31 Greatest & Most Famous Songs About the 20s (Roaring List)

Songs from the 1920s encapsulate the energy, optimism, and transformative spirit of a decade known as the Jazz Age. Through vibrant jazz, heartfelt blues, and lively dance tunes, 1920s music celebrates both the carefree and complex sides of the Roaring Twenties.

These songs not only entertained but also echoed the era’s social changes, with themes of liberation, resilience, and love that remain relevant today.

From timeless classics to pioneering sounds, music from the 1920s continues to capture the essence of a dynamic period in history, offering listeners a window into the soul of a rapidly evolving world.

31 Most Popular Songs About the 1920s That You Must Hear (Ultimate Playlist)

These songs encapsulate the spirit of the 1920s, reflecting the cultural and musical innovations of the time.

The 1920s, often referred to as the “Roaring Twenties,” was a vibrant era that produced numerous timeless musical pieces. Here is a curated list of 31 notable songs from that decade:

#1 “Swanee” by Al Jolson

“Swanee,” performed by Al Jolson, became one of the iconic songs of the early 1920s, capturing the era’s vibrant spirit and love for show tunes. Originally written by George Gershwin and Irving Caesar, the song features lively rhythms and a catchy melody that quickly became a hit, evoking a sense of longing for the American South with lines about the Swanee River.

Jolson’s powerful, emotive voice brought a sense of nostalgia and excitement to the song, making it an anthem for audiences who yearned for both the glamour of the Jazz Age and the warmth of home. “Swanee” showcases the theatricality and energy that defined much of 1920s music, marking Jolson as a beloved star of the decade.

#2 “Whispering” by Paul Whiteman and His Orchestra

Paul Whiteman’s “Whispering” was a groundbreaking hit that introduced many Americans to the sophisticated, smooth sounds of early jazz. With its gentle melody and subtle syncopation, the song showcased Whiteman’s talent for blending classical influences with jazz, earning him the title “King of Jazz.”

The success of “Whispering” paved the way for jazz’s mainstream acceptance, setting the tone for the music that defined the Roaring Twenties. Whiteman’s orchestra became a sensation, and the song’s soft, romantic sound resonated with audiences eager for music that combined elegance with modern flair. “Whispering” remains a defining piece of 1920s music, capturing the beauty and innovation of the era’s evolving soundscape.

#3 “Ain’t We Got Fun?” by Van and Schenck

“Ain’t We Got Fun?” by the duo Van and Schenck is a playful, lighthearted song that captures the carefree attitude often associated with the 1920s. With witty lyrics that highlight both the struggles and joys of everyday life, the song humorously embraces the idea of living in the moment, regardless of financial hardship.

The song’s catchy melody and optimistic tone made it an instant hit, resonating with audiences facing post-war economic challenges. “Ain’t We Got Fun?” embodies the resilience and positivity of the Roaring Twenties, reminding listeners that even in tough times, there is joy to be found. The song became an anthem for the era’s “live for today” attitude, reflecting the spirit of a generation.

#4 “April Showers” by Al Jolson

Al Jolson’s “April Showers” is a tender, hopeful ballad that became an emblem of optimism during the 1920s. The song’s lyrics compare life’s challenges to spring rain, suggesting that better days are always ahead, and Jolson’s passionate delivery added a touch of heartfelt sincerity that resonated with listeners.

The melody’s gentle rise and fall mirrors the ebb and flow of life, making it a comforting and uplifting piece. “April Showers” became a favorite for audiences who found solace in its message of resilience, especially in a decade marked by both prosperity and hardship. Jolson’s warm, expressive voice made the song a classic, capturing the emotional highs and lows of the Roaring Twenties.

#5 “My Man” by Fanny Brice

Fanny Brice’s “My Man” is a powerful ballad of unrequited love and devotion, showcasing Brice’s emotional depth and vocal prowess. Originally a French song, “Mon Homme,” Brice’s English version brought it to American audiences, where her vulnerable, heartfelt performance left an indelible mark on the decade.

