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49 Popular Songs From the 1920s

December 22, 2023
Popular Songs From the 1920s

I’ve compiled a list of popular songs from the 1920s, a decade that revolutionized music with its jazz rhythms and lively melodies.

This article takes you back to the Roaring Twenties, exploring the timeless classics that still captivate audiences today.

Table of Contents

Top popular songs from the 1920s

  • “West End Blues” by Louis Armstrong
  • “Rhapsody In Blue” by Paul Whiteman ft. George Gershwin
  • “In The Jailhouse Now” by Jimmie Rodgers
  • “Ol’ Man River” by Al Jolson
  • “Crazy Blues” by Mamie Smith
  • “My Blue Heaven” by Paul Whiteman
  • “Whispering” by Paul Whiteman
  • “Black And Tan Fantasy” by Duke Ellington
  • “The Prisoner’s Song” by Vernon Dalhart
  • “My Man” by Fanny Brice

1. “West End Blues” by Louis Armstrong

West End Blues” is one of the best songs written and performed in the 1920s.

Joe “King” Oliver composed the jazz standard in 1928, which became popular through the celebrated jazz singer Louis Armstrong.

The “West End” refers to a renowned thriving resort in Orleans Parish, Louisiana, a popular resting point at the time. 

With “West End Blues,” Louis Armstrong wrote his name in the history books among the pioneers of jazz music. 

2. “Rhapsody In Blue” by Paul Whiteman ft. George Gershwin

The original version of “Rhapsody In Blue” came out in 1924, featuring George Gershwin and Paul Whiteman and his orchestra.

It is a beautiful blend of classical and jazz music that brings the nostalgic feelings of 1920s music.

The composition also brought out Gershwin’s distinctive style, putting him among the best composers and pianists of the century. 

3. “In The Jailhouse Now” by Jimmie Rodgers

The lighthearted tune about a man getting locked up in jail became one of the best songs of the 1920s.

The lyrics have evolved, but the original version is always credited to Jimmie Rodgers. 

Webb Pierce’s rendition became #1 in the country after release. 

In The Jailhouse Now” has traversed decades and has been covered by several artists, including Merle Haggard, Johnny Cash, Jim Jackson, and Pink Anderson, among the rest. 

4. “Ol’ Man River” by Al Jolson

“Ol Man River” became an anthem for the civil rights movement with its powerful message about hope and despair.

The original version appeared in Show Boat, a celebrated musical composed by Jerome Kern and Oscar Hammerstein II. 

But the civil rights activist Paul Robeson performed the most popular version.

The lyrics express defiance in the face of adversity, which resonated with many civil rights activists at the time.

Another famous crooner, Bing Crosby, also had success with the song.

Bing released his up-tempo version in 1928, featuring Paul Whiteman, and their rendition became a chart-topper. 

5. “Crazy Blues” by Mamie Smith

Mamie Smith made history when she recorded “Crazy Blues” in 1920.

It became the first song recorded by an African American artist to attract huge commercial success.

The song describes a woman’s pain at the hands of an abusive lover.

The lyrics resonated with many black Americans who faced abuses from rampant race-hate groups.

“Crazy Blues” became an instant success, selling about 75,000 copies within the first month of release. 

It also set the tone for a century of fiery fightback from the African Americans forced to battle the widespread discrimination at the time.

6. “My Blue Heaven” by Paul Whiteman

After Walter Donaldson composed the original version, George Austin added the lyrics to “My Blue Heaven” in the 1920s.

Shortly after its release, “My Blue Heaven” sold numerous copies and became one of the best-selling songs of the decade. 

The song is meant to be sung in a gentle, slow-tempo mood and has been covered by several artists, including the legendary Frank Sinatra. 

7. “Whispering” by Paul Whiteman

There couldn’t be a better way for Paul Whiteman to launch his career than the iconic jazz standard, which has since become one of the best songs of the 1920s.

“Whispering” is a sweet-sounding jazz song of the 1920s with an unmistakable, romantic melody.

The song stood out with its brilliant combination of several musical instruments.

