35 Popular Songs From The 1920s (Top Hits)

We all enjoy listening to older music that was popular during certain periods of time, such as the Roaring Twenties because it gives us a sense of what was going on historically and can bring back certain memories. Read further if you want to know about the 35 popular songs from the 1920s that were huge hits. 

1. Ol’ Man River – Paul Robeson 

Ol' Man River (Remastered)

First on our list is Ol’ Man River by Paul Robeson, which started as a song for Show Boat the musical in 1927, but his version was not made until 1928 and was more upbeat. Many components of Ol’ Man River are special, including the bass solo, which is not common in musicals. Another aspect is how social class and toil were being discussed, and the Mississippi River is discussed in metaphor form. 

2. Rhapsody In Blue – George Gershwin 

Next is Rhapsody In Blue by George Gershwin, which was released in 1924. There are piano and jazz elements to the song, and it first was performed at a concert in New York City that was called An Experiment In Modern Music. He is known for his piano playing, and this is one of his most well-known tunes. 

3. The Prisoner’s Song – Vernon Dalhart 

The Prisoner's Song

Vernon Dalhart is up next with his hillbilly tune The Prisoner’s Song, which was released in 1924. The backstory to the track is interesting because the cousin of Vernon, Guy Massey, might have heard this song from his brother while he was serving time in prison, and Massey sang it to Dalhart. Dalhart ended up copyrighting this track under the name of his cousin, and it became one of the top-selling tunes of the 1920s.

4. Dinah – Ethel Waters 

Ethel Waters – Dinah (The Plantation Revue)

Ethel Waters released Dinah in 1925, and it was part of the show Kid Boots. Several singers made versions of this song that were successful such as Fletcher Henderson and Fanny Rose Shore, but Waters was the one that initially had sung this track. The first time she sang the song was on Broadway at the Plantation Club.

5. Sweet Georgia Brown – Ben Bernie 

Sweet Georgia Brown

Next on our list is Ben Bernie with Sweet Georgia Brown, which was released in 1925, and this has become a jazz standard. A lot of musicians have covered this song over the years such as Nancy Sinatra, Jerry Lee Lewis, Charlie Parker, and Art Tatum. This was inspired by George Brown who had a daughter named Georgia. He named her after where she was born, and once Bernie heard this anecdote from Brown, he came up with the song. 

6. Charleston – Arthur Gibbs 

Up next is Arthur Gibbs with the song Charleston, which came out in 1923, and it’s one of the most iconic tracks of that decade. The musical on Broadway Running Wild is where this song first appeared, and it’s a mix of both ragtime and jazz. 

7. Stardust – Hoagy Carmichael 

Stardust (Remastered 2002)

Hoagy Charmichael released the jazz tune Stardust in 1927, and this song is a jazz standard that has now been recorded by other musicians more than 1,500 times. The track has been featured in The War Of The Worlds, The Flintstones, Casino, A Star Is Born, Another Man’s Poison, and Goodfellas.

8. Crazy Blues – Mamie Smith 

Next up on our list is Mamie Smith with Crazy Blues, which was released in 1920, and in a month, this record sold over 70,000 copies. What’s interesting about this song is that it was the first real blues track that was a hit. It’s still a hit song today with her version appearing in the popular television show Boardwalk Empire.  

9. Honey – Rudy Vallee 

In 1929, Rudy Vallee released Honey, and quickly, it became one of his biggest songs. This track is still incredibly popular since so many other artists have covered this song through the years. Haven Gillespie, Richard Whiting, and Seymour Simons were credited as writing the track, and it was used in Her Highness And The Bellboy, which was a movie from 1945. 

10. Black and Tan Fantasy – Duke Ellington 

Next is Duke Ellington with the song Black And Tan Fantasy, which was released in 1927, and this was one of several jazz tracks he released through the years. This song is different because it incorporated more of an African vibe, which is referred to as a jungle type of jazz. While a lot of his songs were popular in African culture, this was incredibly popular in institutions such as the Cotton Club. It’s still thought to be one of his top tracks to ever be released and is popular in black culture. 

11. Makin’ Whoopee – Eddie Cantor 

Our list has to include Makin’ Whoopee by Eddie Cantor, which was released in 1929, and while it was released later on in the 1920s, it easily became one of the biggest hits of that decade. It’s a blend of both blues and jazz that is meant to warn men about marriage and it got around censors by saying “whoopee.” This playful and fun song allowed people to talk about sex without mentioning the word by saying whoopee instead. Other musicians have covered this track such as Doris Day and Bing Crosby.