The lyrics tell the story of a woman’s unwavering love for a man who doesn’t reciprocate, and Brice’s voice conveys both the pain and beauty of her character’s feelings. “My Man” became a signature song for Brice, highlighting her ability to bring authenticity and emotion to the stage. Her performance resonated with audiences, making it one of the decade’s most memorable songs about love and heartbreak.

#6 “Toot, Toot, Tootsie! (Goo’ Bye)” by Al Jolson

“Toot, Toot, Tootsie! (Goo’ Bye),” performed by Al Jolson, is an upbeat and lively song that quickly became a hit in the 1920s. With its infectious rhythm and playful lyrics, the song captures the excitement and energy of the decade, as Jolson sings about saying goodbye with an optimistic, cheerful spirit.

The song’s catchy melody and Jolson’s charismatic delivery made it a favorite at parties and social gatherings, embodying the carefree attitude of the Jazz Age. “Toot, Toot, Tootsie!” reflects the era’s embrace of fun, freedom, and celebration, as people reveled in new social norms and cultural changes. Jolson’s performance turned the song into an enduring classic, showcasing the joyful exuberance that defined the Roaring Twenties.

#7 “Yes! We Have No Bananas” by Billy Jones

Billy Jones’s “Yes! We Have No Bananas” is a humorous, upbeat song that became an unexpected cultural phenomenon in the 1920s. The song’s catchy chorus and absurd lyrics about a fruit shortage made it both a novelty hit and a lighthearted reflection on the quirks of daily life, resonating with audiences who appreciated its playful spirit.

As people were drawn to its infectious energy, the song became a pop culture staple, inspiring catchphrases, cartoons, and references throughout the decade. “Yes! We Have No Bananas” embodies the fun and whimsy of the Jazz Age, a time when people enjoyed music that didn’t take itself too seriously. Jones’s lively performance transformed it into a lighthearted anthem of 1920s optimism.

#8 “Charleston” by Arthur Gibbs and His Gang

Arthur Gibbs and His Gang’s “Charleston” captures the essence of 1920s dance culture with its infectious rhythm and upbeat tempo. Named after the famous dance of the era, this instrumental hit quickly became synonymous with the Jazz Age, encouraging listeners to embrace the decade’s free-spirited and celebratory atmosphere.

The song’s lively beat and syncopated rhythms made it ideal for the energetic Charleston dance, which dominated nightclubs and dance halls. “Charleston” represents the Roaring Twenties’ love of movement, rhythm, and rebellion against traditional norms. Gibbs’s playful arrangement embodies the joy of a new, carefree generation, creating a soundtrack for the bold self-expression that characterized the Jazz Age.

#9 “It Had to Be You” by Isham Jones Orchestra

Isham Jones Orchestra’s “It Had to Be You” is a romantic ballad that became one of the most enduring love songs of the 1920s. The song’s gentle melody and tender lyrics express a sense of destiny in love, resonating with audiences who found comfort and joy in its hopeful message.

The orchestration is warm and inviting, and the melody lingers, capturing the feeling of a timeless romance. “It Had to Be You” became a favorite for couples and remains a classic for its ability to convey both sentimentality and sincerity. The song reflects the era’s fascination with romance, making it an essential piece of 1920s music that has since become a standard in American pop culture.

#10 “California, Here I Come” by Al Jolson

Al Jolson’s “California, Here I Come” is a lively, optimistic song that captures the excitement of seeking new opportunities in the Golden State. With lyrics that celebrate California as a land of promise and adventure, the song resonated with those eager to escape the hardships of daily life and pursue their dreams.

The song’s infectious energy and Jolson’s enthusiastic performance made it an anthem for those captivated by the idea of prosperity and reinvention. “California, Here I Come” embodies the 1920s American Dream, reflecting the hope and ambition that characterized the decade. Jolson’s spirited delivery turned the song into a rallying cry for those daring to reach for a brighter future.

