30 Best 1920s Songs for a Roarin’ Good Time

The 1920s, also known as the “Roaring Twenties,” were a time of dramatic social and cultural change in the United States. This decade saw the rise of jazz music, flapper fashion, and the prohibition era, which gave rise to illegal speakeasies and bootlegging.

Music played a significant role in shaping the culture of the 1920s, with jazz and blues becoming hugely popular among young people. Many of the songs from this era reflected the exuberance and excitement of the times, while others spoke to the social and political issues of the day.

In this article, we’ll take a look at some of the most popular songs from the 1920s, exploring the stories behind the music and the cultural context that made them so significant. From jazz standards to blues ballads, these songs are a testament to the enduring legacy of the Roaring Twenties, and the ways in which music can capture the spirit of a moment in time.

1. West End Blues – Louis Armstrong

“West End Blues” is a jazz standard performed by Louis Armstrong and his Hot Five in 1928. The song begins with a trumpet solo by Armstrong, which is considered one of the greatest in jazz history. The melody is simple and bluesy, but Armstrong’s virtuosity and improvisation take it to another level. The song also features Earl Hines on piano and a rhythm section that swings hard. “West End Blues” was a significant influence on the development of jazz, and its impact can still be heard in contemporary jazz and popular music.

2. Rhapsody in Blue – Paul Whiteman and George

“Rhapsody in Blue” is a musical composition by George Gershwin, performed here by Paul Whiteman and his orchestra with Gershwin on piano. The piece blends elements of jazz and classical music, creating a uniquely American sound. The opening clarinet solo, famously known as the “wail”, sets the tone for the entire piece. “Rhapsody in Blue” is a groundbreaking work that captured the spirit of the Roaring Twenties and became one of Gershwin’s most beloved compositions. Its influence can be heard in a wide range of musical genres, from film scores to pop music.

3. In the Jailhouse Now – Jimmie Rodgers and Webb Pierce

“In the Jailhouse Now” is a country-blues song performed by Jimmie Rodgers and Webb Pierce. The song tells the story of a man who finds himself in jail after getting involved in various illegal activities, but who maintains a positive attitude throughout his incarceration. The song features Rodgers’ distinctive yodeling, which became his trademark, and Pierce’s smooth vocals. “In the Jailhouse Now” was a commercial success for both artists and became a popular song in the country and blues genres. Its influence can still be heard in contemporary country and Americana music.

4. Ain’t Misbehavin’ – Fats Waller

“Ain’t Misbehavin'” is a jazz standard composed by Fats Waller, performed here by the composer himself. The song is a lighthearted ode to living life to the fullest and not worrying about societal norms or expectations. Waller’s piano playing and playful vocals give the song a lively, upbeat feel. “Ain’t Misbehavin'” became a popular song during the swing era and has since become a jazz standard, covered by countless artists in a variety of genres. Its catchy melody and joyful lyrics continue to be celebrated and enjoyed today.

5. Charleston – Arthur Gibbs

“Charleston” is a jazz song composed by James P. Johnson, with lyrics by Cecil Mack. It was first featured in the 1923 Broadway musical “Runnin’ Wild,” which helped popularize the dance style of the same name. The song features a catchy melody, fast tempo, and syncopated rhythms that are characteristic of the Charleston dance. The version presented here, performed by Arthur Gibbs and his Gang, showcases the lively energy and upbeat spirit of the tune. “Charleston” became a hit during the 1920s and remains a beloved piece of jazz history, synonymous with the exuberant spirit of the Roaring Twenties.

6. Swanee – Al Jolson

“Swanee” is a song composed by George Gershwin, with lyrics by Irving Caesar. It was originally written for the Broadway revue “Demimonde” in 1919 but gained fame when Al Jolson performed it in the musical “Sinbad” in 1920. Jolson’s rendition became a sensation and helped launch Gershwin’s career. The song features a lively melody and a catchy chorus that Jolson delivers with his signature style. The version presented here showcases Jolson’s dynamic vocal range and the jaunty accompaniment by the Victor Orchestra. “Swanee” remains a beloved classic of the 1920s and a testament to the enduring power of American popular music.

