30 Best 1920s Songs for a Roarin’ Good Time

The 1920s was a deeply transformative time for music. Not only were listeners able to play early models of records on phonographs thanks to Victor records, but the new commercial availability of music gave rise to new hit genres like jazz and country.

Below is a comprehensive overview of some of the best 1920s songs featuring the most popular and revolutionary artists, including jazz greats like Louis Armstrong and blues icons like Ma Rainey.

West End Blues – Louis Armstrong

Trumpeter Louis Armstrong blazed a trail for fellow jazz musicians by releasing some of the “swing” era’s most significant recordings. His revolutionary tune ‘West End Blues,’ written by his friend and mentor Joe Oliver, brought jazz music into the mainstream limelight. Though the song was written in standard 12-bar blues form, Armstrong’s dynamic trumpet solo in the first minute blends jazzy musical scales with traditional blues rhythm.

Related: songs with a trumpet, jazz legends

Rhapsody in Blue – Paul Whiteman and George Gershwin

In the early 1920s, jazz music was largely considered to be inappropriate and subpar to other popular genres. Composers Paul Whiteman and George Gershwin wanted to change that. Performed at one of Whiteman’s concertos, Gershwin’s renegade ‘Rhapsody in Blue’ set a new tone for the swinging genre. According to author Paul Osgood, one of jazz’s distinguished writers, with Whiteman’s legendary concert, he “made an honest woman out of jazz.”

In the Jailhouse Now – Jimmie Rodgers and Webb Pierce

Vaudeville music was still widely popular in the 1920s after gaining widespread attention in the 1890s. Jimmie Rodgers’ and Webb Pierce’s ‘In the Jailhouse Now’ was a well-received vaudeville tune released in 1928. The comedic, entertaining story follows a petty thief who inadvertently gets locked up in the slammer.

Related: Does crime pay? Find out with the best songs about crimes.

Ain’t Misbehavin’ – Fats Waller

Though jazz songwriter Fats Waller wrote ‘Ain’t Misbehavin” in about five minutes with fellow writers, the highly successful 1929 number would also have several cover versions. Originally composed for an off-Broadway show, other in-demand musicians such as Louis Armstrong, Ella Fitzgerald, and Nat King Cole put their artistic stamp on their own renditions, as well.

Charleston – Arthur Gibbs

Accompanying the jazz age was the beloved new dance, “the Charleston.” Instrumentalist Arthur Gibbs and his band, “His Gang,” released the original song to accompany the now-infamous dance in 1923. The instrumental became instantly popular. It went straight to number one on the charts.

Swanee – Al Jolson

Named after a Stephen Foster tune that mentions the lazy southern river, “the Suwanee,” Al Jolson wrote about languid, nature-filled southern states with his tune ‘Swanee.’ The song mentions southern words like “dixie” and “mammy,” which became a huge hit in southern America. However, writers George Gershwin and Irving Caesar both hailed from the north.

Prisoner’s Song – Vernon Dalhart

Johnny Cash would have loved this jail-themed song written by Dalhart and his fellow family members. The song follows the forlorn story of a prisoner missing his lover while transported to different jail cells. This was a monumental country song in the ’20s because it was the genre’s first commercial hit. ‘Prisoner’s Song’ kicked off the country genre’s rise to mainstream success.

Related: Check out the best songs about jail.

Ol’ Man River – Paul Robeson

Mississippian song ‘Ol’ Man River’ was adapted to musical form by Jerome Kern and Oscar Hammerstein II, with the story first appearing in the Edna Ferber novel Show Boat. Kern and Hammerstein both had baritone Paul Robeson in mind as they adapted the story. Robeson eventually recorded the tune with Paul Whiteman’s band backing him. The song chronicles the story of musicians on the delta who travel by boat to perform for remote towns.

Related: This song features on our list of songs about rivers.

Black and Tan Fantasy – Duke Ellington

The original recording of Duke Ellington’s ‘Black and Tan Fantasy’ is a part of the Grammy Hall of Fame. Ellington’s sophisticated compositions helped break down barriers for fellow African-Americans. His songs, which sometimes centered around African culture, were game-changing, making room for minority artists to be viewed as respected musicians instead of just entertaining support acts. If you liked this, see our pick of Duke Ellington’s most famous songs.

Related: Get inspired with our playlist of equality songs.