Like most songs from the 1920s, “Whispering” lacked syncopation and had a simple harmony.

Such is its enduring popularity that there have been countless versions of “Whispering.”

8. “Black And Tan Fantasy” by Duke Ellington

“Black And Tan Fantasy” was written for a Harlem nightclub in the 1920s.

It was the mingling point for the African Americans and the whites.

“Black And Tan Fantasy” was another proof of Duke Ellington’s contribution to jazz music.

His inventive lyricism and matchless eloquence showed up throughout the narration, becoming one of his best-ever songs.

Despite releasing this song at the beginning of his career, it showed his versatility and unique musical style, setting him up for a career spanning over five decades.

9. “The Prisoner’s Song” by Vernon Dalhart 

Vernon Dalhart’s “The Prisoner’s Song” became one of the best-selling songs of the 1920s and one of the greatest prison songs in history.

The straightforward lyrics express a prisoner’s longing to go home.

The emotional narration endeared the track to music lovers, becoming one of the most popular songs from the 1920s. 

10. “My Man” by Fanny Brice

“My Man” was composed by Channing Pollock, Jacques Charles, and Maurice Yvain.

Fanny Brice’s 1921 version became a hit, describing a woman’s deep affection for her lover.

It is filled with heartbreaking that also made it popular amongst 1920s music lovers.

11. “Down Hearted Blues” by Bessie Smith

“Down Hearted Blues” is a sad song about broken love.

The lyrics described the heartache of a broken relationship and illustrated the pain of African Americans throughout the century.

It is regarded as one of the best songs that shaped rock music and a culturally significant composition that made history. 

The first line of the song sets the mood for the heartbreaking narration.

“Gee, but it’s hard to love someone when that someone doesn’t love you!” 

12. “Let’s Do It (Let’s Fall In Love)” by Bing Crosby

“Let’s Do It (Let’s Fall In Love)” is a popular song from the 1920s that is always credited to Bing Crosby.

But The Dorsey Brothers recorded the first-ever version, giving it an upbeat melody that has made it one of the most enduring songs of the century. 

The message of love and romance has made it popular throughout the century, covered by many artists and featured in multiple TV shows and films. 

13. “Blue Yodel #1 (T for Texas)” by Jimmie Rodgers

Jimmie Rodgers showed his unique musical style in “T For Texas,” a song about a journey through Texas.

It’s one of the earliest country songs with a catchy melody and memorable lyrics that traditional music lovers craved. 

Through “Blue Yodel #1,” Rodgers inspired other artists such as Ronnie Van Zant, George Harrison, and Johnny Cash. 

14. “Wildwood Flower” by Carter Family

“Wildwood Flower” tells the tale of lost love, with the man in the narration expressing his longing for a lost lover.

It was a hit for the famous Carter Family, featuring beautiful harmonies and instrumentation, making it one of the greatest songs of the 1920s. 

15. “Toot, Toot, Tootsie! (Goo’ Bye)” by Al Jolson

“Toot, Toot, Tootsie (Goo’ Bye)” tells the story of a man forced to watch as his lover leaves on a train.

The song captured the era of the Roaring Twenties.

And while Jolson’s version was the most recognizable, other successful renditions came from Ernest Hare & Billy Jones, Vincent Lopez, and the Benson Orchestra of Chicago. 

16. “Ain’t Misbehavin’” by Fats Waller

The lonely narrator in “Ain’t Misbehavin’” promises to be faithful to his lover no matter how tough the journey gets.

Andy Razaf wrote the original lyrics for the musical comedy play Connie’s Hot Chocolates. 

It has been covered by many artists, including Louis Armstrong, Ruth Etting, Gene Austin, and Bill Robinson, among the rest. 

17. “Bye Bye Blackbird” by Gene Austin

Bye Bye Blackbird” is a popular standard and one of the best songs from the 1920s.

It was composed by Mort Dixon and Ray Henderson and was first recorded in 1926 by Gene Austin.

There are multiple interpretations of the song’s lyrics, with some attributing them to a prostitute quitting the business to return home.

Other versions also say it is about a prostitute returning to the business.