#11 “Sweet Georgia Brown” by Ben Bernie and His Orchestra

“Sweet Georgia Brown,” performed by Ben Bernie and His Orchestra, is a jazzy, toe-tapping tune that became an instant hit and remains a jazz standard. With its playful melody and lively beat, the song quickly became associated with the danceable, vibrant spirit of the Roaring Twenties, embodying the carefree atmosphere of the era.

The catchy refrain and joyful arrangement reflect the excitement of jazz music’s rise in popular culture, as “Sweet Georgia Brown” captured the fun and spontaneity of the time. Bernie’s orchestra infused the piece with charm and charisma, making it a favorite in dance halls. The song’s enduring appeal lies in its ability to bring the spirit of the Jazz Age to life, evoking a sense of joy and movement.

#12 “Dinah” by Ethel Waters

Ethel Waters’ “Dinah” is a soulful jazz tune that showcases her powerful vocals and ability to bring depth to every note. With a captivating melody and heartfelt lyrics, Waters sings of love and admiration, infusing the song with a warmth and sincerity that resonated deeply with audiences.

“Dinah” became one of the defining songs of the era, as Waters’ unique voice brought a richness and emotional nuance that made it unforgettable. The song reflects the Jazz Age’s appreciation for both romance and individuality, capturing the appeal of jazz as a personal, expressive genre. Waters’ performance transformed “Dinah” into a timeless piece that remains a classic in American jazz.

#13 “Baby Face” by Jan Garber and His Orchestra

Jan Garber and His Orchestra’s “Baby Face” is an upbeat, charming song that became a major hit in the 1920s, celebrating youthful love and the joy of companionship. The lyrics, which express adoration for a “baby face” that lights up the singer’s life, combined with the catchy melody, made it a favorite for couples and dancers alike.

The song’s playful energy reflects the carefree spirit of the decade, where love and lightheartedness took center stage. “Baby Face” became a staple of social gatherings, embodying the optimism and fun-loving nature of the Roaring Twenties. Garber’s arrangement adds a lively charm to the piece, making it an enduring classic that evokes the joy of young love.

#14 “Bye Bye Blackbird” by Gene Austin

Gene Austin’s “Bye Bye Blackbird” is a tender yet melancholic song that became popular for its relatable lyrics about longing and finding comfort in the familiar. Austin’s gentle voice and the song’s simple melody capture a bittersweet sentiment, as the singer bids farewell to loneliness and seeks solace in a place where he feels truly understood.

The song’s universal theme of searching for belonging resonated with audiences during a time of rapid change, as people sought both adventure and a sense of home. “Bye Bye Blackbird” became a classic of the decade, with its message of hope amid uncertainty. Austin’s heartfelt delivery made the song a comforting favorite, speaking to the emotions of those navigating the fast-paced world of the 1920s.

#15 “Blue Skies” by Ben Selvin and His Orchestra

Ben Selvin and His Orchestra’s “Blue Skies” is an optimistic tune that perfectly captures the carefree spirit of the 1920s. The song’s lyrics are filled with hope and joy, as it celebrates the brighter days ahead, reflecting the post-war optimism that defined the Jazz Age.

The lively melody and Selvin’s engaging orchestration brought a sense of warmth and happiness to audiences, making “Blue Skies” a popular choice in dance halls and radio broadcasts. Its message of resilience and positivity resonated deeply with listeners who embraced the Roaring Twenties’ outlook. The song remains an emblem of the era’s exuberance, bringing a touch of sunshine and joy to each performance.

#16 “My Blue Heaven” by Gene Austin

Gene Austin’s “My Blue Heaven” is a sweet, comforting ballad that became a massive hit in the 1920s, capturing the ideal of a peaceful, contented home life. Austin’s soft, tender voice brings warmth to the lyrics, which describe a serene domestic scene that offers an escape from the bustling world outside.