7. Prisoner’s Song – Vernon Dalhart

“Prisoner’s Song” is a country blues song originally recorded by Vernon Dalhart in 1924. The song tells the story of a prisoner lamenting his imprisonment and separation from his loved ones. It features a simple, repetitive melody with sparse accompaniment that accentuates the somber lyrics. Dalhart’s recording of the song was a massive commercial success and is credited with helping to popularize country music in the United States. The song has since been covered by numerous artists and has become a standard in the country and blues repertoire. The version presented here showcases Dalhart’s plaintive vocals and the understated instrumentation that has become synonymous with the song.

8. Ol’ Man River – Paul Robeson

“Ol’ Man River” is a song from the musical “Show Boat” composed by Jerome Kern and written by Oscar Hammerstein II. It was first performed by Paul Robeson in the original 1927 Broadway production and has since become one of his signature songs. The song is a powerful meditation on the struggles of African American laborers working on the Mississippi River, with lyrics that address issues of oppression, exploitation, and resilience. Robeson’s deep, resonant voice and emotive delivery bring the song to life, conveying both the pain and the strength of the characters it portrays. The song has since become a classic of American musical theater and an enduring symbol of the African American experience.

9. Black and Tan Fantasy – Duke Ellington

“Black and Tan Fantasy” is a classic jazz composition by Duke Ellington and his frequent collaborator, Bubber Miley. The piece, which was recorded in 1927, is notable for its moody, evocative melody and its inventive use of orchestration, including muted trumpets and clarinets. The song’s title refers to the Black and Tan Club, a popular nightclub in Harlem during the 1920s. Ellington’s arrangement captures the ambiance of the club, with its dimly lit interiors and sultry atmosphere. “Black and Tan Fantasy” is now considered a jazz standard and has been covered by many other musicians over the years.

10. Crazy Blues – Mamie Smith

“Crazy Blues” is a historic blues song recorded by Mamie Smith in 1920, becoming the first blues record by a black female artist. The song is a mournful lament of a woman who has been abandoned by her lover, with Smith’s soulful voice conveying the pain and heartbreak. “Crazy Blues” was a commercial success, selling over a million copies, and marked the beginning of the era of the “race records” market, catering to African American audiences. The song is considered a landmark in blues music, opening the door for other black female artists and influencing the development of jazz and rhythm and blues.

11. Let’s Do It (Let’s Fall in Love) – Bing Crosby and The Dorsey Brothers

“Let’s Do It (Let’s Fall in Love)” is a classic jazz standard originally recorded by Cole Porter in 1928, and later popularized by Bing Crosby and The Dorsey Brothers in 1936. The song features playful and witty lyrics that explore the concept of love and attraction among various animals, insects, and even mythical creatures. The lively melody is characterized by a swinging rhythm, catchy chorus, and scat singing, which was a popular vocal improvisation technique at the time. The song’s enduring popularity has made it a timeless classic, and it continues to be covered and performed by musicians across different genres and eras.

12. Dardanella – Ben Selvin

“Dardanella” is a popular song from the early 20th century that was originally composed for a musical comedy. Ben Selvin and His Orchestra’s 1919 recording of the song became a major hit and is widely considered the first million-selling record in history. The song’s melody features a prominent banjo riff and a catchy chorus that’s easy to sing along to. Its upbeat, lighthearted tone was popular during the Roaring Twenties, and it remains a classic example of early jazz music. The song has since been covered by many artists and has become a standard in the jazz repertoire.

13. Yes Sir That’s My Baby – Ace Brigode and His Fourteen Virginians

“Yes Sir, That’s My Baby” is a popular song originally written in 1925, with music by Walter Donaldson and lyrics by Gus Kahn. It was recorded by Ace Brigode and His Fourteen Virginians in the same year and became an instant hit, inspiring many other versions by different artists. The song’s catchy melody and playful lyrics, such as “Who’s your daddy? Yes, indeed!” and “Yes, sir, that’s my baby, no sir, don’t mean maybe,” have made it a timeless classic of the jazz and swing era. The upbeat tempo and spirited vocals of Ace Brigode and his band make this a fun and lively tune to listen to.

14. My Blue Heaven – Gene Austin

“My Blue Heaven” is a classic ballad performed by Gene Austin that was released in 1928. The song features Austin’s smooth crooning voice and a slow, romantic melody that captures the nostalgic feelings of a bygone era. The lyrics express the singer’s joy and contentment in finding true love, describing a peaceful and idyllic life with his partner. The song’s simple yet heartfelt message resonates with listeners of all ages, making it a timeless classic. With its catchy tune and memorable lyrics, “My Blue Heaven” has become a beloved standard in the Great American Songbook and a must-have in any music lover’s collection.

