100 Greatest Songs from 1920s

The Roaring Twenties was a decade of cultural, artistic, and social revolution, and the music of the era was no exception. From the rise of jazz and blues to the emergence of new technologies that allowed for mass production and distribution of music, the 1920s saw a vibrant and diverse musical landscape. In this article, we explore the top 100 greatest songs from 1920, a year that marked the beginning of this transformative decade. These songs capture the spirit of the times, with their infectious melodies, playful lyrics, and raw emotion. From the mournful ballads of Al Jolson and Paul Whiteman to the energetic jazz of Louis Armstrong and Duke Ellington, the songs of 1920s are a testament to the power of music to both reflect and shape the culture of a time. Join us on a journey through the sounds of the past as we explore the top 100 greatest songs from 1920, and discover the music that shaped a generation.

1. Swanee – Al Jolson

“Swanee” is a popular song written by George Gershwin and Irving Caesar and made famous by Al Jolson in 1919. It is a lively and upbeat tune that has become a standard in American popular music. The song features Jolson’s signature style of singing, which includes his distinctive vibrato and use of yodeling. The lyrics tell the story of a man who is longing to return to his home in the South, specifically the town of Swanee. The song has been covered by many artists over the years and has appeared in numerous films, including Jolson Sings Again (1949). “Swanee” is a timeless classic that continues to captivate audiences with its catchy melody and memorable lyrics.

2. West End Blues – Louis Armstrong

“West End Blues” is a jazz standard written by Joe King Oliver and made famous by Louis Armstrong in 1928. The song is notable for Armstrong’s powerful trumpet solos and his use of the “stop-time” technique, where the band stops playing and the soloist plays alone. The song features complex harmonies and rhythms, and the lyrics describe the vibrant atmosphere of New Orleans’ West End neighborhood. “West End Blues” is considered one of Armstrong’s greatest recordings and has been hailed as a landmark in the history of jazz. The song has been covered by many jazz musicians over the years and remains a staple in the jazz repertoire. “West End Blues” is a testament to the enduring legacy of Louis Armstrong and his contributions to the development of jazz music.

3. Rhapsody In Blue – Paul Whiteman featuring George Gershwin

“Rhapsody in Blue” is a musical composition by George Gershwin, premiered in 1924 and featuring Paul Whiteman and his orchestra. The piece is a fusion of classical and jazz music, showcasing Gershwin’s unique style and his ability to blur the boundaries between genres. The composition features a distinctive opening clarinet solo, followed by a soaring melody played by the orchestra. “Rhapsody in Blue” is considered one of Gershwin’s most famous works and has been used in numerous films, commercials, and TV shows. The piece is a testament to Gershwin’s innovative spirit and his lasting impact on American music.

4. Ain’t Misbehavin’ – Fats Waller / Louis Armstrong

“Ain’t Misbehavin'” is a jazz standard written by Fats Waller and Harry Brooks in 1929, with lyrics by Andy Razaf. The song has been covered by many artists over the years, including Louis Armstrong, and is known for its catchy melody and playful lyrics. The song expresses a carefree attitude towards life and love, and has become a classic in American popular music. The song’s upbeat tempo and joyful melody have made it a favorite for dancers and jazz enthusiasts alike.

5. T For Texas (Blue Yodel #1) – Jimmie Rodgers

“T For Texas (Blue Yodel #1)” is a country blues song written and recorded by Jimmie Rodgers in 1927. The song features Rodgers’ distinctive style of singing, which includes his use of yodeling and falsetto. The lyrics describe a man’s journey through Texas, and the song has become a classic in the country music genre. The song’s catchy melody and sing-along chorus have made it a favorite among fans of early country music.

6. In The Jailhouse Now – Jimmie Rodgers

“In The Jailhouse Now” is a blues song written and recorded by Jimmie Rodgers in 1928. The song tells the story of a man who repeatedly finds himself in jail for various misdeeds. The song’s humorous lyrics and catchy melody have made it a popular tune among fans of early blues music. The song has been covered by many artists over the years, including Johnny Cash and Webb Pierce, and remains a classic in the country blues genre.

7. The Prisoner’s Song – Vernon Dalhart

“The Prisoner’s Song” is a popular ballad written by Guy Massey and Vernon Dalhart and recorded by Dalhart in 1924. The song tells the story of a prisoner who longs to be reunited with his loved one. The song’s poignant lyrics and emotional melody struck a chord with audiences, and it became one of the best-selling songs of the 1920s. “The Prisoner’s Song” has been covered by many artists over the years, and its enduring popularity is a testament to the power of storytelling in music.

8. The St. Louis Blues – Bessie Smith / Marion Harris

“The St. Louis Blues” is a blues song written by W.C. Handy and recorded by Bessie Smith in 1925. The song tells the story of a woman who has been mistreated by her lover and is now seeking revenge. The song’s haunting melody and powerful lyrics have made it a classic in the blues genre. The song has been covered by many artists over the years, including Louis Armstrong and Cab Calloway, and remains a staple in the American popular music canon.

9. Ol’ Man River – Paul Robeson / Al Jolson

“Ol’ Man River” is a show tune from the musical Show Boat, with music by Jerome Kern and lyrics by Oscar Hammerstein II. The song has been recorded by many artists over the years, including Paul Robeson and Al Jolson, and is known for its powerful lyrics and moving melody. The song expresses the struggles of the African American people and their history of oppression in America. “Ol’ Man River” remains a powerful anthem for civil rights and social justice.

10. Makin’ Whoopee – Eddie Cantor/ Paul Whiteman (Bing Crosby)

“Makin’ Whoopee” is a popular jazz song from the 1920s, written by Walter Donaldson and Gus Kahn. The song describes the ups and downs of married life, particularly the unglamorous aspects of romance. Eddie Cantor and Paul Whiteman’s version of the song features a witty, playful vocal performance from Cantor and a lively, swinging arrangement from Whiteman’s orchestra. Bing Crosby would later record a popular version of the song, which became one of his signature tunes. “Makin’ Whoopee” became a popular standard, covered by many jazz and pop artists over the years.

