25 Popular Songs From The 1920s

The 1920s often get overlooked when it comes to music. But songs from the 1920s were a combination of styles, from jazz and blues to classical. As a result, many popular songs of the 1920s remain well-known, and many of those we forget deserve remembering.

Here are some of the most popular songs of the 1920s.

“Rhapsody in Blue” by George Gershwin

Year:1924

Paul Whitman commissioned ‘Rhapsody in Blue' from George Gershwin. Musically it's a fascinating piece because Gershwin blends the conventions of classical music theory with nascent jazz.

Audiences loved it, but critics were ambivalent. Despite this, ‘Rhapsody in Blue' cemented Gershwin in musical history and became the soundtrack for the developing Jazz Age.

“Ain't Misbehavin'” by Fats Waller

Year: 1929

‘Ain't Misbehavin” sounds as cheeky and playful as the title suggests. In Fats Waller's hands, it comes alive with daring improvisations and harmonies.

Waller debuted his composition in Harlem for an all-black revue called ‘Hot Chocolate.' Originally Margaret Simms and Paul Bass sang the piece, but it also became an instrumental staple. Famously, Louis Armstrong turned it into an unforgettable trumpet solo.

“Ol' Man River” by Paul Whiteman

Year: 1928

‘Ol' Man River' began life as a musical number in ‘Showboat.' Jerome Kern wrote the music, and Oscar Hammerstein wrote the lyrics.

‘Ol' Man River' is memorable for its ponderous bass opening. As sung by Paul Whiteman, it has the richness and smoothness of dark chocolate.

Later, Kern's music contrasts this legato verse with a sprightly banjo, the beloved instrument of the 1920s.

As you listen, pay attention to the lyrics. ‘Showboat' proved musicals could have serious subjects. The sentiment comes through in the music, and ‘Ol Man River' is no exception.

“Bye Bye Blackbird” by Gene Austin

Year: 1926

The first thing you notice listening to Gene Austin's famous version of ‘Bye Bye Blackbird' is that it begins with an introduction that often gets omitted in modern recordings.

The song was composed by Ray Henderson, and the lyrics are by Mort Dixon.

Not only was ‘Bye Bye Blackbird' one of the most popular songs of the 1920s, but it became a cultural touchstone. Listeners will recognize it from films and television series like:

• Tenko
• Peaky Blinders
• The History Boys

“Charleston” by Arthur Gibbs

Year: 1923

Another of the most memorable songs from the 1920s is ‘Charleston.' It first appeared in the Broadway musical ‘Running Wild.' Cecil Mack wrote the words, and James P Johnson set them to music, inspired by the stride piano approach to jazz.

In this fusion of jazz and ragtime, the left-hand plays a ragtime rhythm and feel while the right hand improvises a melody.

“Sweet Georgia Brown” by Ben Bernie 

Year:1925

According to Ben Bernie, his inspiration for the jazz standard ‘Sweet Georgia Brown' came from a meeting with George Thaddeus Brown, who explained that he named his daughter Georgia for the state she was born in.

Bernie cited this anecdote as the source of both music and lyrics, despite the song's words being attributed to Maceo Pinkard.

Its popularity remains ongoing, and jazz artists still cover ‘Sweet Georgia Brown' when they want to reinvent the musical wheel.

“In the Jailhouse Now” by Jimmie Rodgers

Year:1928

‘In The Jailhouse Now' has a long and colorful history as a vaudeville act. It became a popular song in the 1920s thanks to Jimmie Rodgers, who sang it while playing the banjo.

The other distinctive quality of Rodgers' rendition of ‘In the Jailhouse Now' is his signature yodel.

The Soggy Bottom Brothers immortalized ‘In The Jailhouse Now' for posterity when they sang it in ‘O Brother, Where Art Thou?'

“Dark Was the Night” by Blind Willie Johnson

Year:1927

What's immediately noticeable about ‘Dark Was the Night' is its use of slide guitar instead of the popular banjo.

‘Dark Was the Night' takes its name from a hymn. And while Johnson sang and played at street corners or in mission halls, this blues-gospel hybrid is primarily instrumental. The most vocalization it has is Johnson's close-mouthed humming on the melody line.

“Swanee” by Al Jolson

Year: 1920

When it comes to songs of the 1920s, it's impossible not to talk about ‘Swanee.' George Gershwin wrote it in 1919, and when Al Jolson sang it in 1920, it quickly became one of the most popular songs of the 1920s.

Suddenly everyone knew about ‘Swanee.' One of the most distinctive features is the bird calls that play during the bridge. They're bright, cheerful, and contrast with the fast-paced melody.

