Step back in time and rediscover the electrifying sounds that defined a generation! This isn't your average "best songs of the 20s" list; we've delved deep into the archives, beyond the obvious hits, to curate a collection that truly encapsulates the raw energy and diverse soundscapes of the roaring twenties. From the sultry jazz vocals that filled smoky speakeasies to the burgeoning sounds of swing and blues that broke new ground, this era birthed musical styles that still resonate today. Why revisit this musical goldmine? Because understanding the music of the 20s offers a fascinating glimpse into the social and cultural shifts of the time, a period of immense change and artistic explosion. Whether you're a seasoned jazz aficionado or simply curious about the sounds that shaped modern music, prepare to be transported back to the heart of the jazz age with our definitive list of the best songs of the 20s. Prepare to be swept away by the irresistible rhythm!
| Song | Artist | Listens |
|---|---|---|
| 1. Ol' Man River | Paul Robeson | 7M+ |
| 2. Ain't Misbehavin' | Fats Waller | 7M+ |
| 3. Stardust | Hoagy Carmichael | 2M+ |
| 4. I’ll See You In My Dreams | Isham Jones | 838K+ |
| 5. Ain’t She Sweet | Gene Austin | 735K+ |
| 6. Sonny Boy | Al Jolson | 381K+ |
| 7. Sweet Georgia Brown | Ben Bernie | 369K+ |
1. Ol' Man River (1927)
A Timeless Classic: Paul Robeson's rendition of "Ol' Man River" remains a powerfully evocative performance, showcasing his incredible vocal range and emotional depth, a defining characteristic of the 1920s.
Unforgettable Vocals: Robeson's resonant baritone voice imbues the song with a gravitas that transcends its era, solidifying its place among the best songs of the decade.
Enduring Impact: The song's enduring popularity speaks to its timeless themes of hardship and resilience, making it a truly unforgettable piece of musical history from the roaring twenties.
2. Ain't Misbehavin' (Fats Waller - 2025)
A Roaring Twenties Classic: Fats Waller's "Ain't Misbehavin'" embodies the exuberant spirit of the Jazz Age, its infectious rhythm and playful lyrics capturing the era's carefree energy.
Unforgettable Vocals and Piano: Waller's distinctive vocals and masterful piano work are unforgettable, showcasing the virtuosity of a true jazz legend.
Timeless Appeal: Despite its age, the song remains remarkably fresh and enjoyable, a testament to its enduring musical quality and catchy melody.
3. Stardust (2024)
Timeless Charm: Stardust, by Hoagy Carmichael, exemplifies the sophisticated elegance of 1920s jazz, showcasing a smooth vocal delivery and memorable melody that effortlessly captures the era's romantic spirit.
Enduring Melody: Its simple yet captivating tune has transcended generations, remaining a beloved standard in American popular music and a testament to Carmichael's songwriting genius.
Jazz Age Icon: Listen to Stardust to experience a quintessential piece of the Jazz Age, its understated sophistication and haunting beauty still resonate deeply today.
4. I’ll See You In My Dreams
A Timeless Classic: Isham Jones' "I'll See You In My Dreams" encapsulates the romanticism and elegance of the 1920s, a sound perfectly representative of the era's musical landscape.
Effortless Melody: The song's simple yet captivating melody is instantly memorable and effortlessly evokes a sense of nostalgia, making it a truly enduring piece.
Perfect for a Roaring Twenties Playlist: This track is essential for any compilation aiming to capture the spirit and sophistication of the Jazz Age.
5. Ain’t She Sweet (Gene Austin - 2025)
A Timeless Classic: Gene Austin's "Ain't She Sweet" embodies the upbeat, joyful spirit of the 1920s, showcasing the era's signature lightheartedness.
Infectious Melody: Its simple yet catchy tune is instantly memorable, a testament to the songwriting prowess of the era.
Vocal Delivery: Austin’s smooth, charming vocals perfectly complement the song's carefree atmosphere, making it a quintessential example of early jazz-influenced pop.
6. Sonny Boy (1928)
A Roaring Twenties Classic: Al Jolson's "Sonny Boy" captures the exuberance and energy of the Jazz Age, showcasing Jolson's powerful vocals and the infectious rhythms characteristic of the era.
Vocal Prowess: Jolson's delivery is nothing short of iconic, his emotional range and showmanship perfectly embodying the spirit of the time.
Enduring Legacy: This track remains a testament to the enduring appeal of early jazz and a crucial piece in understanding the musical landscape of the 1920s.
7. Sweet Georgia Brown
A Defining Sound of the Roaring Twenties: Ben Bernie's "Sweet Georgia Brown" embodies the upbeat, jazzy spirit of the 1920s, its infectious rhythm instantly transporting listeners back to that era.
Unforgettable Melody: The song's simple yet memorable melody, combined with Bernie's smooth vocals, cemented its place in popular culture and continues to resonate today.
Enduring Legacy: Its enduring popularity, evidenced by its countless covers and appearances in film and television, showcases its timeless appeal and why it remains a cornerstone of 1920s music.
8. Bye Bye Blackbird - 2025
A Defining Sound of the Roaring Twenties: Gene Austin's "Bye Bye Blackbird" embodies the era's sophisticated jazz influences, showcasing a smooth vocal delivery and a memorable melody that perfectly captures the spirit of the 1920s.
Enduring Popularity: Its catchy tune and relatable themes of lost love contributed to its widespread popularity and lasting impact on popular music, solidifying its place as a classic.
Timeless Appeal: Even today, "Bye Bye Blackbird" retains its charm, offering a glimpse into the musical landscape of a bygone era and reminding us of the enduring power of simple yet effective songwriting.
9. The Prisoner’s Song
A Defining Sound of the Roaring Twenties: "The Prisoner's Song" captures the raw emotion and stark storytelling prevalent in early country music, perfectly reflecting the era's social and economic anxieties.
Vernon Dalhart's Vocal Prowess: Dalhart's powerful and emotive vocals deliver a performance that is both haunting and unforgettable, establishing a benchmark for early country vocal delivery.
A Cultural Touchstone: This recording's immense popularity cemented its place in music history, making it a quintessential example of the sounds and sentiments that defined the 1920s.
10. April Showers (Al Jolson - 2025)
Al Jolson's Vocal Prowess: April Showers showcases Jolson's signature powerful and emotive vocals, a hallmark of the Jazz Age.
Characteristic 20s Sound: The song's upbeat tempo and jaunty melody perfectly capture the spirit of the roaring twenties, making it instantly recognizable as a product of its time.
Enduring Appeal: Despite its age, "April Showers" retains a timeless quality, demonstrating the enduring power of great songwriting and performance.
11Valencia
Paul Whiteman
1926
12Charleston
Arthur Gibbs
1923