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12. Ain’t Misbehavin’ – Fats Waller 

Ain't Misbehavin' (Remastered)

In 1929, Fats Waller released the song Ain’t Misbehavin’, and it became one of the biggest tracks of the 1920s with several artists later covering it. Ella Fitzgerald, Louis Armstrong, and Nat King Cole all had their own versions of this song, but Waller has the original and best version. You can hear this track in movies and television shows such as Be Kind Rewind, The Russia House, The First Lady, and Pennyworth

13. Down Hearted Blues – Bessie Smith 

Down Hearted Blues (Digitally Remastered)

Next on our list is the 1922 hit by Bessie Smith called Down Hearted Blues. This song was her debut single, and within a few months after it was released, it had sold more than 750,000 copies. Powerful raw vocals are what set her version apart and become the most successful version of the track to be released. 

14. My Man – Fanny Brice 

Fanny Brice recorded an English version of the French song My Man in 1921, which became a hit for her and was featured in the 1928 movie My Man. The film is a comedy-drama and was just as popular as the track since she is in both. This song was such a success when it was translated into English that it led to her version entering the Grammy Hall Of Fame in 1999

15. You’d Be Surprised – Eddie Cantor 

You'd Be Surprised

In 1920, Eddie Cantor released You’d Be Surprised, which was a song that Irving Berlin wrote, and it became a huge success for Cantor. The track talks about a guy named Johnny, who is a great lover according to Mary, and no one else has thought of him to be such a good lover. He becomes a hit with the women thanks to her, and it’s just a funny and great song from that decade that people can relate to. 

16. Dardanella – Ben Selvin 

Next on our list is the 1920 hit song Dardanella by Ben Selvin, which he first recorded in 1919. However, it became such a hit he decided to record it again in 1920, which made it even more successful. It sold over three million records, and this was the first time a song had achieved that. There were copyright warnings for this track because it was such a popular tune that other records started popping up. 

17. Willie The Weeper – Louis Armstrong 

Louis Armstrong was a monumental figure during the 1920s, with his version of Willie The Weeper released in 1927. While the exact first recording of this song is a little mysterious, it first appeared between 1923 and 1926 and is credited to Freddie Keppard. It is about drug addiction, which makes it a relatable track even now. It has been recorded by several other artists through the years such as King Oliver and Ernest Rogers. 

18. Bye Bye Blackbird – Gene Austin 

Next on our list is Bye Bye Blackbird with the most famous version being recorded by Gene Austin in 1926. What makes his version unique is the introduction to the song, which most other artists didn’t put into their versions. 

Mort Dixon wrote the lyrics, and it was one of the most successful and influential songs of the 1920s. It was in movies such as Pete Kelly’s Blues. Another fact is that it was played during the Selma to Montgomery March by those that opposed the civil rights movement.

19. Pinetop’s Boogie Woogie – Pinetop Smith 

Pinetop's Boogie Woogie

We have to mention the song by Pinetop Smith called Pinetop’s Boogie Woogie. This track was released in 1928, and it is credited with creating boogie-woogie. For those of you who don’t know, it was the boogie-woogie genre that later led to rock and roll. 

20. Dark Was The Night (Cold Was The Ground) – Blind Willie Johnson 

Dark Was The Night (Cold Was The Ground)

Attention guitar fans, the 1927 song Dark Was The Night (Cold Was The Ground) by Blind Willie Johnson became a hit because it utilized the guitar over the banjo. This is an instrumental track that is a mix of gospel and blues, and he is heard only humming throughout the song instead of singing. The slide guitar used in this is exceptional for its time!

21. In The Jailhouse Now – Jimmie Rodgers 

In the Jailhouse Now by Jimmie Rodgers (1928)

Calling all banjo fans, one popular song of the 1920s is the version of In The Jailhouse Now by Jimmy Rodgers, which notably utilizes the banjo. He sings throughout the track while also playing the instrument, which is why it became so popular, and he also yodels in the song, which made his version unique. You can hear this track in the iconic movie O Brother, Where Art Thou? 

22. Sonny Boy – Al Jolson 

Al Jolson - Sonny Boy

In 1928, Al Jolson sang Sonny Boy for The Singing Fool, and it quickly became a hit, selling more than a million records. It topped the charts and stayed there for more than 12 weeks, making him a household name. This was featured in many television shows including Happy Days when it was sung at Arnold’s by Danny Thomas. It was also featured in Jeeves And Wooster where Hugh Laurie performs the song as he plays Bertie Wooster. 

23. Always – Vincent Lopez 

Next is Vincent Lopez with the song Always, which came out in 1926 and was written by Irving Berlin. He had written the track for his wife, and when you listen to this song, you can hear the love and sentimental aspects of it, making it one of the more popular love tracks of the decade. It was probably so popular since anyone could sing it.

It was notable in the play Blithe Spirit, but the song was turned into a dark tune in the play. In the play, the protagonist’s wife died, and this is used as the promise she makes, and he ends up killing his new wife. 

