The Great American Songbook. Just the name conjures images of smoky jazz clubs, velvet curtains, and voices that could melt glaciers. But beyond the romanticized image lies a treasure trove of timeless melodies and lyrics that continue to resonate with listeners across generations. Are you ready to delve into the heart of this iconic collection? This list of the best songs from the Great American Songbook isn't just a ranking; it's a journey through musical history, showcasing the artistry and enduring power of these classic compositions. From the heart-wrenching ballads that capture the complexities of love and loss to the upbeat, toe-tapping numbers that celebrate life's joys, these songs offer something for every mood and musical taste. Whether you're a seasoned aficionado or a curious newcomer, prepare to rediscover—or discover for the first time—the magic that makes the Great American Songbook so undeniably captivating. Get ready to revisit some unforgettable classics and perhaps uncover a few hidden gems along the way!
| Song | Artist | Album | Listens |
|---|---|---|---|
| 1. Fly Me To The Moon |
Count Basie Frank Sinatra | Sinatra/Basie: The Complete Reprise Studio Recordings | 175M+ |
| 2. Body and Soul |
Amy Winehouse Tony Bennett | Duets II | 51M+ |
| 3. I've Got You Under My Skin | Frank Sinatra | Chet Baker Sings | 40M+ |
| 4. As Time Goes By | Dooley Wilson | 12M+ | |
| 5. You Make Me Feel So Young | Frank Sinatra | Songs For Swingin' Lovers! (Remastered) | 12M+ |
| 6. Come Fly With Me | Frank Sinatra | This Is Dean Martin | 11M+ |
| 7. Misty | Sarah Vaughan | 10M+ |
1. Fly Me To The Moon (Sinatra/Basie: The Complete Reprise Studio Recordings)
Artistry: Count Basie's big-band arrangement and Frank Sinatra's smooth vocals create a timeless, sophisticated sound perfectly embodying the elegance of the Great American Songbook.
Lyrical Charm: The simple yet evocative lyrics express a universal longing for escape and romance, resonating with listeners across generations.
Enduring Appeal: "Fly Me to the Moon" remains a captivating standard, showcasing the enduring power of classic songwriting and arrangement within the genre's rich history.
2. Body and Soul (Duets II - 2025)
Vocal Synergy: Amy Winehouse's soulful vocals blend seamlessly with Tony Bennett's timeless crooning, creating a captivating duet that showcases the best of both artists' styles.
Timeless Arrangement: The song retains the elegance and sophistication inherent to the Great American Songbook, while Winehouse's unique interpretation adds a fresh layer of emotional depth.
Emotional Resonance: "Body and Soul" delivers a powerful message of devotion and longing, resonating with listeners across generations due to its honest and universal themes of love and loss.
3. I've Got You Under My Skin (1936)
Sinatra's Vocals: Frank Sinatra's velvety baritone is perfectly suited to the song's sophisticated melody, conveying both romantic longing and a touch of playful mischief.
Unforgettable Melody: The instantly recognizable tune, with its memorable rhythm and harmonic shifts, exemplifies the enduring power of Cole Porter's songwriting.
Enduring Appeal: "I've Got You Under My Skin" transcends generations, remaining a timeless classic within the Great American Songbook due to its masterful composition and Sinatra's iconic interpretation.
4. As Time Goes By
Timeless Melody: "As Time Goes By" boasts an instantly recognizable melody that perfectly captures the bittersweet longing of its lyrics, making it a classic of the Great American Songbook.
Dooley Wilson's Vocal Performance: Wilson's rendition in *Casablanca* is iconic, imbuing the song with a soulful depth and emotional weight that elevates it beyond a simple love song.
Enduring Emotional Resonance: The song's enduring appeal lies in its ability to evoke a powerful sense of nostalgia and reflection, resonating with listeners across generations and making it a staple of the American musical canon.
5. You Make Me Feel So Young (Frank Sinatra - 2025)
Sinatra's Vocals: Frank Sinatra's velvety smooth vocals are the heart of "You Make Me Feel So Young" perfectly conveying the song's romantic joy and effortless charm, a hallmark of the Great American Songbook.
Timeless Melody: The melody itself is instantly memorable and undeniably elegant, showcasing the sophisticated simplicity that defines many classic standards.