Crazy Blues – Mamie Smith

Singer Mamie Smith changed blues music forever with her hit song ‘Crazy Blues.’ In a male-dominated field, she proved women with powerful voices could spark record sales too. She did just that with this empowering tune about an abused woman who takes fate into her own hands. During the first month of its release, Smith’s impassioned recording sold over 75,000 units.

Related: Feel courageous with the best female empowerment songs.

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

Singer and actor Bing Crosby recorded a notable version of Cole Porter’s ‘Let’s Do It (Let’s Fall in Love)’ in 1929. Originally written by Porter for his successful musical Paris, this vintage track could be considered a “pop” song by today’s standards. Its legacy is steeped in controversy. One quick listen to the lyrics, and you realize this is one of the earliest songs to cover recreational, intimate relationships in detail openly.

Related: Enjoy the best Broadway songs of all time. No tickets are necessary!

Dardanella – Ben Selvin

The instrumental number ‘Dardanella’ became one of Ben Slevin’s biggest hits and one of the 1920s most favored songs. Heavy with a flowing bass line, the easily recognizable tune was the first to garner over 5 million copies sold. With numbers like that, it came to be recognized as “the biggest hit of 1920.”

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

Band leader Ace Brigode’s most popular tune, ‘Yes Sir That’s My Baby,’ is a 1925 classic. By the mid-1920s, Brigode had increased his “Ten Virginians” band to “Fourteen Virginians.” Brigode’s high band member count allowed a full orchestra to back his danceable tunes.

Related: Who’s your “baby?” Send them these songs with the word baby in them.

My Blue Heaven – Gene Austin

Written while on the early 1900’s preeminent label, Victor Records, ‘My Blue Heaven’ was quickly penned by Walter Donaldson and George A. Whiting while waiting to play a game of pool. The tune would become a huge hit for the Victor studio, with 5 million copies sold worldwide.

Related: Listen to our playlist of the best going to heaven songs.

Makin’ Whoopee – Eddie Cantor

A cautionary tale about the troubles married life can bring, ‘Makin’ Whoopee’ was written by popular 1920s composer Walter Donaldson. Eddie Cantor’s version became a huge hit, and the tune had staying power. It has been included in both recorded and live forms in several movies, including Sleepless in Seattle and The Fabulous Baker Boys.

Related: Love isn’t always a walk in the park. Listen to our stay together songs playlist when you need some strength.

Heebie Jeebies – Ethel Waters

Ethel Waters and Her Jazz Band first recorded this jazz classic in 1926. When Louis Armstrong decided to cover it, he once again revolutionized the genre on the fly. During his recording session, he dropped the paper with the ‘Heebie Jeebies’ lyrics on it. Not wanting to lose momentum, he improvised for the rest of the track. This gave rise to the “scat” technique heard in many jazz songs after Armstrong’s release.

Honey – Rudy Vallée

While ‘Honey’ was a 1929 hit, the song endured for decades. Written by the songwriting trio of Seymour Simons, Haven Gillespie, and Richard A. Whiting, musician Rudy Vallee released the tune with his band, the Connecticut Yankees. ‘Honey’ would go on to be covered many times, and in 1945 it was featured in the film ‘Her Highness and the Bell Boy.’

Related: Our list of the best sweet songs is kind of like a candy shop for the ears!

Ain’t We Got Fun – Van and Schenck

Composer Richard A. Whiting was the source of many 1920s hits, including the “foxtrot” number ‘Ain’t We Got Fun.’ Van and Schenck were the first to record it in 1921. The song’s lyrics would become widely referenced in pop culture. Writer F. Scott Fitzgerald mentions the tune in his book The Great Gatsby. The song’s lyric, “The rich get richer, and the poor get poorer,” became a popular one-liner to recite when talking about class struggle.

Sweet Georgia Brown – Ben Bernie

This jazz-pop hit was composed by musician Ben Bernie after an inspiring conversation with a Georgia State House of Representatives member, Dr. George Thaddeus Brown. Just before Brown’s daughter was born, a Georgia assembly declared she should be named after their great state. Thus, Brown and his wife named their baby girl Georgia. After the interesting conversation, Bernie penned ‘Sweet Georgia Brown.’

Related: Take a trip with the best songs about US states.

It Had to Be You – Gus Kahn and Isham Jones

Multi-instrumentalist Isham Jones and his big band wrote ‘It Had to Be You’ with lyricist Gus Khan. The number one hit is a romantic declaration of love and admiration from one lover to another who has finally found “the one.”

Related: Have you found your true love? Check out the best songs about someone special.