11. Crazy Blues – Mamie Smith

“Crazy Blues” is a blues song recorded by Mamie Smith in 1920. It was the first blues recording by an African American artist to achieve wide commercial success, and it helped to establish the blues as a popular genre. The song’s lyrics describe the pain and heartbreak of a failed relationship, with Smith’s powerful vocals conveying a sense of emotional intensity. “Crazy Blues” was a landmark recording that helped to pave the way for the blues and other African American musical styles to gain wider acceptance.

12. My Blue Heaven – Gene Austin / Paul Whiteman

“My Blue Heaven” is a popular song from 1927, with music by Walter Donaldson and lyrics by George Whiting. The song was first recorded by Gene Austin and became a massive hit, selling millions of copies and becoming one of the best-selling songs of the 1920s. The song’s gentle melody and sentimental lyrics evoke a sense of nostalgia for a simpler, more innocent time. “My Blue Heaven” has been covered by many artists over the years, including Paul Whiteman, Fats Domino, and Frank Sinatra.

13. Sonny Boy – Al Jolson

“Sonny Boy” is a song from 1928, with music by Ray Henderson and lyrics by Bud DeSylva, Lew Brown, and Al Jolson. Jolson’s recording of the song was a huge hit, and it became one of his signature tunes. The song’s lyrics describe the joy of fatherhood and the love that a father feels for his son. Jolson’s powerful vocals and emotional delivery helped to make “Sonny Boy” a beloved classic that has endured for nearly a century.

14. Dardanella – Ben Selvin

“Dardanella” is a popular song from 1919, with music by Felix Bernard and lyrics by Johnny S. Black. The song was first recorded by Ben Selvin and His Orchestra and became a massive hit, selling millions of copies and becoming one of the best-selling songs of the decade. The song’s catchy melody and upbeat tempo helped to make it a favorite of jazz and dance bands of the era. “Dardanella” has been covered by many artists over the years, including Louis Armstrong, Fats Waller, and Benny Goodman.

15. It Had To Be You – Isham Jones / Marion Harris

“It Had to Be You” is a popular song from 1924, with music by Isham Jones and lyrics by Gus Kahn. The song was first recorded by Marion Harris and became a hit, later becoming a popular standard that has been covered by many artists over the years. The song’s romantic lyrics and gentle melody evoke a sense of longing and nostalgia for a lost love. “It Had to Be You” has been covered by many jazz and pop artists over the years, including Frank Sinatra, Tony Bennett, and Harry Connick Jr.

16. Pine Top’s Boogie Woogie – Pine Top Smith

“Pine Top’s Boogie Woogie” by Pine Top Smith is a classic boogie woogie piano instrumental that is considered one of the earliest and most influential recordings of the genre. Released in 1928, the song features Pine Top’s virtuosic piano playing, characterized by a driving rhythm, playful melodies, and intricate improvisations. The song’s popularity helped establish boogie woogie as a mainstream style and influenced numerous musicians, including Albert Ammons, Pete Johnson, and Meade Lux Lewis.

17. Whispering – Paul Whiteman

“Whispering” by Paul Whiteman is a jazz standard from 1920 that features a sweet and romantic melody played by a large orchestra. The song’s popularity is due in part to the beautiful harmonies created by the blending of different instruments, including saxophones, trumpets, and violins. The song has been covered by numerous artists over the years, including Frank Sinatra and Billie Holiday.

18. My Mammy – Al Jolson / Paul Whiteman

“My Mammy” is a classic song from the musical “The Jazz Singer” that was performed by Al Jolson in the 1927 film adaptation. The song’s lyrics express the singer’s love and devotion to his mother, and it is notable for Jolson’s emotive and theatrical singing style. The song was also famously performed by Paul Whiteman, whose 1928 recording features a lively jazz band arrangement.

19. Down Hearted Blues – Bessie Smith

“Down Hearted Blues” by Bessie Smith is a classic blues song from 1923 that features Smith’s powerful and soulful vocals backed by a small jazz ensemble. The song’s lyrics express the pain and heartache of a broken relationship and reflect the struggles faced by many African Americans during the early 20th century. The song’s popularity helped establish Smith as one of the most important and influential blues singers of all time.

20. Charleston – Arthur Gibbs /Paul Whiteman

“Charleston” by Arthur Gibbs and Paul Whiteman is a lively jazz instrumental that was popular during the 1920s. The song features a catchy melody played by a large orchestra, with solos from various instruments including clarinet, trumpet, and trombone. The song’s popularity helped to popularize the Charleston dance, which became a cultural phenomenon during the Roaring Twenties.

21. Black And Tan Fantasy – Duke Ellington

“Black and Tan Fantasy” is a jazz composition by Duke Ellington and Bubber Miley, released in 1927. The song’s title refers to the Black and Tan Club, a popular nightclub in Harlem during the 1920s where African American and white patrons would mingle. The song’s haunting melody and unusual instrumentation, including the use of a muted trumpet, create a dreamlike atmosphere that evokes the atmosphere of the club. The song is considered a masterpiece of early jazz and has been covered by many musicians over the years.

22. See See Rider Blues – Ma Rainey

“See See Rider Blues” by Ma Rainey is a classic blues tune that showcases Rainey’s powerful vocals and soulful delivery. Originally recorded in 1924, the song tells the story of a woman who leaves her lover and heads to Memphis on a train called the “See See Rider.” The track features a simple, yet infectious melody that is easy to sing along to, and Rainey’s emotive vocals bring the lyrics to life. The song has been covered by numerous artists over the years, including Elvis Presley, who scored a hit with his version in 1962.