No matter how you understand the lyrics, it is one of the most popular songs from the 1920s that resonates with anybody leaving someone or something behind. 

18. “Sweet Georgia Brown” by Ben Bernie

“Sweet Georgia Brown” goes back to the mid-1920s, written by Kenneth Casey, Maceo Pinkard, and Ben Bernie.

The song has been covered by many artists and adopted by sporting teams such as the Harlem Globetrotters exhibition basketball team. 

19. “Dark Was the Night” by Blind Willie Johnson

“Dark Was The Night” is a popular gospel song from the 1920s.

It was written and performed by Blind Willie Johnson and has been featured in several films.

It is a sad song about the loneliness of a homeless stranger, characterized by painful cries, moans, and groans.

20. “Dinah” by Ethel Waters

The original version of “Dinah” was written by Sam M. Lewis, Joe Young, and Harry Akst before becoming a hit for Ethel Waters. 

It’s a straightforward love song expressing a man’s affection for this beautiful girl named Dinah.

The beloved tune stood out with its catchy lyrics and has since become one of the best songs of the 1920s. 

21. “Some of These Days” by Sophie Tucker

“Some of These Days” was originally written by Shelton Brooks in 1910 before becoming a hit for Sophie Tucker in the mid-1920s.

It is a women empowerment anthem encouraging the ladies to find love and happiness no matter how long it takes.

The lyrics spread a message of hope which resonated with just about anyone starting from the bottom of the ladder with aspirations to rise to the top. 

22. “Always” by Vincent Lopez

“Always” is another song from the 1920s that has become extremely popular amongst contemporary listeners.

It stood out with the poignantly romantic lyrics and the uplifting melody and has been covered by several artists, including Nick Lucas, George Olsen, and Henry Burr. 

23. “I’ll See You In My Dreams” by Isham Jones

The narrator of “I’ll See You In My Dreams” uses wistful lyrics to reminisce about his broken love.

The song is rated highly among the most romantic ballads from the 1920s and holds a special place in many people’s hearts. 

Other popular renditions continue the nostalgic and sentimental themes and include Pat Boone’s, Eddie Cochran’s, and The Pearls,’ to mention a few. 

24. “Three O’clock in the Morning” by Paul Whiteman

Paul Whiteman’s romantic ballad looks at the narrator’s longing for the intimacy of 3 am. 

The lyrics are delivered with a gentle melody that validates the song’s intimate atmosphere. 

The song can relate to anyone who’s had those intimate moments at 3 o’clock. 

25. “Tea For Two” by Marion Harris

“Tea For Two” first appeared in the 1925 No, No Nanette musical and has become one of the most popular songs from the decade.

The earliest versions are attributed to Vincent Youmans and Irving Caesar.

It became a jazz standard in the later years, covered by bands and artists such as Benny Goodman, Anita O’Day, Frank Sinatra, and Doris Day.

26. “Pine Top’s Boogie Woogie” by Pine Top Smith

“Pine Top’s Boogie Woogie” is one of the earliest piano instrumentals that laid the foundation for the genre.

It is sometimes called “the first rock and roll song” and greatly influenced the 1920s music artists. 

27. “Swanee” by Al Jolson

“Swanee” is another song from the 1920s that Al Jolson popularized.

It is an upbeat tune about an intense yearning for home, a place called Swanee.

The catchy melody has made it a timeless classic, popular among jazz listeners and artists. 

28. “Makin’ Whoopee” by Eddie Cantor

One of the best songs from the 1920s describes intimate sexual relations. 

“Makin’ Whoopee” is a jazz song made popular by Eddie Cantor in the Whoopee! musical of 1928. 

It follows a couple’s journey from the wedding to the honeymoon, reaching the climax in the bedroom. 

It ends with babies, responsibilities, affairs, divorce, and the court’s judgment. 

Ultimately, the song served as a warning to men about marriage.

29. “Sonny Boy” by Al Jolson

Lew Brown, Buddy De Sylva, and Ray Henderson wrote “Sonny Boy” in 1928 to describe father-son love, and it became an instant hit. 

