Frank Sinatra, affectionately known as “Ol’ Blue Eyes” or the “Chairman of the Board,” is a towering figure in American music and culture. His ability to blend jazz with pop sensibilities made him a household name, transcending generations and genres. This article explores the 25 most iconic songs from Sinatra’s extensive 54-year career, showcasing his versatility and enduring appeal.
Who Was Francis Albert Sinatra?
Image source: Wikipedia Commons
Born on December 12, 1915, Sinatra was an American singer and actor whose career spanned several decades. His distinctive voice and charismatic persona made him a symbol of 1950s America, collaborating with legendary musicians and appearing in numerous films.
25 Iconic Frank Sinatra Songs
1. Fly Me To The Moon (1964)
Written by Bart Howard, this song became an unofficial anthem for the Apollo moon landings. Arranged by Quincy Jones, Sinatra’s version swings hard and remains a jazz standard.
2. In The Wee Small Hours Of The Morning (1955)
From the album of the same name, this song captures the essence of romantic longing. Composed by David Mann with lyrics by Bob Hilliard, it’s a quintessential Sinatra track.
3. My Funny Valentine (1954)
Originally from the musical Babes in Arms, Sinatra’s rendition on the Songs For Young Lovers album showcases his collaboration with conductor Nelson Riddle.
4. Somthin’ Stupid (1967)
A duet with his daughter Nancy Sinatra, this folk song became a #1 hit, blending soft pop with Sinatra’s signature style.
5. The Christmas Waltz (1957)
A classic holiday tune written by Sammy Cahn and Jule Styne, featured on the A Jolly Christmas From Frank Sinatra album.
6. Autumn Leaves (1957)
Based on the French song “Les Feuilles Mortes,” Sinatra’s version from the Where Are You? album is one of the most recorded jazz standards.
7. My Way (1969)
With lyrics by Paul Anka, this song reflects on life’s decisions and has become an anthem of personal resilience.
8. The Way You Look Tonight (1964)
From the film Swing Time, this Jerome Kern and Dorothy Fields classic is a timeless love song.
9. The Girl From Ipanema (1967)
A Bossa Nova classic, Sinatra’s duet with Antônio Carlos Jobim showcases the smooth style of the genre.
10. Let It Snow! Let It Snow! Let It Snow! (1950)
A holiday favorite co-written by Jule Styne and Sammy Cahn, featured on the Christmas Songs by Sinatra album.
11. Misty (1962)
Erroll Garner’s instrumental given vocal life by Sinatra, featured on the Sinatra and Strings album.
12. I Thought About You (1956)
A Jimmy Van Heusen and Johnny Mercer composition, this song highlights Sinatra’s ability to convey emotion.
13. Have Yourself A Merry Little Christmas (1957)
Originally written for Meet Me in St. Louis, Sinatra’s version became a beloved holiday classic.
14. It Was A Very Good Year (1966)
Ervin Drake’s song, made famous by Sinatra’s Grammy-winning performance.
15. Three Coins In The Fountain (1954)
From the film of the same name, this Jule Styne and Sammy Cahn tune won an Academy Award.
16. Come Fly With Me (1958)
A title track from one of Sinatra’s most popular albums, written by Jimmy Van Heusen and Sammy Cahn.
17. New York, New York (1980)
Originally from Martin Scorsese’s film, Sinatra’s version became an iconic anthem for the city.
18. Summer Wind (1966)
A pop tune with a big band sound, featuring lyrics by Heinz Meier and Hans Bradtke.
19. Santa Claus Is Comin’ to Town (1948)
A classic Christmas song recorded by Sinatra for his Christmas Songs by Sinatra album.
20. I Get A Kick Out Of You (1953 & 1962)
A Cole Porter tune with lyrics altered after the Hays code, featured on multiple albums.
21. The Brooklyn Bridge (1947)
From the film It Happened in Brooklyn, showcasing Sinatra’s dual talent as a singer and actor.
22. All The Way (1957)
A pop ballad from the film The Joker Is Wild, written by Jimmy Van Heusen and Sammy Cahn.
23. The Best Is Yet To Come (1964)
Cy Coleman and Carolyn Leigh’s song, engraved on Sinatra’s tombstone, from the album It Might As Well Be Swing.
24. You Make Me Feel So Young (1956)
A timeless pop tune from the Songs For Swinging Lovers album, composed by Josef Myrow and Mack Gordon.
25. I Got The World On A String (1953)
A Harold Arlen and Ted Koehler classic, featuring Nelson Riddle’s orchestral arrangement.
Honorable Mentions
- Nancy (with the Laughing Face)
- Strangers In The Night
- Night and Day
- Baubles, Bangles, and Beads
- One For My Baby (And One More For The Road)
- Five Hundred Guys
- Only The Lonely
- Can I Steal A Little Love
- I’ll Follow My Secret Heart
- Moon River
- O Little Town Of Bethlehem
- The Right Girl For Me
- It’s The Same Old Dream
- She’s Funny That Way
- All Of Me
- Silent Night, Holy Night
- Lean Baby
- I’ve Got You Under My Skin
- Jingle Bells
- High Hopes
- If I Had Three Wishes
- It’s A Wonderful World
- White Christmas
- None But The Lonely Heart
- Hello Young Lovers
- (She’s Funny That Way) I Got A Woman Crazy For Me
- That Old Black Magic
- Strange Music
- Indian Summer
- Wave
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