23. Statesboro Blues – Blind Willie McTell

“Statesboro Blues” by Blind Willie McTell is a haunting and melancholy blues tune that features McTell’s distinctive slide guitar playing and mournful vocals. Originally recorded in 1928, the song tells the story of a man who is down on his luck and contemplating suicide. The lyrics are filled with vivid imagery, such as “I’m going to get me a mojo hand / I’m going to have all you women / Right here at my command.” The track has been covered by many artists over the years, including the Allman Brothers Band, who recorded a popular version in 1971. McTell’s unique guitar style and emotional delivery have made “Statesboro Blues” a timeless classic in the blues genre.

24. Matchbox Blues – Blind Lemon Jefferson

“Matchbox Blues” by Blind Lemon Jefferson is a classic blues tune that features Jefferson’s intricate fingerpicking guitar style and soulful vocals. Originally recorded in 1927, the song tells the story of a man who is down on his luck and has nothing left but a matchbox to his name. The lyrics are filled with vivid imagery and metaphors, such as “I’m sitting here wondering, will a matchbox hold my clothes?” The track has been covered by many artists over the years, including the Beatles, who recorded a version in 1964.

25. Bye Bye, Blackbird – Gene Austin / Nick Lucas

“Bye Bye, Blackbird” is a popular jazz standard that has been covered by many artists over the years, including Gene Austin and Nick Lucas. Originally written in 1926, the song tells the story of a man who is saying goodbye to a lover and heading out on the road. The track features a catchy melody and upbeat tempo, and the lyrics have a bittersweet quality that captures the feeling of leaving someone behind. The song has been recorded in many different styles, from jazz to pop to rock and roll.

26. King Porter Stomp – Fletcher Henderson / Jelly Roll Morton

“King Porter Stomp” is a classic jazz tune that was first recorded by Fletcher Henderson in 1928. The track features a lively melody and infectious rhythm that showcase the talents of Henderson’s big band, which included some of the top musicians of the era. The song was later covered by jazz legend Jelly Roll Morton, who claimed to have written it himself. “King Porter Stomp” has become a jazz standard and has been recorded by many artists over the years, including Benny Goodman and Glenn Miller.

27. California, Here I Come! – Al Jolson

“California, Here I Come!” is a classic song from the 1920s that was popularized by Al Jolson. The track features a catchy melody and upbeat tempo that capture the spirit of the Roaring Twenties. The lyrics tell the story of a man who is heading to California in search of a better life. The song has become an anthem for the Golden State and has been covered by many artists over the years, including Ray Charles and the Beach Boys.

28. In A Mist – Bix Beiderbecke

“In A Mist” is a jazz composition by Bix Beiderbecke that was first recorded in 1927. The track features Beiderbecke’s distinctive cornet playing and a haunting melody that showcases his talent for improvisation. The song has become a jazz classic and has been recorded by many artists over the years, including Duke Ellington and Benny Goodman. “In A Mist” is considered to be one of Beiderbecke’s signature tunes and is a testament to his enduring influence on the jazz genre.

29. Waiting For A Train – Jimmie Rodgers

“Waiting For A Train” is a country blues song recorded by Jimmie Rodgers in 1928. The track features Rodgers’ distinctive yodeling style and tells the story of a man who is waiting for a train to take him away from his troubles. The song’s simple yet powerful lyrics and memorable melody have made it a classic of the country blues genre. Over the years, “Waiting For A Train” has been covered by many artists, including Johnny Cash and Merle Haggard.

30. Louise – Maurice Chevalier

“Louise” is a French song made famous by Maurice Chevalier in 1929. The track features Chevalier’s smooth vocals and a lively melody that captures the essence of Parisian nightlife. The lyrics tell the story of a man who is in love with a woman named Louise and longs to be with her. “Louise” has become a beloved classic of the chanson genre and has been covered by many artists over the years.

31. Star Dust – Hoagy Carmichael

“Star Dust” is a jazz standard composed by Hoagy Carmichael in 1927. The track features a haunting melody and poetic lyrics that capture the feeling of nostalgia and lost love. Over the years, “Star Dust” has been covered by many artists, including Louis Armstrong and Nat King Cole. The song has become a jazz classic and is considered one of the greatest songs of the 20th century.

32. Yes! We Have No Bananas – Billy Jones / Ben Selvin

“Yes! We Have No Bananas” is a novelty song recorded by Billy Jones and Ben Selvin in 1923. The track features a catchy melody and playful lyrics that tell the story of a grocery store that has run out of bananas. The song was a huge hit and has become a classic of the vaudeville era. Over the years, “Yes! We Have No Bananas” has been covered by many artists and has been featured in numerous films and television shows.

33. Yes Sir That’s My Baby – Gene Austin / Blossom Seeley / Ben Bernie

“Yes Sir That’s My Baby” is a jazz standard that was popularized by Gene Austin in 1925. The track features a catchy melody and upbeat tempo that capture the spirit of the Roaring Twenties. The lyrics tell the story of a man who is in love with a woman and is proud to call her his own. Over the years, “Yes Sir That’s My Baby” has been covered by many artists, including Frank Sinatra and Dean Martin.

34. Toot Toot Tootsie (Goo’Bye) – Al Jolson

“Toot Toot Tootsie (Goo’Bye)” is a classic song from the 1920s that was popularized by Al Jolson. The track features Jolson’s signature style of singing and a catchy melody that captures the spirit of the Roaring Twenties. The lyrics tell the story of a man who is saying goodbye to a lover and heading out on the road. Over the years, “Toot Toot Tootsie (Goo’Bye)” has been covered by many artists, including Nat King Cole and Louis Armstrong.