The song’s simple melody and heartfelt lyrics made it resonate with audiences who valued love and stability in a rapidly changing era. “My Blue Heaven” became a favorite for its sense of calm and reassurance, embodying a nostalgic ideal that many aspired to. Austin’s gentle performance helped make this song an enduring classic that reflects the hopes and dreams of the decade.

#17 “Stardust” by Hoagy Carmichael

Hoagy Carmichael’s “Stardust” is a beautiful, haunting tune that has become one of the most iconic jazz standards of all time. Written in 1927, the song’s romantic melody and poetic lyrics capture the longing and nostalgia that often accompany memories of a past love. Carmichael’s composition reflects the introspective side of the 1920s, offering a contrast to the high-energy dance numbers of the era.

The song’s elegance and timeless quality made it a favorite among jazz musicians and audiences alike, leading to countless renditions over the years. “Stardust” resonates as a dreamy exploration of love and loss, reflecting the Jazz Age’s depth and emotional complexity. Carmichael’s composition remains a cherished piece, celebrated for its beauty and sophistication.

#18 “Ol’ Man River” by Paul Robeson

Paul Robeson’s rendition of “Ol’ Man River” became an iconic piece of 1920s music, highlighting the struggles and resilience of African American communities. With his deep, resonant voice, Robeson brings gravity and emotion to the lyrics, which speak to the hardships of life and the enduring strength of those who persevere.

The song, composed by Jerome Kern and Oscar Hammerstein II for the musical Show Boat, captures the ongoing flow of the Mississippi River as a metaphor for life’s unyielding challenges. “Ol’ Man River” resonates with audiences for its raw honesty and powerful message, standing as a poignant reflection on struggle and hope. Robeson’s performance turned the song into an anthem of resilience and dignity.

#19 “Makin’ Whoopee!” by Eddie Cantor

Eddie Cantor’s “Makin’ Whoopee!” is a humorous, cheeky song that highlights the ups and downs of marriage in a playful and lighthearted way. With witty lyrics that explore the joys and challenges of newlywed life, Cantor’s performance brings a mischievous charm that captivated audiences looking for entertainment and laughter.

The song’s lively tempo and clever wordplay make it a quintessential piece of Jazz Age humor, reflecting the decade’s more open attitudes toward relationships and social conventions. “Makin’ Whoopee!” became popular for its fun, carefree approach to a serious subject, allowing listeners to laugh at the complexities of love. Cantor’s spirited rendition turned the song into a timeless classic with a delightful sense of mischief.

#20 “I Can’t Give You Anything But Love” by Cliff Edwards

Cliff Edwards’ rendition of “I Can’t Give You Anything But Love” is a tender, endearing song that captures the essence of unconditional affection, even in hard times. With its simple, heartfelt lyrics and gentle melody, the song tells the story of someone who, despite having little material wealth, offers love as the greatest gift they can give.

The song became an instant favorite for its sincerity and charm, resonating with audiences who understood the value of love over wealth. “I Can’t Give You Anything But Love” embodies the Jazz Age’s romanticism and celebration of true connection, making it a classic of 1920s music. Edwards’ warm performance brings authenticity to the piece, creating an enduring reminder of love’s power.

#21 “Ain’t Misbehavin'” by Fats Waller

Fats Waller’s “Ain’t Misbehavin’” is a lively, joyful tune that became a defining song of the 1920s jazz scene. With playful lyrics that express loyalty and devotion, Waller’s upbeat performance showcases his charisma and talent as both a pianist and singer, making the song an instant hit.

The song’s lighthearted, flirtatious tone perfectly encapsulates the carefree spirit of the Jazz Age, where people enjoyed new freedoms and social norms shifted. “Ain’t Misbehavin’” became a symbol of the fun and spontaneity that characterized the Roaring Twenties, as Waller’s engaging style brought charm and humor to the piece. His spirited rendition makes the song an enduring classic that continues to bring joy to listeners.