15. Makin’ Whoopee – Eddie Cantor

“Makin’ Whoopee” is a humorous jazz and pop standard from the 1920s, sung by Eddie Cantor. The song is a tongue-in-cheek commentary on the institution of marriage and the domesticity that comes with it. Cantor’s delivery is playful and witty, his voice moving easily from high to low notes as he sings of the trials and tribulations of being married. The song’s clever lyrics and catchy melody have made it a classic, with its depiction of the ups and downs of married life resonating with audiences for decades. Its enduring popularity has ensured its place in the Great American Songbook.

16. Heebie Jeebies – Ethel Waters

“Heebie Jeebies” is a classic blues song originally recorded by Ethel Waters in 1926. It features a syncopated melody and a lively tempo that showcases Waters’ distinctive vocal style. The song’s lyrics convey a sense of anxiety and unease, describing a feeling of being “jittery” and “nervous.” Despite its somewhat ominous tone, the song is also infused with a sense of joy and excitement, capturing the spirit of the roaring ’20s. “Heebie Jeebies” is an enduring example of early blues music and a testament to Waters’ immense talent as a singer and performer.

17. Honey – Rudy Vallée

“Honey” is a romantic ballad performed by Rudy Vallée in 1929 that became a popular hit during the early 1930s. The song is characterized by Vallée’s smooth crooning and the use of a megaphone to amplify his voice, a technique that he pioneered. The lyrics are sentimental and nostalgic, with the singer expressing his love for his significant other and longing for her presence. The melody is catchy and easy to sing along to, making it a popular choice for cover versions by other artists. “Honey” remains a classic example of the romantic ballads that were popular during the early days of the Great Depression.

18. Ain’t We Got Fun – Van and Schenck

“Ain’t We Got Fun” is a cheerful song with lyrics that describe a couple enjoying life despite their financial struggles during the Roaring Twenties. The upbeat melody, punctuated by the iconic kazoo sound, makes it a popular tune for nostalgic sing-alongs. Originally composed in 1920, the song’s catchy tune and relatable lyrics helped it become an instant hit. Its popularity continued to grow throughout the decade, and it has been covered by numerous artists over the years. “Ain’t We Got Fun” captures the optimism and carefree spirit of the 1920s and remains a beloved classic of the era.

19. Sweet Georgia Brown – Ben Bernie

“Sweet Georgia Brown” is a classic jazz standard originally recorded by Ben Bernie and his orchestra in 1925. The song features a lively and upbeat melody, with catchy lyrics that celebrate the charms of a Southern belle. It has since become a popular tune for jazz bands and musicians to cover, with countless renditions recorded over the years. The song’s popularity was cemented by its use as the theme song for the Harlem Globetrotters basketball team. With its energetic tempo and memorable melody, “Sweet Georgia Brown” is a timeless classic of the jazz genre.

20. It Had to Be You – Gus Kahn and Isham Jones

“It Had to Be You” is a classic love song written by Gus Kahn and Isham Jones in 1924. The song has been covered by many artists over the years and is considered a timeless classic. The melody is sweet and romantic, and the lyrics express the feeling of falling in love and being unable to resist the attraction to someone. The song has been featured in several movies and TV shows and has become a standard at weddings and romantic events. The song’s popularity has endured for nearly a century, and its timeless quality continues to capture the hearts of music lovers around the world.

21. Louise – Maurice Chevalier


“Louise” is a French-American song originally recorded by Maurice Chevalier in 1929. The song is about a man expressing his love for his sweetheart named Louise. The upbeat melody, coupled with Chevalier’s charming vocals, create a cheerful and lively atmosphere. The song was a commercial success, topping the charts in France and becoming a popular hit in the United States as well. With its catchy tune and romantic lyrics, “Louise” became a classic of the early 20th century and has been covered by many artists in various languages over the years.

22. Some of These Days – Sophie Tucker

“Some of These Days” is a popular song from the early 20th century that was made famous by the vaudeville performer Sophie Tucker. The song features upbeat jazz rhythms and Tucker’s powerful vocals, making it a classic example of early jazz and blues music. The lyrics describe a woman’s anticipation of her lover’s return after a period of separation, with the chorus proclaiming “Some of these days, you’re gonna miss me honey / Some of these days, you’re gonna feel so lonely.” The song has since been covered by numerous artists and remains a staple of the jazz and blues canon.