35. Sweet Georgia Brown – Ben Bernie / Isham Jones / Ethel Waters

“Sweet Georgia Brown” was written in 1925 by Ben Bernie, Maceo Pinkard, and Kenneth Casey. It became a popular jazz standard and has been recorded by many artists. The song’s lively melody and catchy lyrics have made it a favorite among jazz musicians and fans alike. The song’s lyrics celebrate the state of Georgia and the women who live there. It has been used as a theme song for sports teams, and it remains a popular song at sporting events to this day.

36. Baby Face – Jan Garber / Ben Selvin / “Whispering” Jack Smith

“Baby Face” was written by Harry Akst and Benny Davis in 1926. It became a hit for a number of artists, including Jan Garber, Ben Selvin, and “Whispering” Jack Smith. The song’s catchy melody and upbeat lyrics made it a favorite among dancers during the Roaring Twenties. The song tells the story of a man who falls in love with a woman after seeing her smile. It has since become a jazz standard and has been recorded by many artists.

37. Dinah – Ethel Waters / Cliff Edwards/ Revelers

“Dinah” was written by Harry Akst, Sam M. Lewis, and Joe Young in 1925. The song became a hit for Ethel Waters, Cliff Edwards, and the Revelers. Its catchy melody and playful lyrics made it a favorite among jazz musicians and fans. The song’s lyrics describe a man’s love for a woman named Dinah, and it has been recorded by many artists over the years.

38. My Man – Fanny Brice

“My Man” was written by Maurice Yvain, Jacques Charles, and Channing Pollock in 1921. The song became a hit for Fanny Brice in 1921 and has been recorded by many artists since. The song’s lyrics describe a woman’s love for her man and the pain she feels when he is away. It has been described as a quintessential torch song and is known for its emotional power and heartbreaking lyrics.

39. When My Baby Smiles At Me – Ted Lewis

“When My Baby Smiles at Me” was written by Ted Lewis, Andrew B. Sterling, and Bill Munro in 1920. The song became a hit for Ted Lewis and has been recorded by many artists since. Its upbeat melody and playful lyrics made it a popular dance song during the Roaring Twenties. The song’s lyrics describe a man’s love for his woman and the joy he feels when she smiles at him.

40. Some Of These Days (1927 Version) – Sophie Tucker

“Some of These Days” was written by Shelton Brooks in 1910. The song became a hit for Sophie Tucker in 1926 and has been recorded by many artists since. The song’s lively melody and catchy lyrics made it a favorite among jazz musicians and fans. The song’s lyrics describe a woman’s confidence in her ability to find love and happiness, even if it takes time. It has since become a jazz standard and is known for its upbeat energy and infectious rhythm.

41. Am I Blue – Ethel Waters / Libby Holman / Annette Hanshaw

“Am I Blue” is a classic torch song that has been interpreted by many legendary singers throughout the decades. Ethel Waters, Libby Holman, and Annette Hanshaw are some of the most notable artists who have recorded their own versions of the song. The tune was written by Harry Akst and Grant Clarke and first introduced in the 1929 film, “On with the Show!” The lyrics are poignant and melancholic, capturing the feeling of heartbreak and despair that often comes with lost love. The song’s opening lines, “Am I blue? Am I blue? Ain’t these tears, in these eyes tellin’ you?” immediately set the tone for the emotional journey that follows.

42. April Showers – Al Jolson / Paul Whiteman

“April Showers” is an upbeat and lively tune that is often associated with the 1920s era of jazz and swing. Al Jolson and Paul Whiteman are two of the most prominent musicians who have recorded the song, which was written by Louis Silvers and B.G. DeSylva. The song’s lyrics and melody evoke feelings of hope and optimism, celebrating the joy of new beginnings and the promise of brighter days ahead. The song’s refrain, “When April showers may come your way, they bring the flowers that bloom in May,” is a testament to the power of perseverance and the beauty that can come from difficult times. Overall, “April Showers” is a quintessential example of the joyful spirit and exuberant energy that defined the jazz age.

43. I’ve Found A New Baby – Ted Lewis / Ethel Waters

“I’ve Found a New Baby” is a jazz standard that has been recorded by many artists over the years, including Ted Lewis and Ethel Waters. The song was composed by Jack Palmer and Spencer Williams in 1926 and has become known for its catchy melody and upbeat tempo. The lyrics celebrate the joy of finding a new love and the excitement that comes with exploring a new relationship. Both Lewis and Waters bring their own unique style and interpretation to the song, with Lewis’s high-energy performance on clarinet and Waters’s smooth, sultry vocals.

44. Heebie Jeebies – Louis Armstrong

“Heebie Jeebies” is a classic jazz tune that was made famous by Louis Armstrong and his Hot Five in 1926. The song’s unique scatting vocals and rhythmic syncopation make it a standout example of early jazz music. Armstrong’s legendary trumpet playing is also on full display in the song, with his virtuosic solos and improvisation. The lyrics tell the humorous story of a man who becomes so overwhelmed by his love interest that he gets the “heebie-jeebies,” or feelings of anxiety and nervousness. The song’s joyful energy and playful lyrics make it a beloved classic in the jazz canon.

45. I Ain’t Got Nobody – Marion Harris / Sophie Tucker / Bessie Smith

“I Ain’t Got Nobody” is a blues standard that has been covered by several prominent singers, including Marion Harris, Sophie Tucker, and Bessie Smith. The song was originally composed by Spencer Williams in 1915 and has since become a staple in the blues repertoire. The lyrics tell the story of a person who has lost their love and is now alone, lamenting their loneliness and sorrow. The song’s simple melody and repetitive chorus make it an easily recognizable and timeless classic in the blues genre.