The emotional lyrics have made it a beloved song throughout the century, with many listeners marveling at Al Jolson’s magical vocals. 

Jolson’s version was a #1 hit for 12 weeks, selling about a million units. 

30. “See See Rider Blues” by Ma Rainey

“See See Rider Blues” is a timeless classic that confirmed Ma Rainey as one of the best vocalists from the 1920s.

The first version was recorded in 1924 and told the tale of an unfaithful lover, sometimes called an “easy rider.”

Elvis Presley enjoyed major success with his 1962 rendition of “See See Rider.”

31. “I Wanna Be Loved by You” by Helen Kane with Leonard Joy’s Orchestra

Most of us are going to be familiar with this one from the fictional character Betty Boop. 

The inspiration behind the naughty character was Helen Kane.

This track was written for another musical entitled Good Boy (they were wildly popular in the 20s). 

It soon became her signature song.

It was recorded by her in 1928 and she became known for her cute scat-like “boop-boop-a-doop”.

Some even referred to Helen as the “boop-boop-a-doop girl”!

But that helped her little when she insisted the company had stolen from her intellectually with their cartoon character.

The iconic Marilyn Monroe reprised the track in the musical Some Like It Hot.

32. “It Had to Be You” by Marrion Harris

Marrion Harris was one of the leading singers of the 1920s many of her tracks were cherished by the public.

One that is fondly remembered is this one composed by Isham Jones.

It was recorded instrumentally by the Isham Jones Orchestra in 1924.

Then lyrics were scribed by Gus Khan and Marrion Harris recorded it in Brunswick Studios very soon after.

It was featured in several films that followed including Melody in May (1936) and Casablanca (1942).

33. “I Can’t Give You Anything But Love” by Cliff Edwards 

Yet another track that went on to become immortalized as a jazz standard…

This one was originally part of the Blackbirds of 1928 Broadway musical revue with music by Jimmy McHugh and lyrics by Dorothy Fields.

“I Can’t Give You Nothing” was one of the songwriting duo’s first hits.

The entire revue went down a storm.

The lyrics were humorously posed despite the downcast themes.

Being so instantly popular, many performed it in the 1920s.

We have chosen the version by Cliff Edwards.

With so many renditions of the much-loved hit, it went on to inspire an entire comedy film built around it with the same title in 1940.

34. “If You Knew Susie Like I Know Susie” by Eddie Cantor

Another humorous track with a similar vibe was “If You Knew Susie Like I Know Susie”.

Written in 1925 by Buddy DeSylva and Joseph Meyer, this one was first offered to Al Jolson, one of the most famed performers of the era.

But, it was destined to be one of Eddie Cantor‘s biggest hits instead.

Jolson did indeed record it but wasn’t very interested in it.

He passed it on to his protegé who saw far more success.

So much so that Jolson later candidly expressed regret for not releasing it publicly!

35. “St. Louis Blues” by Bessie Smith

This one was marginally composed in 1914 by W. C Handy and became a staple in the repertoires of the jazz greats such as Benny Goodman, Cab Calloway, and Bing Crosby.

Although the title suggests it is a blues track, and it does contain some key elements in the composition that went on to become a staple for the 12-bar blues it has a ragtime feel. 

Many blues musicians reject it for that reason.

The first person to perform it publicly was singer and actress Ethel Waters in 1917.

But it was made famous when Bessie Smith debuted it with Louis Armstrong on trumpet in 1925. 

She later went on to star in the motion picture with the same name in 1929 bringing it to a wider audience.

36. “Someone to Watch Over Me” by Gertrude Lawrence 

This George and Ira Gershwin number was written for the 1926 musical Oh, Kay!

It was first sung on Broadway by English actress Gertrude Lawrence and that is the version we have decided to highlight in today’s list of popular songs from the 1920s.

Close to 2,000 versions of this song now exist, which goes to show its immortality as a jazz standard.

Some of the diverse artists to have given it a go include Frank Sinatra, Ella Fitzgerald, Barbara Streisand, Ray Charles, Elton John, and Amy Winehouse.

