17 Best Songs of the Roaring Twenties: A Timeless Playlist

Step back in time and rediscover the magic of the Roaring Twenties with our definitive list of the best songs from the 20s! This era, a period of unprecedented social and cultural change, birthed a soundtrack as vibrant and revolutionary as the decade itself. From the sultry jazz rhythms that defined speakeasies to the uplifting melodies that filled dance halls, the music of the 1920s left an indelible mark on popular culture, influencing generations of artists to come. Whether you're a seasoned music aficionado or simply curious to explore the sounds that shaped a generation, this curated selection of the best songs from the 20s will transport you to a time of flapper dresses, Charleston dances, and unforgettable melodies. Prepare to be captivated by the timeless charm and undeniable energy of these iconic tracks – a journey through history, one song at a time.

1. Ol' Man River

Paul Robeson's Vocals: Robeson's powerful baritone voice is the undeniable centerpiece of "Ol' Man River" delivering a performance of raw emotion and breathtaking depth that remains iconic even today.

Haunting Melody: The song's melody is both memorable and melancholic, perfectly capturing the weariness and resilience of the characters in *Show Boat*.

Enduring Legacy: "Ol' Man River" transcends its era, becoming a standard for vocalists and a testament to the power of music to express profound human experiences; its inclusion in the 1927 musical *Show Boat* cemented its place in history.

2. Ain't Misbehavin' (Fats Waller)

Swinging Rhythm: Fats Waller's signature piano style drives "Ain't Misbehavin'" a quintessential example of the energetic swing that defined the Jazz Age.

Infectious Melody: The tune is instantly catchy, with a memorable melody that's both playful and sophisticated, perfectly capturing the spirit of the Roaring Twenties.

Vocal Delivery: Waller's smooth vocals add a layer of effortless cool, making "Ain't Misbehavin'" a timeless classic that still resonates with listeners today.

3. West End Blues

Louis Armstrong's Vocals: Armstrong's gravelly, instantly recognizable voice delivers the blues with a raw emotion that perfectly captures the spirit of the roaring twenties.

Trumpet Prowess: His masterful trumpet playing intertwines seamlessly with the vocals, creating a captivating and unforgettable interplay of sound.

Enduring Rhythmic Structure: The song's driving rhythm and bluesy harmonies are both timeless and undeniably danceable, making it a perfect representation of the era's musical landscape.

4. Stardust (Hoagy Carmichael)

Sound: Stardust's mellow, romantic melody is instantly recognizable, perfectly capturing the sophisticated jazz sounds of the 1920s.

Vocals: Hoagy Carmichael's smooth, intimate vocals deliver the lyrics with a heartfelt sincerity that enhances the song's timeless appeal.

Emotional Impact: The song evokes a sense of wistful longing and dreamy romance, making it a perfect soundtrack for a quiet evening reflecting on the era's glamour.

5. In the Jailhouse Now - 2025

Vocal Performance: Jimmie Rodgers' signature yodeling and expressive vocals bring a raw, authentic energy to "In the Jailhouse Now" perfectly capturing the bluesy spirit of the 1920s.

Storytelling: The song's vivid lyrics paint a compelling picture of hardship and confinement, showcasing the power of storytelling in early country music.

Historical Significance: As an early example of the genre's blend of blues and folk influences, "In the Jailhouse Now" offers a glimpse into the musical landscape of the 1920s and the evolution of country music.

6. Crazy Blues (Mamie Smith)

Mamie Smith's Vocals: Smith's powerful and expressive vocals are a defining characteristic of "Crazy Blues" showcasing the raw emotionality that characterized early blues.

Groundbreaking Recording: Released in 1920, this record holds historical significance as one of the first commercially successful blues recordings by a Black female artist, profoundly impacting the music industry.

Infectious Rhythm: The song's driving rhythm and memorable melody are instantly captivating, making it an undeniable dance floor hit of its era and a testament to the enduring power of the blues.

7. Makin’ Whoopee

Upbeat Tempo and Rhythm: "Makin' Whoopee" boasts a relentlessly joyful tempo and infectious rhythm that perfectly captures the exuberance of the Roaring Twenties.

Cantor's Signature Vocals: Eddie Cantor's distinctive, vaudeville-influenced vocals deliver the lyrics with an irresistible energy and playful charm, solidifying its place in the era's musical landscape.

Enduring Popularity: Its catchy melody and celebratory mood ensured its enduring appeal, making it a timeless classic that continues to evoke the spirit of the 1920s.

8. I Wanna Be Loved By You

Vocal Performance: Helen Kane's signature baby-talk vocals are instantly recognizable and quintessential to the flapper era, giving the song a unique charm.

Catchy Melody: The tune is incredibly infectious and easy to sing along to, perfectly embodying the lighthearted spirit of the Roaring Twenties.

Cultural Significance: "I Wanna Be Loved by You" became a massive hit and remains a beloved standard, showcasing the popularity of upbeat jazz and the burgeoning female vocalists of the 1920s.

9. My Man (Fanny Brice - 2025)

Vocal Performance: Fanny Brice's distinctive, powerful vocals are at the forefront, delivering a memorable performance that perfectly embodies the spirit of the roaring twenties.

Lyrical Content: The lyrics, characteristic of the era, explore themes of love and relationships with a directness and emotional honesty that resonates even today.

Historical Significance: "My Man" is a quintessential example of the popular music styles of the 1920s, capturing the energy and unique soundscape of the decade.

10. My Blue Heaven (1927)

Vocal Performance: Paul Whiteman's smooth, sophisticated delivery perfectly embodies the elegance of the Jazz Age, making "My Blue Heaven" a timeless vocal performance.

Orchestral Arrangement: The song's lush orchestral arrangement, a hallmark of Whiteman's style, creates a rich, romantic atmosphere that's captivating even today.

Enduring Popularity: Its simple yet beautiful melody and heartfelt lyrics contributed to its lasting appeal, ensuring "My Blue Heaven" remains a beloved classic of the 1920s.

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  11

  Button Up Your Overcoat

  Ruth Etting

  1929

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  12

  Ain’t We Got Fun?

  Van and Schenck

  1921

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  13

  Sweet Georgia Brown

  Ben Bernie

  1925

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  14

  Bye Bye Blackbird

  Gene Austin

  1926

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  15

  Blue Skies

  Irving Berlin

  1926

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  16

  The Prisoner’s Song

  Vernon Dalhart

  1924

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  17

  Charleston

  Arthur Gibbs

  1923