46. Valencia – Paul Whiteman / Ben Selvin

“Valencia” is a popular Spanish dance tune that was popularized in the United States by Paul Whiteman and Ben Selvin in the 1920s. The song’s catchy melody and lively rhythm make it a popular choice for dance parties and celebrations. The song’s instrumentation features a variety of Spanish-inspired instruments, such as the guitar and castanets, which create a festive and upbeat atmosphere.

47. Corrine Corrina – Bo Carter

“Corrine Corrina” is a blues standard that was originally recorded by Bo Carter in 1928. The song has since been covered by several artists, including Bob Dylan and Eric Clapton. The lyrics tell the story of a man who has lost his love, Corrine, and is now searching for her. The song’s simple melody and repetitive chorus make it a memorable and easily recognizable classic in the blues genre.

48. Wildwood Flower – Carter Family

“Wildwood Flower” is a folk song that was made famous by the Carter Family in the 1920s. The song’s simple melody and heartfelt lyrics have made it a beloved classic in the folk canon. The lyrics tell the story of a person who is pining for their lost love, with the wildwood flower serving as a symbol of their longing and sorrow. The Carter Family’s tight harmonies and understated instrumentation give the song a haunting beauty that has stood the test of time.

49. Singin’ The Blues – Frankie Trumbauer

“Singin’ the Blues” is a jazz standard that was popularized by Frankie Trumbauer and his Orchestra in 1927. The song features Bix Beiderbecke on cornet, whose lyrical playing and innovative solos helped to establish him as one of the greatest jazz musicians of his time. The song’s simple melody and catchy chorus make it an enduring classic in the jazz canon, with its themes of love and heartbreak resonating with audiences for generations.

50. Nobody Knows You When You’re Down And out – Bessie Smith

“Nobody Knows You When You’re Down and Out” is a blues standard that was recorded by Bessie Smith in 1929. The song’s lyrics speak to the hardships of life and the ways in which people can turn their backs on you when you’re in need. Smith’s powerful vocals and emotive delivery make the song a poignant reminder of the struggles that many people faced during the Great Depression.

51. Pony Blues – Charley Patton

“Pony Blues” is a Delta blues classic that was recorded by Charley Patton in 1929. The song’s driving rhythm and raw, expressive vocals make it a standout example of the Mississippi Delta blues style. The lyrics tell the story of a man who has lost his woman and is now wandering the countryside in search of her. The song’s haunting melody and intense emotional power make it a seminal example of early blues music.

52. Always – Vincent Lopez / George Olsen / Henry Burr / Nick Lucas

“Always” is a popular song that was composed by Irving Berlin in 1925. The song has since become a beloved classic in the American songbook, with its simple, romantic lyrics and lilting melody making it a favorite of crooners and big band orchestras alike. The song has been recorded by a variety of artists over the years, including Vincent Lopez, George Olsen, Henry Burr, and Nick Lucas.

53. I’ll See You In My Dreams – Isham Jones / Marion Harris

“I’ll See You In My Dreams” is a popular song that was composed by Isham Jones in 1924. The song’s wistful lyrics and sweet melody have made it a popular choice for romantic ballads and slow dances. The song has been recorded by several prominent artists, including Marion Harris, who had a hit with the song in 1925. The song’s nostalgic themes and sentimental lyrics have helped to cement its status as a beloved classic in the American songbook.

54. Singin’ In The Rain – Cliff Edwards / Earl Burtnett

“Singin’ in the Rain” is a classic song from the 1929 musical film “The Hollywood Revue of 1929”. The song was originally performed by Cliff Edwards, who played the character of “Ukulele Ike” in the film. The song has since become a beloved classic, with its joyful lyrics and catchy melody making it a perennial favorite. The song has been covered by numerous artists over the years, and has been featured in several films and television shows.

55. Tip Toe Through The Tulips – Nick Lucas

“Tip Toe Through the Tulips” is a popular song that was first recorded by Nick Lucas in 1929. The song’s whimsical lyrics and playful melody have made it a favorite of audiences of all ages, with its lightheartedness and sense of fun making it a perfect choice for movies and television shows. The song has been covered by several artists over the years, including Tiny Tim, who had a hit with the song in the 1960s.

56. I’m Looking Over A Four Leaf Clover – Nick Lucas / Ben Bernie

“I’m Looking Over a Four Leaf Clover” is a popular song that was first recorded by Nick Lucas in 1927. The song’s catchy melody and upbeat lyrics have made it a favorite of audiences for decades, with its infectious energy and optimism making it a perfect choice for sing-alongs and parties. The song has been covered by several artists over the years, including Ben Bernie, whose version of the song was a hit in 1928.

57. Let’s Do It (Let’s Fall In Love) – Dorsey Brothers Orchestra (Bing Crosby)

“Let’s Do It (Let’s Fall in Love)” is a popular song that was first recorded by the Dorsey Brothers Orchestra in 1928, with vocals by Bing Crosby. The song’s witty lyrics and upbeat melody have made it a beloved classic in the American songbook, with its themes of love and romance resonating with audiences of all ages. The song has been covered by several artists over the years, and has been featured in several films and television shows.

58. I Wanna Be Loved By You – Helen Kane

“I Wanna Be Loved By You” is a popular song that was first recorded by Helen Kane in 1928. The song’s playful lyrics and flirty melody have made it a favorite of audiences for decades, with its infectious charm and catchy chorus making it a perfect choice for romantic comedies and musicals. The song has been covered by several artists over the years, and has been featured in several films and television shows.

59. Bill – Helen Morgan

“Bill” is a popular song that was first introduced in the 1927 musical “Show Boat”. The song’s poignant lyrics and haunting melody have made it a beloved classic, with its themes of love and loss resonating with audiences for decades. The song has been covered by several artists over the years, including Helen Morgan, whose version of the song became a hit in 1928. The song has since become a staple of the American songbook, with its emotional power and evocative lyrics making it a timeless classic.