It's best known to Australians as the music behind the Sydney Swans Rules of Football Club advertising campaign.

“West End Blues” by Louis Armstrong

Year: 1928

‘West End Blues' is a blues composition by Jo Oliver. It uses the 12-bar blues chord progression. Originally it was instrumental, but Clarence Williams later gave it words.

Other standout features of the Louis Armstrong version of ‘West End Blues' include the use of:

• Hand symbols
• Scat singing
• Trumpet cadenza

This opening cadenza is one of Armstrong's defining moments in his career. It's musically fluid and flexible in a way that anticipates the jazz of the 30s and 40s. Remarkably, the inspiration for the cadenza came from a trumpet exercise drill that Armstrong then improvised.

“Makin' Whoopee” by Eddie Cantor

Year:1929

Not all 1920s songs come from the early 20s. For example, late in the decade, ‘Makin' Whoopee' soared to popularity as sung by Eddie Cantor.

Much of its popularity hinges on the song's playfulness. It's a jazz-blues blend that playfully warns men of the perils and pitfalls of marriage. The recurring phrase “Makin' Whoopee” was a way to talk about intimate romantic relationships and avoid the music censors.

Today this popular song from the 1920s is remembered in the euphemistic phrase ‘Makin' whoopee,' which is still used euphemistically to talk about sex without being explicit.

In addition to Eddie Cantor, other famous artists who sang this song include:

• Bing Crosby
• Ella Fitzgerald
• Doris Day
• The King Cole Trio

“Dardanella” by Ben Selvin

Year: 1920

Ben Selvin first recorded ‘Dardanella' in 1919. Its popularity was such that he re-recorded it in 1920, and it became the first song to sell over three million copies.

This popular 1920s song was such a success that unauthorized recordings began appearing, despite copyright warnings in local magazines.

Other famous versions of this popular song from the 1920s include renditions by:

• Henry Burr
• Prince's Orchestra
• Harry Raderman

“Black and Tan Fantasy” by Duke Ellington

Year: 1927

No list of songs of the 1920s would be complete without a recording by Duke Ellington. ‘Black and Tan Fantasy' was one of Ellington's many jazz compositions.

While many of these were dance tunes, that's not the case with ‘Black and Tan Fantasy.' Instead, it's jungle jazz and showcases a particular African culture more expressive than dance music.

It was a staple at musical institutions like the Cotton Club, where it played an integral role in floor shows.

“Stardust” by Hoagy Carmichael

Year: 1927

You can't talk about 1920s songs without mentioning Hoagy Carmichael's ‘Stardust.'

Carmichael discovered jazz at university, and in ‘Stardust,' he created one of the jazz standards of the age. With Michael Parish's help, he gave the song lyrics.

Its popularity continued well past the 1920s. People were still singing this popular 1920s song in the 40s. Noteworthy performances include:

• Duke Ellington
• Art Tatum
• Fats Waller
• Ella Fitzgerald

“Yes, We Have No Bananas” by Ben Selvin

Year: 1923

Of all the 1920s songs on this list, ‘Yes We Have No Bananas' has the most fascinating history. Frank Silver and Irving Cohen wrote it after noticing the distinctive cadence of a Grecian fruit seller.

But this popular 1920s song quickly outgrew its humble origins. Because of its secular lyrics, it became the theme song for the outdoor relief protests in Belfast, where it uniquely united Catholics and Protestants.

It also became the anthem of British citizens faced with banana rationing during World War Two.

Despite its novelty origins, keen musical observers can hear several famous melodies in this song, including:

• The Hallelujah Chorus
• My Bonnie Lies Over the Ocean
• I Dreamed I Dwelt In Marble Halls
• Seeing Nellie Home
• An Old-Fashioned Garden

“Dinah” by Ethel Waters

Year: 1925

Harry Akst and Sam M. Lewis wrote ‘Dinah' in 1925. Ethel Waters was the first to sing it, using it as her introduction to the Plantation Club.

It gave Waters her start on Broadway and later became a musical number in ‘Kid Boots.'

In addition to Waters, other famous versions of the song came from:

• Cliff Edwards
• The Revelers
• Fanny Rose Shore

Shore's version was so ubiquitous that, in light of this 1920s song, she became known as ‘Dinah Shore.' The name stuck and remained her stage name for the rest of Shore's career.

“April Showers” by Al Jolson

Year:1921

From its opening chords, this popular song of the 1920s is lyric and romantic. Al Jolson sings a smooth, legato version with an orchestra to swoon to.