#22 “Singin’ in the Rain” by Cliff Edwards

Cliff Edwards’ “Singin’ in the Rain” became a cherished tune that captured the whimsical optimism of the Jazz Age. With its joyful lyrics about embracing life’s challenges with a smile, the song encourages listeners to face hard times with resilience and cheer, symbolizing the spirit of the 1920s.

Edwards’ warm, enthusiastic voice and the song’s catchy melody made it an anthem for positivity, fitting perfectly with the Roaring Twenties’ lively attitude. “Singin’ in the Rain” reminds us that joy can be found even in the rainiest days, creating a legacy of hope and resilience. Edwards’ lighthearted performance gives the song an enduring charm, making it a timeless classic that continues to uplift audiences.

#23 “Happy Days Are Here Again” by Leo Reisman and His Orchestra

“Happy Days Are Here Again” by Leo Reisman and His Orchestra became a celebrated anthem of the 1920s, symbolizing the optimism and excitement of the post-war years. With its upbeat melody and cheerful lyrics, the song captures the essence of joy and renewal, becoming an anthem for a generation ready to embrace better times.

The song’s lively rhythm and positive message resonated with listeners, making it a popular choice at parties and gatherings. “Happy Days Are Here Again” speaks to the Roaring Twenties’ embrace of freedom, adventure, and celebration. Reisman’s performance transformed the song into a cultural touchstone, providing a soundtrack for a decade focused on happiness and prosperity.

#24 “Am I Blue?” by Ethel Waters

Ethel Waters’ “Am I Blue?” is a soulful ballad that explores themes of heartache and longing, giving voice to the sadness that often lies beneath the surface of life’s celebrations. Waters’ powerful, emotive vocals bring depth and authenticity to the song, making it a favorite among audiences who connected with its raw emotion.

The song’s simple melody and heartfelt lyrics reflect a vulnerability that contrasts with the upbeat tunes of the Jazz Age, offering a more introspective take on love and loss. “Am I Blue?” resonates with listeners who understand the pain of unrequited love, making it an enduring piece of 1920s music. Waters’ soulful delivery transforms the song into a poignant reflection on love’s complexities.

#25 “St. Louis Blues” by Bessie Smith

Bessie Smith’s “St. Louis Blues” is a blues masterpiece that brings the soulful sound of the Mississippi Delta into the Jazz Age. Smith’s powerful voice and emotional depth convey the struggles and heartache that define the blues, making the song a powerful anthem of resilience and strength.

The song’s unique blend of jazz and blues elements set it apart, resonating with audiences who connected with its raw honesty and emotion. “St. Louis Blues” became a defining song of the 1920s, showcasing Smith’s talent and the power of the blues to tell profound stories. Her passionate performance captures the heart and soul of the era, making the song a timeless classic that transcends generations.

#26 “Black and Tan Fantasy” by Duke Ellington

Duke Ellington’s “Black and Tan Fantasy” is a haunting, intricate jazz composition that explores the complexities of race, identity, and struggle in the 1920s. With its rich blend of blues and jazz, the song captures the duality of joy and sorrow, using music to communicate a depth of emotion that resonated with diverse audiences.

The song’s unique instrumentation and Ellington’s skillful arrangements created a layered sound that brought sophistication to jazz, solidifying his reputation as a visionary in the genre. “Black and Tan Fantasy” reflects the tension and beauty of the Jazz Age, embracing themes of cultural expression and resilience. Ellington’s artistry transformed the piece into an enduring symbol of jazz’s power to tell complex, moving stories.

#27 “In the Jailhouse Now” by Jimmie Rodgers

Jimmie Rodgers’ “In the Jailhouse Now” is a playful, blues-inspired tune that tells the humorous story of a man’s misadventures and inevitable trouble with the law. With a catchy melody and Rodgers’ signature yodeling, the song became a hit, bringing a touch of humor and levity to the blues tradition.

