,” a German pop tune written in 1965 by Heinz Meier and Hans Bradtke. Recognizing its catchy melody, English lyrics were soon written to adapt it for American artists.
Frank Sinatra recorded his version in 1966, which appeared on his album Strangers in the Night. This recording is notable for its unique sonic texture, featuring a big band arrangement that includes an organ, adding a distinctive pop sensibility to the tune. “Summer Wind” became a significant hit for Sinatra, reaching number one on the Easy Listening charts and number 25 on the Billboard Hot 100, further demonstrating his ability to blend traditional big band sounds with contemporary pop elements, and adding another dimension to Sinatra songs.
Enjoy Frank Sinatra’s breezy version of “Summer Wind”:
[Video: YouTube link of Frank Sinatra – Summer Wind]
19. Santa Claus Is Comin’ to Town
“Santa Claus Is Comin’ to Town” is another nostalgic Christmas classic in the collection of Sinatra songs. Written in 1934 by J. Fred Coots and Haven Gillespie, it is one of the most frequently recorded Christmas songs, with versions spanning diverse artists from Bruce Springsteen to Michael Bublé and The Jackson 5.
Frank Sinatra’s rendition was released in 1948 on the album Christmas Songs by Sinatra, offering a classic big-band take on this festive favorite.
Listen to Frank Sinatra’s spirited “Santa Claus is Coming To Town”:
[Video: YouTube link of Frank Sinatra – 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, originally written for the 1934 Broadway musical Anything Goes. Frank Sinatra recorded two notable versions of this song—one in 1953 and another in 1962, each reflecting different eras and recording styles of his career.
The earlier 1953 version was recorded during the pre-code Hollywood era, before stricter censorship laws were enforced in popular entertainment. The original lyrics contained a drug reference that was later altered following the implementation of the Hays Code.
The 1962 version, featuring the amended lyrics, was released on the album Sinatra and Swingin’ Brass. This version showcases a more mature and refined Sinatra, backed by a vibrant brass arrangement, adding another layer to the evolution of Sinatra songs.
Album cover for Sinatra and Swingin' Brass
Image: The album cover for “Sinatra and Swingin’ Brass,” featuring a dynamic image of brass instruments, highlighting the album’s brass-focused arrangements.
Listen to Frank Sinatra’s swinging performance of “I Get A Kick Out Of You”:
[Video: YouTube link of Frank Sinatra – I Get A Kick Out Of You]
21. The Brooklyn Bridge
“The Brooklyn Bridge” is a charming song from the 1947 American romantic comedy film It Happened in Brooklyn, which starred Frank Sinatra himself. Columbia Records released the recording as a single in 1947, further leveraging Sinatra’s star power across film and music.
This recording is significant as it underscores Frank Sinatra’s dual appeal as both a singer and an actor. His persona as an American singer is intrinsically linked to his successful Hollywood career. This crossover was a common phenomenon in the early days of cinema, particularly when musicals were a dominant genre, and “The Brooklyn Bridge” exemplifies this synergy within Sinatra songs.
Film poster for It Happened in Brooklyn
Image: The film poster for “It Happened in Brooklyn,” featuring Sinatra and other cast members in a romantic comedy setting.
Listen to Frank Sinatra’s rendition of “The Brooklyn Bridge”:
[Video: YouTube link of Frank Sinatra – The Brooklyn Bridge]
22. All The Way
“All The Way” is a poignant pop ballad from the 1957 film The Joker Is Wild. This song was written by the prolific duo of Jimmy Van Heusen (music) and Sammy Cahn (lyrics), who contributed numerous hits to the American Songbook and to Sinatra songs specifically.
Image: The film poster for “The Joker Is Wild,” featuring Sinatra in his role in the movie.
As the lead actor in The Joker Is Wild, Frank Sinatra sang both “All the Way” and another song for the film. “All the Way,” along with “Chicago (That Toddlin’ Town),” was released as a single in 1957 by Capitol Records. “All The Way” is a testament to Sinatra’s ability to deliver heartfelt ballads, showcasing his vocal control and emotional depth.
Experience Frank Sinatra singing “All The Way”:
[Video: YouTube link of Frank Sinatra – All The Way]
23. The Best Is Yet To Come
Originally written for Tony Bennett by Cy Coleman and Carolyn Leigh in 1959, “The Best Is Yet To Come” became indelibly associated with Frank Sinatra when he recorded it for his 1964 album It Might as Well Be Swing. This album is particularly notable as it was recorded with Count Basie and his Orchestra, bringing together two giants of American music.
Significantly, “The Best Is Yet To Come” holds a special place in Sinatra’s legacy as it was the last song he publicly performed before his death. The words “The Best Is Yet To Come” are even engraved on his tombstone, underscoring its personal significance and lasting message, and making it a powerful addition to Sinatra songs.
Listen to Frank Sinatra’s definitive rendition of “The Best Is Yet To Come”:
[Video: YouTube link of Frank Sinatra – 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 with lyrics by Mack Gordon in 1946. It was originally written for the Hollywood musical Three Little Girls in Blue, released the same year. Frank Sinatra recorded the tune in 1956 for his album Songs For Swingin’ Lovers!, injecting it with his signature energy and charm.
Sinatra’s version proved to be so timeless and universally appealing that it was featured in the 2003 Christmas film Elf, introducing it to new generations and keeping it relevant as one of the cheerful Sinatra songs.
Listen to Frank Sinatra’s spirited performance of “You Make Me Feel So Young”:
[Video: YouTube link of Frank Sinatra – You Make Me Feel So Young]
25. I Got The World On A String
Finally, for the author’s personal favorite among Sinatra songs, we have “I Got The World On A String.” Written in 1932 by Harold Arlen and Ted Koehler, it was already an American classic by the time Frank Sinatra recorded his rendition in 1953.
Sinatra’s version is often cited as the quintessential “Frank Sinatra” song. It features a remarkable orchestral arrangement conducted by Nelson Riddle, showcasing the signature big band sound associated with many classic Sinatra songs. Sinatra’s vocal delivery is brimming with optimism and a carefree attitude, perfectly capturing the spirit of swing-era pop tunes.
Enjoy Frank Sinatra’s vibrant version of “I Got The World On A String”:
[Video: YouTube link of Frank Sinatra – I Got The World On A String]
Honorable Mentions: More Sinatra Songs to Explore
Compiling a list of only 25 of Frank Sinatra’s greatest songs is a challenging task! His vast and rich discography is filled with countless gems. Therefore, we’ve included this list of honorable mentions, showcasing even more exceptional Sinatra songs from his incredible career. Perhaps you’ll find some of your personal favorites here:
- “Nancy (with the Laughing Face)” (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” (1956)
- “Only The Lonely” (Frank Sinatra Sings for Only the Lonely, 1958)
- “Can I Steal A Little Love” (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” (1949)
- “It’s The Same Old Dream” (This Is Sinatra Volume 2, 1958)
- “She’s Funny That Way” (1947)
- “All Of Me” (1948)
- “Silent Night, Holy Night” (A Jolly Christmas from Frank Sinatra, 1957)
- “Lean Baby” (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” (1955)
- “It’s A Wonderful World” (Sinatra Swings, 1961)
- “White Christmas” (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” (1946)
- “Strange Music” (Point of No Return, 1962)
- “Indian Summer” (Francis A. & Edward K., 1968)
- “Wave” (Sinatra and Company, 1971)
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