Orchestral Arrangement: The lush orchestral arrangement complements Sinatra's voice beautifully, adding a layer of richness and sophistication that elevates the song to a truly timeless piece of the American Songbook.
6. Come Fly With Me (Frank Sinatra)
Artist: Frank Sinatra's velvety smooth vocals and impeccable phrasing bring a timeless elegance to this classic.
Melody: The instantly memorable melody is both sophisticated and inviting, perfectly capturing the romanticism of the era.
Orchestration: The lush orchestral arrangement adds a layer of richness and grandeur, complementing Sinatra's performance beautifully and showcasing the best of big band jazz.
7. Misty (Sarah Vaughan)
Sarah Vaughan's Vocals: Sarah Vaughan's interpretation of "Misty" is legendary, showcasing her impeccable phrasing and breath control, making the song both intimate and powerful.
Atmospheric Arrangement: The arrangement perfectly complements Vaughan's vocals, creating a lush and evocative soundscape that perfectly captures the song's melancholic beauty, a hallmark of the Great American Songbook.
Enduring Legacy: "Misty" in Vaughan's rendition remains a timeless classic, continuing to enchant listeners with its sophisticated simplicity and emotional depth, solidifying its place within the canon of the Great American Songbook.
8. Blue Moon (Frank Sinatra)
Sinatra's Vocals: Frank Sinatra's velvety baritone perfectly captures the melancholic beauty of the lyrics, imbuing "Blue Moon" with a timeless, sophisticated charm.
Orchestral Arrangement: The song's lush orchestral arrangement complements Sinatra's vocals, creating a rich and romantic atmosphere that's quintessential Great American Songbook.
Lyrical Imagery: The evocative lyrics paint a picture of longing and hope, making "Blue Moon" a poignant and enduring classic within the genre.
9. Over the Rainbow
Judy Garland's Vocals: Garland's iconic rendition is instantly recognizable for its soaring, emotive power, perfectly capturing the song's yearning and hopeful tone.
Timeless Melody: "Over the Rainbow" boasts a simple yet unforgettable melody that has transcended generations, cementing its place in the American musical landscape.
Enduring Cultural Impact: From its enduring presence in *The Wizard of Oz* to countless covers and reinterpretations, its impact on popular culture remains undeniable, solidifying its status as a Great American Songbook classic.
10. Moon River (1961)
Audrey Hepburn's Vocals: Hepburn's delicate and wistful delivery perfectly captures the melancholic beauty of "Moon River" making it an iconic performance within the Great American Songbook.
Timeless Melody: The song's instantly recognizable melody, with its gentle, flowing rhythm, remains effortlessly captivating and deeply evocative, ensuring its enduring place in popular culture.
Lyrical Simplicity and Impact: The simple yet poignant lyrics, expressing longing and dreams, resonate profoundly, contributing to the song's emotional power and its lasting appeal to listeners across generations.
11My Funny Valentine
Chet Baker
1954
12Unforgettable
Nat King Cole
1991
Unforgettable
13Autumn Leaves
Nat King Cole
1955
14Cheek to Cheek
Fred Astaire
1935
The Essential Fred Astaire
15All the Things You Are
Ella Fitzgerald,Frank Sinatra
1939
16It Had to Be You
Harry Connick Jr.
1989
17Stardust
Hoagy Carmichael
2024
18They Can't Take That Away From Me
Ella Fitzgerald,Louis Armstrong
1937
Ella and Louis
19Someone To Watch Over Me
Ella Fitzgerald
1951
Ella Sings Gershwin
20Love Is Here To Stay
Frank Sinatra
1938
Songs For Swingin' Lovers! (Remastered)
21Night and Day
Frank Sinatra
1942
22I Got Rhythm
George Gershwin
1930
23Let's Face the Music and Dance
Nat King Cole,Fred Astaire
1936
24Summertime
Ella Fitzgerald,Louis Armstrong
1957
Porgy And Bess
25Bewitched, Bothered and Bewildered
Ella Fitzgerald,Doris Day
1940
26Georgia on My Mind
Hoagy Carmichael
1930
27Ain't Misbehavin'
Louis Armstrong
1929
28The Way You Look Tonight
Tony Bennett
2014
Duets II