The lyrics narrate the ups and downs of a carefree life, resonating with audiences who appreciated its witty take on life’s mishaps. “In the Jailhouse Now” captures the spirit of rebellion and individuality that defined the Jazz Age, with Rodgers’ charismatic performance adding charm to the story. The song’s clever lyrics and lighthearted style make it a timeless example of early country-blues fusion.

#28 “Crazy Blues” by Mamie Smith

Mamie Smith’s “Crazy Blues” is a groundbreaking song that became the first blues recording by an African American artist, sparking a nationwide blues craze. Smith’s powerful vocals and emotional delivery brought authenticity to the song, which tells the story of heartbreak and resilience, resonating deeply with listeners across the country.

The song’s success marked a turning point in music history, introducing blues to mainstream audiences and opening doors for future generations of African American artists. “Crazy Blues” captures the pain and strength of those navigating life’s struggles, reflecting the resilience and emotional depth that would define blues music. Smith’s pioneering performance transformed the song into a cultural milestone, setting the stage for the blues’ lasting influence.

#29 “The Prisoner’s Song” by Vernon Dalhart

Vernon Dalhart’s “The Prisoner’s Song” is a haunting ballad that tells the story of a man yearning for freedom and lost love, themes that resonated deeply with 1920s audiences. With a sorrowful melody and Dalhart’s expressive voice, the song captures the emotional weight of separation and the longing for a life once cherished.

As one of the first country music hits, “The Prisoner’s Song” introduced audiences to the genre’s storytelling style, blending folk and blues influences to create something uniquely American. The song’s universal themes of love, regret, and hope struck a chord across the nation, becoming one of the best-selling recordings of the decade. Dalhart’s performance helped cement country music as a defining voice in American music.

#30 “Rhapsody in Blue” by George Gershwin

George Gershwin’s “Rhapsody in Blue” is a groundbreaking composition that blends classical music with jazz, capturing the complexity and excitement of urban life in the 1920s. With its sweeping melodies and rhythmic energy, the piece paints a vivid picture of New York City’s bustling streets, a celebration of both elegance and modernity.

The composition’s unique fusion of genres helped elevate jazz as a sophisticated art form, making “Rhapsody in Blue” a cultural milestone. Gershwin’s work embodied the spirit of the Jazz Age, as audiences embraced the piece’s innovation and emotional depth. “Rhapsody in Blue” became synonymous with American ambition and creativity, a testament to Gershwin’s genius and the transformative power of jazz.

#31 “Dardanella” by Ben Selvin

Ben Selvin’s “Dardanella” is a jazz-influenced dance tune that quickly captivated the nation, becoming one of the best-selling songs of the 1920s. With its catchy rhythm and upbeat melody, “Dardanella” embodied the excitement and energy of the Jazz Age, encouraging people to dance and embrace the new, fast-paced social scene of the decade.

The song’s instrumental arrangement highlighted the appeal of jazz music in both formal and social settings, making it popular across a wide audience. “Dardanella” reflects the carefree spirit of the 1920s, as people sought joy and entertainment during a time of economic growth and cultural change. Selvin’s lively interpretation made it a defining hit, capturing the heart and soul of the Roaring Twenties.

Frequently Asked Questions

What themes are common in songs from the 1920s?

Songs from the 1920s often explore themes of joy, romance, freedom, and resilience. Many tracks also capture the excitement of modernity and the cultural shifts of the Jazz Age.

Why were jazz and blues so popular in 1920s music?

Jazz and blues provided fresh, expressive sounds that embodied the decade’s spirit of liberation and change. These genres allowed for improvisation and emotional depth, resonating deeply with audiences of the time.

How did songs from the 1920s reflect social changes of the era?

1920s music mirrored the era’s break from tradition, with upbeat rhythms and lyrics celebrating newfound freedoms, urban life, and the Roaring Twenties’ modern ideals. These songs often embraced themes of rebellion and carefree living.

Are songs from the 1920s still influential today?

Yes, songs from the 1920s continue to influence modern jazz, blues, and pop music. Their timeless melodies and innovative styles have left a lasting impact on contemporary artists and listeners alike.