60. East St. Louis Toodle-oo – Duke Ellington

“East St. Louis Toodle-oo” is a classic jazz composition by the Duke Ellington Orchestra. It was one of their earliest hits and remains a staple of their repertoire to this day. The song features a distinctive, bluesy melody played on muted trumpets and trombones, with a driving rhythm section and the occasional solo from various members of the band. The title refers to East St. Louis, a city in Illinois just across the Mississippi River from St. Louis, Missouri, where Ellington and his band were performing regularly at the time. The song’s catchy melody and infectious beat have made it a favorite among jazz enthusiasts for nearly a century.

61. T’Ain’t Nobody’s Biz-ness If I Do – Bessie Smith

“T’Ain’t Nobody’s Biz-ness If I Do” is a classic blues song famously recorded by Bessie Smith. The song’s lyrics speak to a defiant spirit, insisting that the singer’s personal affairs are nobody else’s business. Smith’s powerful vocals, backed by a simple but effective blues arrangement, make for a memorable performance that has stood the test of time. The song has been covered by countless artists over the years, including Billie Holiday, Otis Spann, and Bonnie Raitt, among others, and remains a beloved classic of the blues repertoire.

62. Walk Right In – Cannon’s Jug Stompers

“Walk Right In” is a classic folk-blues song originally recorded by Cannon’s Jug Stompers. The song features a catchy melody played on banjo, harmonica, and jug, with witty lyrics that tell the story of a man trying to impress a woman. The song was a hit for the group in the 1920s and has since been covered by a wide range of artists, including The Rooftop Singers, who had a #1 hit with the song in 1963. The song’s upbeat tempo and infectious melody make it a favorite among fans of traditional American music.

63. Ida, Sweet As Apple Cider – Red Nichols

“Ida, Sweet As Apple Cider” is a classic jazz standard recorded by Red Nichols and His Five Pennies. The song features a playful melody played by Nichols’ trumpet and a driving rhythm section that swings throughout. The song’s lyrics celebrate the singer’s love for his girlfriend, Ida, and describe her as sweet as apple cider. The song was a hit in the 1920s and has since become a jazz standard, recorded by numerous artists over the years.

64. It Ain’t Gonna Rain No Mo’ – Wendell Hall

“It Ain’t Gonna Rain No Mo'” is a classic American folk song recorded by Wendell Hall. The song features a simple melody played on ukulele, with humorous lyrics that describe the singer’s relief that the rain has finally stopped. The song has been covered by a wide range of artists over the years and has become a beloved standard of the folk repertoire.

65. Side By Side – Paul Whiteman / Nick Lucas

“Side By Side” is a classic popular song recorded by Paul Whiteman and Nick Lucas. The song features a sentimental melody and lyrics that describe the singer’s desire to always be by his loved one’s side. The song was a hit in the 1920s and has since become a standard of the popular music repertoire, recorded by numerous artists over the years.

66. Somebody Stole My Gal – Ted Weems

“Somebody Stole My Gal” is a classic popular song recorded by Ted Weems and His Orchestra. The song features a catchy melody played by Weems’ clarinet and a driving rhythm section that swings throughout. The song’s lyrics describe the singer’s heartbreak after his girlfriend is stolen by another man. The song was a hit in the 1920s and has since become a popular standard of the jazz and swing repertoire.

67. Three O’Clock In The Morning – Paul Whiteman / Frank Crumit

“Three O’Clock In The Morning” was a popular song composed by Julián Robledo in 1919, which became a hit for Paul Whiteman and His Orchestra in 1922. The song is a romantic ballad that describes a moment of contemplation and longing at the late hour of 3 am. The melody is gentle and soothing, and the lyrics convey a feeling of nostalgia and yearning. The Whiteman version features Frank Crumit on vocals, who sings with a gentle, almost whisper-like tone that enhances the intimate and dreamy atmosphere of the song. The tune quickly became a popular standard, and many other artists recorded their own versions of it in the following years.

68. Carolina In The Morning – Van & Schenck / Marion Harris

“Carolina In The Morning” is a cheerful song that celebrates the beauty of a sunny morning in the South. The song was written by Walter Donaldson and Gus Kahn in 1922 and was first recorded by Van & Schenck. The tune’s upbeat rhythm and catchy melody make it an enduring classic of the Roaring Twenties. Marion Harris’s recording of the song in 1923 was also quite successful, and it became one of her signature tunes. The lyrics describe the joys of a morning walk in the countryside, with the singer admiring the natural beauty of the landscape and feeling grateful for life’s simple pleasures. The tune’s optimistic and carefree mood captured the spirit of the Jazz Age and remains an upbeat favorite today.

69. Blue Skies – Ben Selvin / George Olsen / Vincent Lopez

“Blue Skies” is a classic song from the 1920s that has become a beloved standard over the years. Written by Irving Berlin, the song was first recorded by the Ben Selvin Orchestra in 1926, and it quickly became a hit. The song features a simple melody and optimistic lyrics about looking forward to sunny days and blue skies ahead. Over the years, “Blue Skies” has been covered by many artists, including Frank Sinatra, Ella Fitzgerald, and Willie Nelson, and has become a beloved classic.

70. If You Knew Susie – Eddie Cantor / Cliff Edwards

“If You Knew Susie” is a popular song from the 1920s, written by Buddy DeSylva and Joseph Meyer, and made famous by Eddie Cantor and Cliff Edwards. The song is a fun, upbeat tune that tells the story of a man who is trying to convince his friends that he knows a woman named Susie, but they don’t believe him. The song features playful lyrics and a catchy melody that has made it a favorite of audiences for nearly a century.