24. It Had To Be You – Isham Jones 

Attention fans of Doctor Who, you might know the song It Had To Be You by Isham Jones, which was released in 1924. The track was also featured in Casablanca and A Slight Case Of Murder, and it was one of the hit songs of the 1920s that originally started out as just an instrumental piece.

25. Valencia – Paul Whiteman 

Up next is Paul Whiteman and the song Valencia from 1926, which is a tune that is associated with the military march of Spain. There is a pace in this track that you can clearly hear, which makes sense when you know it’s a military march song. It’s an upbeat track that is powerful and has a lot of momentum that continues throughout the entire song. It was originally written in Spanish, but once the silent film was released, so were the lyrics in English. 

26. Louise – Maurice Chevalier 

We’re going to talk about the iconic voice of Maurice Chevalier and the 1929 song Louise, which is more of a slower rhythmic track than the common blues and jazz songs of that decade. It was different, and the momentum in the track keeps up to give it more of a smooth melody. The first time he performed this song was in Innocents Of Paris, which was a film that was released in 1929. 

27. I’ll See You In My Dreams – Isham Jones 

I'll See You in My Dreams

Next is the song I’ll See You In My Dreams, which was performed by Isham Jones and released in 1924. The track follows the pattern of 1920s tunes and doesn’t get into words until way into the tune. Longer introductions were common back then, and the fast tempo of the song works with the quick dances that were popular during the 1920s. 

28. Some Of These Days – Sophie Tucker 

Sophie Tucker "Some of These Days" on The Ed Sullivan Show

In 1926, Some Of These Days was released by Sophie Tucker even though the song had been written several years before in 1910. She heard it that year and decided to turn it into her own thing, thinking that it had potential. For several years, she would sing it during her concerts since it was known as her signature track. 

29. See See Rider Blues – Ma Rainey 

Attention blues fans, we’re going to talk about the 1924 song See See Rider Blues, which was performed by Ma Rainey. You may know this track because it was famously covered years later by the King of Rock and. Roll himself, Elvis Presley. This song is about a boyfriend that is a mooch and isn’t faithful, so it’s no wonder it became such a hit in the 1920s and beyond. Even though most people will remember Presley’s version since it was so popular, Ma Rainey’s version is still noteworthy. 

30. Match Box Blues – Blind Lemon Jefferson 

If you can relate to having financial difficulties then the next song Match Box Blues by Blind Lemon Jefferson is for you. This track was released in 1927 and is all about someone that is down on luck and has fallen on some hard times, so it’s relatable during times of financial insecurities. A notable cover of this song was done by The Beatles. 

31. King Porter Stomp – Fletcher Henderson 

Fletcher Henderson released the song King Porter Stomp in the 1920s with his band, which became one of the more well-known versions of the track. It was first released in 1923 by Jelly Roll Morton and is a jazz standard that has been covered by several artists through the years such as Harry James and Benny Goodman. 

32. In A Mist – Bix Beiderbecke 

Next is Bix Beiderbecke with In A Mist, which was from 1927, and it’s a piano composition that was a huge hit since it combined jazz and impressionism. Paul Whiteman put together a jazz concert in 1928, and he performed this song during that concert. This was a huge hit for him because it was just a piano recording of his own composition and it has such rich chords within it that it gives a very fast and zippy feel. 

33. Toot Toot Tootsie Goodbye – Al Jolson 

Toot Toot Tootsie Goodbye (Remastered)

We have to include the 1922 hit Toot Toot Tootsie Goodbye by Al Jolson, which is a very popular tune from the Roaring Twenties and is part of the flapper imagery. It first became a hit when it appeared in Bombo, a musical on Broadway. It quickly was covered by artists such as Eddie Cantor and Vincent Lopez, but Jolson’s version of the song remained the most popular. You can find this track in I’ll See You In My Dreams, The Jazz Singer, The Andy Griffith Show, and more. 

34. Yes, We Have No Bananas! – Billy Jones And Ben Selvin 

Yes, We Have No Bananas!

We have to include the 1923 hit song Yes, We Have No Bananas! by Ben Selvin and Billy Jones because it’s one of the coolest tracks on our list. The song quickly became a hit in Belfast where there were protests, and it united both the Protestants and Catholics. 

While the track was written by Irving Cohen and Frank Silver when they noted a cadence that a Greek fruit seller had, it turned into an anthem for several different types of people in various situations. For example, during WWII, there was banana rationing in Britain, so the British loved Yes, We Have No Bananas! as well.

35. I Want To Be Loved By You – Helen Kane 

I Wanna Be Loved by You

Last on our list is the 1928 song by Helen Kane called I Want To Be Loved By You, which was put on the RIAA list of Songs of the Century. This track was very popular and was written for Good Boy, which was a musical. Interestingly, the character Betty Boop was inspired by her, and Marilyn Monroe sang this song in Some Like It Hot.

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