Louise – Maurice Chevalier

Songwriter Richard Whiting was a busy man in the ’20s, writing many hit songs for the decade’s biggest artists. For his tune ‘Louise,’ he paired up with writer Leo Robin. They wrote the song for a 1929 movie, Innocents of Paris. For the film, they hired Maurice Chevalier to perform the song.

Some of These Days – Sophie Tucker

This early pop song was first recorded in 1910. However, it proved to have “hit potential,” and it became known as Sophie Tucker’s “signature song.” She would go on to record several versions, and quite a few were featured in movies like Lights of New York in 1928. Tucker also made an appearance as a singer at a nightclub in the 1929 film Honky Tonk and performed the song live while in character.

Always – Vincent Lopez

Jazz standard ‘Always’ was written in the mid-1920s by popular songwriter Irving Berlin as a love song dedicated to his soon-to-be wife. The hit would go on to be widely covered by artists like Patsy Cline and used in cinematic projects like The Pride of the Yankees, which documents the life of baseballer Lou Gehrig. ‘Always’ features unique piano melodies containing only notes of the black keys being played.

Valencia – Franklyn Baur and Paul Whiteman

Paul Whiteman scored yet another number-one hit with ‘Valencia.’ Featuring an enthusiastic vocal performance by Franklyn Baur, the song takes on a more pop flavor than jazz or Spanish-style music. After its release, it went on to become the most popular hit of 1926.

Blue Yodel (T for Texas) – Jimmie Rodgers

An early pioneer of country music, which first saw commercial success in the 1920s, Jimmie Rodgers was instrumental in the genre’s rise to popularity. Often coined as “the father of country music,” many of his early releases, including ‘Blue Yodel (T for Texas)’ were a mix of blues progressions, country melodies, and Rodgers’ signature yodeling vocal technique. This never-before-heard approach would go on to be attributed to Rodgers and known as “Blue Yodels.”

Related: See our playlist of old time country music.

Pinetop’s Boogie Woogie – Pinetop Smith

In 1928, Pinetop Smith released a rollicking song called ‘Pinetop’s Boogie Woogie.’ The genre-defying track would ultimately create its own genre, boogie-woogie, a piano-driven bouncing form of ragtime. This early genre would later transform into modern-day rock and roll.

Related: Check out the genre this song inspired on our list of rock and roll songs.

Down Hearted Blues – Bessie Smith

“Gee, but it’s hard to love someone when that someone don’t love you.” Originally written by Lovie Austin and Alberta Hunter, Hunter sang ‘Down Hearted Blues’ with Joe Oliver’s band in Chicago while performing a string of dates at the Dreamland Cafe. But Bessie Smith’s raw, relatable vocal performance of the tune would become the most popular among listeners. Released as her debut single, the tune sold 780,000 copies during its first few months on the market.

Related: Feeling down? Here are some good blues songs.

See See Rider Blues – Ma Rainey

First written and released in 1924 by “the mother of the blues” singer Ma Rainey, ‘See See Rider Blues’ is a story about an unfaithful boyfriend who mooches off his lovers. Rock n’ roll sensation Elvis Presley would record a popular version of the tune for his live album On Stage in 1970.

Statesboro Blues – Blind Willie McTell

Hailing from Georgia, blues musician Blind Willie McTell wrote ‘Statesboro Blues’ after one of the state’s small towns. An early star of “the Piedmont Blues” style, his rolling fingerstyle rhythm performed on a 12-string guitar became a signature sound for the subgenre.

Matchbox Blues – Blind Lemon Jefferson

“Sittin’ here wonderin’ will a matchbox hold my clothes.” This introductory lyric to Blind Lemon Jefferson’s ‘Matchbox Blues’ refers to falling on financial hard times, giving way to a deeper blues story of a man who’s down on his luck. Rock group The Beatles would go on to cover ‘Matchbox Blues’ and several other blues hits. Their popular version contains a lyrical error in regard to the aforementioned line. In the Beatles’ version, Ringo sings, “Sittin’ here watchin’, matchbox hole in my clothes.”

Related: Short on cash? Here’s a playlist of songs about being broke.

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About Ged Richardson

Ged Richardson is the Founder and Editor-in-Chief of ZingInstruments.com. He has been featured in Entrepreneur, PremierGuitar, Hallmark, Wanderlust, CreativeLive, and other major publications. As an avid music fan, he spends his time researching and writing about new and old music, as well as testing and reviewing music-related products. He's played guitar in various bands, from rock to gypsy jazz. Be sure to check out his YouTube channel, where he geeks out about his favorite bands.

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