37. “Rhapsody in Blue” by George Gershwin

Paul Whiteman’s orchestra is back in our sights for this 1920s hit once again the music arranged by Ferde Grofé.

Gershwin composed this one with a beautiful solo piano backed orchestrally.

It became one of his defining instrumentals and helped shape early jazz.

The 1924 track had some stunning motifs and dynamics and established Gershwin as one of the greatest composers of his generation.

For its time it was pretty experimental, it debuted at Aeolian Hall in Manhattan as part of a premier entitled An Experiment in Modern Music.

It received a standing ovation from the audience, enamored. 

38. “Yes Sir! That’s My Baby” by Gene Austin & Billy Carpenter

From the minds of Gus Khan and Walter Donaldson sprung this simple tune.

The Charleston song was supposedly inspired by a clockwork walking pig toy that had a rhythm to it that Singer Eddie Cantor’s daughter was playing with, in the background of the same room.

Margaret Young released the first version in 1925 and in that same year, Ace Brigode, Gene Austin, Blossom Seeley, and Ben Bernie all gave us a rendition.

Cantor himself was late to jump on the bandwagon, recording it in 1930.

39. “April Showers” by Al Jolson

Jolson was one of the greats, a prevalent singer in the roaring twenties.

In 1921 Louis Silvers and Buddy De Sylva penned this sweet track for Jolson. 

It was used for the 1922 Broadway musical Bombo which, to be honest, fell short of a plotline and didn’t make it to modern audiences because of its flagrant racism.

Blackface and stereotyping aside, this song had some thoughtful lyrics that reminded you not to feel down because better days are ahead.

Which was exactly what people wanted to hear following WW1 and so the song lived on.

“Though April showers may come your way

They bring the flowers that bloom in May”.

40. “Me and My Shadow” by Whispering Jack Smith

Yet another cracking jazz standard with introspective lyrics that capture the sense of loneliness.

With only the company of your shadow, Jack’s subtle vocal delivery style that earned him his “whisperin’” nickname adds to the loneliness.

We can’t stress the popularity of this one, it has endeavored for almost a century and will probably continue to be sung forevermore.

The list of famous covers is endless.

The 1927 song by Whispering Jack Smith is credited to Al Jolson, Billy Rose, and Dave Dreyer but officially only Billy Rose wrote it. 

False credits were very common in the 1920s; they helped push the popularity of a piece.

Jolson was such a household name that if he had anything to do with it people would listen!

41. “Singin’ in the Rain” by Cliff Edwards

Unless you live under a rock, you’ll likely recognize this one from the 1952 Movie with the same title starring Gene Kelly.

That scene of him dancing in the street as the heavens pour is iconic and melded into our memories.

Well, the song was originally composed in 1929 by Nacio Herb Brown with lyrics by Arthur Freed that we all know and love.

There are endless contemporary versions but Cliff Edwards, also known as “Ukelele Ike”, was one of the first.

It is faster, with a ragtime rhythm.

You may recognize his voice as Jiminy Cricket from Walt Disney’s Pinocchio!

42. “Somebody Stole My Gal” by Ted Weems and His Orchestra

Leo Wood composed this instrumental in 1918 and in 1924 an arrangement by Ted Weems and His Orchestra brought it to wider audiences. 

The 20s rendition sold over a million copies and it has been used in the soundtracks of many Hollywood movies.

There is something very “quintessentially twenties” about it.

The banjo and ukes delightfully propel the track along and the brass has that classic wah-wah-wah tonality and lots of dynamic mute use.

43. “Dardanella” by Ben Selvin

This one was written, recorded, and released in 1919 but the height of its popularity peaked in 1920.

This was largely due to many unauthorized copies making it to the masses.

Something that was rife during the 1920s 

Composers Felix Bernard and Johnny S. Black even went to the lengths of publishing an ad to warn people not to “imitate, copy or steal any part of ‘Dardanella’.” 

The advert was addressed to “thieves and pirates”!

The popular foxtrot became the second-biggest-selling record of the year.