Louis Silvers and B.G. De Sylva wrote the song. Jolson premiered the song in the musical Bombo, and it soon became one of his signature songs.

Perhaps because of its overt sentimentality, ‘April Showers' was also a popular song in the 1920s to parody. Of these, the best-known features lyrics by Spike Jones and Doodles Weaver.

Memorably, the song was an integral part of a Morcombe and Wise skit that featured the comedians taking turns to douse each other with water.

The fun was had by more than comedians. In 1953, a judge sang ‘April Showers' after resolving a case between an orchestra and its leader.

“It Had to Be You” by Isham Jones

Year: 1924

Another song for your list of popular 1920s songs is ‘It Had to Be You.' Isham Jones wrote the song in 1924, and the original version is instrumental.

However, lyrics were written for it by Gus Kahn.

In a testament to the popularity of this song from the 1920s, it was featured in various film and television programs, including:

•  A Slight Case of Murder
• Casablanca
• Doctor Who

“St Louis Blues” by Louis Armstrong

Year:1929

You can't miss the bold, brassy opening of this popular 1920s song. Louis Armstrong's virtuosic trumpet playing immediately stands out, as does his singing when he takes over the vocal line.

W. C. Handy wrote ‘St Louis Blues' in 1914. It was one of the first blues songs there was. Today, it remains a popular jazz standard. In addition to Armstrong, notable performances include those by:

• Cab Calloway
• Count Basie
• Glenn Miller
• Boston Pops Orchestra

“Louise” by Maurice Chevalier

Year: 1929

Not all songs of the 1920s featured jazz or blues harmonies. ‘Louise' is an example of this. It's a lilting, melodic song.

The gently swung rhythm gives the music momentum and keeps it harmonically interesting.

Maurice Chevalier performed it first in the 1929 film Innocents of Paris and is immediately recognizable for his distinctive voice.

“Some of These Days” by Sophie Tucker

Year: 1926

Shelton Brooks wrote ‘Some of These Days' in 1910. But it was Sophie Tucker who turned it into a popular song of the 1920s.

Tucker heard the song in 1910 and realized it had the potential to be a musical hit. She recorded the song on a wax cylinder. When history proved her right about the popularity of ‘Some of These Days,' Ted Lewis and his orchestra accompanied Tucker on her famous 1926 recording.

The song was Tucker's signature piece, and she sang it often throughout her career.

“Always” by Vincent Lopez

Year: 1926

Irving Berlin wrote ‘Always' for his wife in 1926, which explains the swooping sentimentality of the orchestration.

The romance and musical accessibility of ‘Always' ensured it was one of the songs of the 1920s that everyone could and did sing.

However, most listeners will recognize it because of Noel Coward's wickedly clever appropriation of this popular favorite as a musical plot point in his play, ‘Blithe Spirit.'

Instead of being the loving serenade Berlin doubtless intends, Coward turns ‘Always' into the promise protagonist Charles Condomine's wife makes to him from beyond the grave. And when she successfully murders his second wife, she joins the ghostly persecution.

“Valencia” by Paul Whiteman

Year: 1926

Unlike other 1920s songs we've discussed, ‘Valencia' is a pasodoble or Spanish military march. It's this that gives the music its cut-time pace and musical momentum.

The lyrics were originally Spanish, but when the silent film Valencia made it one of the popular songs of the 1920s, it acquired English lyrics, too.

“I'll See You In My Dreams” by Isham Jones

Year:1924

This is another of the songs of the 1920s composed collaboratively by Isham Jones and Gus Khan. Like other 1920s songs, it has a noticeably long introduction before the words come in.

This intro style is common in 1920s music because dancing was still integral to how people met and socialized. You can hear this in the fast tempo of the music, which is perfect for the fast-paced dances of the time.

“Three O'clock in the Morning” by Paul Whiteman

Year: 1922

Speaking of dancing, ‘Three O'clock in the Morning' is a waltz by Julián Robledo. You can hear the lilting up-down of the dance cadence on the third beat of each bar.

Despite belonging to an older dance tradition than some of the songs of the 1920s on this list, when Paul Whiteman recorded it in 1922, it was tremendously popular. It was such a success it was one of the first recordings to sell over a million copies.

Don't forget to listen for the Westminster Quarters that opens and closes the song.

Best Songs From The 1920s, Final Thoughts

The popular songs of the 1920s vary from jazz to blues to lyrical, sentimental songs you can dance to. All hearken back to a fascinating time in musical history. Classical music was giving way to jazz, and musicians were becoming increasingly adventurous with their compositions.

While some of the songs of the 1920s have faded into obscurity, the ones that survive endure for a reason.