23. Always – Vincent Lopez

“Always” is a classic romantic ballad written by Irving Berlin and performed by Vincent Lopez. The song features a slow and dreamy melody with smooth vocals and lush orchestration. The lyrics speak of a timeless love that endures through life’s trials and tribulations, promising to always be there for the one you love. With its sentimental tone and timeless message, “Always” has become a beloved classic and has been covered by many artists over the years. It’s a song that reminds us of the power of love and the enduring nature of true romance.

24. Valencia – Franklyn Baur and Paul Whiteman

“Valencia” is a romantic ballad that was popularized by Franklyn Baur and Paul Whiteman in the 1920s. The song has a Spanish flair and tells the story of a man who falls in love with a beautiful woman from the city of Valencia. The melody is upbeat and catchy, and the lyrics speak of the passion and desire the protagonist feels for his love interest. The song was one of the biggest hits of the decade and has been covered by numerous artists since its release. “Valencia” captures the essence of the romantic music of the era and remains a beloved classic to this day.

25. Blue Yodel (T for Texas) – Jimmie Rodgers

“Blue Yodel (T for Texas)” is a classic country blues song performed by Jimmie Rodgers in 1927. The song is a lament about a lost love, with Rodgers using his signature yodeling technique to add an emotional depth to the lyrics. The song’s catchy melody and simple chord progression, along with Rodgers’ unique vocal style, made it an instant hit and cemented his status as the “Father of Country Music”. “Blue Yodel (T for Texas)” has been covered by numerous artists over the years and is still considered a country music classic.

26. Pinetop’s Boogie Woogie – Pinetop Smith

“Pinetop’s Boogie Woogie” is a classic boogie-woogie piano instrumental, recorded by Pinetop Smith in 1928. The song features a driving bassline, a lively melody, and infectious rhythm, creating a lively and energetic sound that became a hallmark of the genre. The song was a massive hit and helped popularize boogie-woogie music in the United States. Pinetop’s fast and rhythmic playing style inspired numerous pianists, and the song has since been covered by many artists. Despite Pinetop Smith’s tragic death at a young age, “Pinetop’s Boogie Woogie” remains a timeless classic of early blues and boogie-woogie music.

27. Down Hearted Blues – Bessie Smith

“Down Hearted Blues” is a classic blues song recorded by Bessie Smith in 1923, considered to be one of her signature tunes. The song features Smith’s powerful and soulful vocals, accompanied by a band with a prominent trombone and piano. The lyrics speak of the pain and sorrow of a broken heart, and Smith’s emotive delivery captures the raw emotions of heartbreak. The song was hugely popular at the time of its release, and helped establish Smith as one of the leading voices in blues music. Its enduring popularity has cemented it as a blues standard and a landmark recording in American music history.

28. See See Rider Blues – Ma Rainey


“See See Rider Blues” is a classic blues song recorded by “Mother of the Blues” Ma Rainey in 1924. The song features a simple, catchy melody and lyrics that reflect the pain and hardship of the African American experience in the early 20th century. The lyrics tell the story of a woman who has been abandoned by her lover and left to suffer on her own. Rainey’s powerful and soulful voice conveys the emotion of the song, and her performance helped to establish her as one of the most important figures in blues music. The song has since been covered by numerous artists and is considered a blues standard.

29. Statesboro Blues – Blind Willie McTell

“Statesboro Blues” is a classic blues song that was popularized by Blind Willie McTell in 1928. The song has been covered by various artists and has become a staple in the blues repertoire. The song features McTell’s signature fingerpicking style on the guitar and his distinctive vocal delivery. The lyrics tell the story of a man who has been traveling and is now down on his luck in Statesboro, Georgia. The song’s melancholic tone and haunting melody capture the essence of the blues and have made it a timeless classic in the genre.

30. Matchbox Blues – Blind Lemon Jefferson

“Matchbox Blues” is a classic blues song performed by Blind Lemon Jefferson. The song features Jefferson’s distinctive finger-picking guitar style and his soulful, expressive vocals. With its catchy melody and memorable lyrics, “Matchbox Blues” is a timeless example of the country blues genre. The song tells the story of a man who has lost everything, including his home, his money, and his woman. Despite his troubles, the man keeps his sense of humor and optimism, singing “I’m gonna find me a matchbox, baby, and cook my supper in the dark.” The song’s simple yet powerful message of resilience and determination has resonated with generations of music lovers.

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