Lyrics were added later and Bing Crosby went on to duet a version with Louis Armstrong in the 1960s.

44. “Blue Skies” by Irving Berlin

Post-war bluebirds became a real symbol of happiness and still are today.

“Blue Skies” is just one of many examples of songs that came out of the 1920s with bluebirds in the lyrics

“Blue skies smiling at me.

Nothing but blue skies do I see.

Blue bird singing a song.

Nothing but blue birds all day long.

Never saw the sun shining so bright.”

This one was again written by Irving Berlin and many people sang it but it is synonymous with the Ben Selvin Orchestra who recorded a version with Charles Kaley on vocals.

It is short and sweet with an abrupt ending.

It was a last-minute addition to the short-lived 1926 Rodgers and Hart musical Betsy.

45. “Ain’t We Got Fun?” by Van & Schenck

In 1921 Gus Khan wrote the lyrics to this popular song aided by Raymond B. Egan over the upbeat foxtrot composed by Richard A. Whiting.

The music is very contrasting to the lyrics which make commentary on disparity and separation of classes.

They were pretty poignant.

“The rich get richer and the poor get children.”

Khan used very colloquial phrases and the grammatical structure was abandoned.

Some of the words of wisdom in this one went on to be quoted elsewhere a bit like the modern meme. 

Some of the lines are used in The Great Gatsby.

46. “Ain’t She Sweet?” by Gene Austin

You might recognize this sugary love song thanks to the 1961 cover by the infamous Liverpool four-piece.

The Beatles made it their own as many others tried to do before them.

The 1927 track was composed by Milton Ager for his daughter.

The lyrics were courtesy of Jack Yellen and Gene Austin provided the vocals

There are versions by Ben Bernie with Scrappy Lambert & Billy Hillpot that were all released in the same year.

47. “The Birth of the Blues” by Harry Richman

We already mentioned “Bye Bye Blackbird” composed by Ray Henderson but that same year (1926) he brought us this classic.

The lyrics were written by Buddy DeSylva and Lew Brown and told a narrated tale of how the blues came to be.

The supposed ingredients behind “The Birth of the Blues” as detailed in the song were the breeze through the trees and the wails of a downhearted prisoner.

It was recorded by Paul Whiteman’s orchestra with Harry Richman taking the vocals.

It has some great imagery and went on to become a staple famously covered by Crosby, Sinatra, and other crooners to come.

48. “Honeysuckle Rose” by Thomas “Fats” Waller

This popular song from the ‘20s made an appearance right before the turn of the decade as part of the 1929 Off-Broadway revue Load of Coal.

It is a jazz staple that went on to have many successful renditions throughout the ‘30s and ‘40s.

The lyrics were surprisingly raunchy with a lot of what would now be considered double-entendre passed off as beautiful sentiment.

Subsequent versions even had an additional verse that could be considered quite graphic if you read well enough between the lines!

49. “Yes! We Have No Bananas” by Billy Jones (1923)

We are finishing with an infamous American novelty song by Frank Silver and Irving Cohn.

The backstory for the title, this one as described by Silver, was inspired by a Greek fruit stall merchant who began every sentence with “yes” as he spoke to customers and passers-by.

Now at the time, Panama disease wiped out banana crops and so the jaunty and comical song was born.

It became a hit for Billy Jones, though many others recorded it too!

As far as sheet-music sales go it is still among one of the best-selling in American history!

Popular Songs from the 1920s – Final Thoughts

The 1920s should never be overlooked when looking for the best songs that shaped popular culture.

This was the era of jazz and blues music with timeless hits that have traversed generations. 

From the romantic ballads of Paul Whiteman to the passionate jazz of Duke Ellington, this era was special for many reasons. 

While some songs from the decade might have faded forever, our popular songs from the 1920s have endured the changes.

Listen to them to see how they helped shape the century. 

You may also like: Best Songs From the 40s

Will Fenton

Will, the founder of MIDDER, is a multifaceted individual with a deep passion for music and personal finance. As a self-proclaimed music and personal finance geek, he has a keen eye for futuristic technologies, especially those that empower creators and the public.

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