71. Little Pal – Al Jolson

“Little Pal” is a sentimental ballad performed by Al Jolson in the 1920s. The song tells the story of a father who is comforting his son after his mother has died, promising to always be there for him and to be his “little pal.” The song features Jolson’s distinctive vocals and a simple, yet touching melody that has made it a favorite of parents and children for many years.

72. The Birth Of The Blues – Paul Whiteman / Harry Richman

“The Birth of the Blues” is a classic jazz tune from the 1920s, written by Ray Henderson, Buddy DeSylva, and Lew Brown, and performed by Paul Whiteman and Harry Richman. The song features a swinging melody and clever lyrics about the origins of the blues, including references to African-American culture and early jazz music. The song has been covered by many artists over the years, including Ella Fitzgerald and Louis Armstrong, and remains a beloved standard of the jazz repertoire.

73. Aggravatin’ Papa – Marion Harris / Bessie Smith / Sophie Tucker

“Aggravatin’ Papa” is a classic blues tune from the 1920s, written by Roy Turk and J. Russel Robinson, and performed by Marion Harris, Bessie Smith, and Sophie Tucker. The song features a sassy, confident vocal performance and a catchy melody, with lyrics about a woman who is tired of her man’s aggravating behavior and ready to stand up for herself. The song has become a favorite of blues and jazz fans over the years, and has been covered by many artists in a variety of styles.

74. Empty Bed Blues – Bessie Smith

“Empty Bed Blues” is a classic blues song performed by Bessie Smith in 1928. The song features Smith’s powerful vocals and a haunting melody, with lyrics about a woman who has been left alone in bed by her man. The song is a raw and emotional expression of the pain and loneliness of being abandoned, and Smith’s performance has made it a landmark of the blues genre.

75. Love Me Or Leave Me – Ruth Etting

“Love Me or Leave Me” is a popular song from the 1920s, written by Walter Donaldson and Gus Kahn, and performed by Ruth Etting. The song features a catchy melody and lyrics about a woman who is tired of being toyed with by her lover and demands that he either commit to her or leave her alone. Etting’s smooth, silky vocals and dynamic range make the song a timeless classic.

76. Lovesick Blues – Emmett Miller & His Georgia Crackers

“Lovesick Blues” is a country blues song originally performed by Emmett Miller & His Georgia Crackers in 1925. The song features Miller’s yodeling vocals and a lively, upbeat melody, with lyrics about a man who is heartbroken over a lost love. The song has since been covered by many artists, including Hank Williams, and has become a beloved standard of country music.

77. Someone To Watch Over Me – Gertrude Lawrence / George Olsen

“Someone to Watch Over Me” is a classic song from the 1920s, written by George and Ira Gershwin, and performed by Gertrude Lawrence and George Olsen. The song features a romantic melody and lyrics about a person who is longing for someone to protect and care for them. The song has since become a standard of the American Songbook, with covers by many artists, including Ella Fitzgerald and Frank Sinatra.

78. Muskrat Ramble – Louis Armstrong

“Muskrat Ramble” is a jazz standard performed by Louis Armstrong and his Hot Five in 1926. The song features lively instrumentation, with Armstrong’s trumpet leading the way, and catchy lyrics about a muskrat who loves to dance. The song has since become a jazz classic, with covers by many artists, including Ella Fitzgerald and Wynton Marsalis.

79. Ain’t We Got Fun – Van & Schenck

“Ain’t We Got Fun” is a popular song from the 1920s, performed by Van & Schenck. The song features a jaunty melody and lyrics about finding joy in simple pleasures, even in the midst of difficult times. The song was a hit during the Great Depression and has since become a beloved standard of the American Songbook.

80. Me And My Shadow – “Whispering” Jack Smith / Nat Shilkret

“Me and My Shadow” is a classic song from the 1920s, performed by “Whispering” Jack Smith and Nat Shilkret. The song features a haunting melody and lyrics about the companionship of one’s own shadow, even in the darkest moments. The song has since been covered by many artists, including Frank Sinatra, and has become a beloved standard of the American Songbook.

81. Swingin’ Down The Lane – Isham Jones / Ben Bernie

“Swingin’ Down The Lane” is a popular song from the 1920s, written by Isham Jones and Gus Kahn, and performed by Ben Bernie. The song features a swinging melody and lyrics about a couple in love taking a stroll down a country lane. The song has since become a classic of the American Songbook, with covers by many artists, including Ella Fitzgerald and Bing Crosby.

82. When The Red, Red Robin Comes Bob-Bob-Bobbin’ Along – Al Jolson

“When The Red, Red Robin Comes Bob-Bob-Bobbin’ Along” is a classic song from the 1920s, performed by Al Jolson. The song features a joyful melody and lyrics about the arrival of spring and the happiness that comes with it. The song has since become a beloved standard of the American Songbook, with covers by many artists, including Bing Crosby and Doris Day.

83. Charmaine – Guy Lombardo

“Charmaine” by Guy Lombardo is a classic ballad that was originally composed by Erno Rapee and Lew Pollack for the 1926 silent film “What Price Glory?” The song quickly gained popularity and became a timeless favorite, with Lombardo’s version being one of the most well-known. The romantic melody features a hauntingly beautiful violin solo and tender lyrics about a love that is lost but never forgotten. Lombardo’s smooth vocals and the dreamy orchestration add to the nostalgic atmosphere of the song, evoking a sense of longing and melancholy. “Charmaine” is a perfect representation of the romantic ballads of the 1920s, and it continues to be a beloved classic today.

84. Fare You Well, Old Joe Clark – Fiddlin’ John Carson

“Fare You Well, Old Joe Clark” by Fiddlin’ John Carson is a traditional American folk song that dates back to the 1800s. Carson’s version is a lively and upbeat interpretation of the song, featuring his signature fiddle playing and twangy vocals. The lyrics tell the story of Old Joe Clark, a legendary mountain man who lived in the Appalachian region and was known for his hard work and lively personality. The song is a celebration of his life and legacy, with the chorus urging him to “fare you well.” Carson’s rendition of “Fare You Well, Old Joe Clark” is a testament to the enduring power of traditional folk music, and his energetic performance captures the joy and spirit of the genre.

85. Turkey In The Straw – Gid Tanner & His Skillet Lickers

“Turkey in the Straw” by Gid Tanner & His Skillet Lickers is a classic American folk song with a lively and infectious melody. The upbeat fiddle-driven tune is often associated with traditional square dancing and is a favorite at barn dances and other social gatherings. Gid Tanner’s version of the song is particularly notable for its fast tempo and energetic performance, which perfectly captures the festive spirit of the piece.

86. Who’s Sorry Now – Isham Jones / Marion Harris

“Who’s Sorry Now” by Isham Jones and Marion Harris is a poignant ballad that tells the story of a lost love. The melancholy lyrics, paired with Jones’ elegant orchestration and Harris’ soulful vocals, make for a powerful and emotive performance. The song was a huge hit in the 1920s, and it remains a beloved classic today.

87. The Sidewalks Of New York – Nat Shilkret

“The Sidewalks of New York” by Nat Shilkret is a nostalgic ode to the streets of New York City. The cheerful melody and upbeat lyrics celebrate the hustle and bustle of urban life and the city’s diverse communities. Shilkret’s sweet and mellow rendition of the song perfectly captures the wistful sentiment of the lyrics, making it a timeless favorite.

88. Sleep – Fred Waring’s Pennsylvanians

“Sleep” is a lullaby composed by Earl Burtnett and originally recorded by Fred Waring’s Pennsylvanians in 1923. The song features soothing lyrics that encourage the listener to drift off to sleep, with Waring’s Pennsylvanians providing a gentle accompaniment of harmonies and instruments. The song became a popular choice for parents to play for their children at bedtime, and it remains a classic lullaby to this day.

89. Honey – Rudy Vallee

“Honey” is a love song written by Seymour Simons and Haven Gillespie and popularized by Rudy Vallee in 1928. The song features a catchy melody and romantic lyrics that express the singer’s affection for his sweetheart, who he affectionately calls “Honey.” Vallee’s smooth vocals and the accompanying orchestra make the song a classic example of 1920s jazz-pop.

90. Margie – Eddie Cantor / Ted Lewis

“Margie” is a popular song from 1920, composed by Con Conrad and Benny Davis, and recorded by Eddie Cantor and Ted Lewis. The song features an upbeat melody and lyrics that celebrate the singer’s love for a woman named Margie. Cantor’s and Lewis’s renditions of the song are both lively and joyful, with catchy instrumentation and playful vocals.

91. Parade Of The Wooden Soldiers – Paul Whiteman / Vincent Lopez

“Parade of the Wooden Soldiers” is an instrumental piece composed by Leon Jessel in 1897, but popularized by orchestras such as Paul Whiteman and Vincent Lopez in the 1920s. The song is a lively march featuring woodwind and percussion instruments, with a memorable melody that evokes images of a toy soldier parade. The song has become a holiday classic, often played during Christmas and other festive occasions.

92. Sleepy Time Gal – Ben Bernie / Gene Austin / Nick Lucas

“Sleepy Time Gal” is a popular song from 1925, composed by Ange Lorenzo, Richard Whiting, and Joseph Reed. The song features gentle lyrics that encourage the listener to rest and dream peacefully, with mellow vocals and soft instrumentation provided by singers such as Ben Bernie, Gene Austin, and Nick Lucas. The song has become a standard lullaby, often played at bedtime or during moments of relaxation.

93. All Alone – Al Jolson / John McCormack / Paul Whiteman

“All Alone” is a melancholic ballad from 1924, composed by Irving Berlin, and recorded by Al Jolson, John McCormack, and Paul Whiteman. The song features tender lyrics that express the loneliness and heartbreak of being separated from a loved one. Jolson’s powerful vocals and Whiteman’s sweet orchestra arrangement make for a poignant rendition of the song that captures its emotional depth.

94. Five Foot Two, Eyes Of Blue – Gene Austin

“Five Foot Two, Eyes Of Blue” is a popular song from 1925, written by Ray Henderson, Sam Lewis, and Joe Young, and recorded by Gene Austin. The song features a bouncy, upbeat melody and playful lyrics that describe a charming young woman who is just five feet two inches tall. Austin’s lively vocals and the accompanying ukulele and piano create a cheerful atmosphere that makes the song a classic of 1920s pop.

95. Among My Souvenirs – Paul Whiteman / Ben Selvin

“Among My Souvenirs” is a wistful ballad from 1927, composed by Horatio Nicholls and Edgar Leslie, and recorded by Paul Whiteman and Ben Selvin. The song features nostalgic lyrics that describe the memories of a lost love, and the pain of looking back on happier times. The melancholic vocals and the gentle accompaniment of Whiteman’s orchestra create a tender and emotional atmosphere that captures the song’s poignant sentiment.

96. The Brakeman’s Blues – Jimmie Rodgers

“The Brakeman’s Blues” is a blues song from 1928, written and recorded by Jimmie Rodgers. The song features lyrics that describe the hard life of a brakeman on a train, working long hours and struggling to make ends meet. Rodgers’ raw, emotive vocals and the accompanying guitar and harmonica create a powerful and authentic rendition of the blues, capturing the pain and hardship of the working-class experience.

97. Shake That Thing – Ethel Waters / Papa Charlie Jackson

“Shake That Thing” is an upbeat and lively song from 1925, recorded by Ethel Waters and Papa Charlie Jackson. The song features lyrics that encourage the listener to let loose and dance, with a catchy melody and infectious rhythm that make it impossible to resist. Waters’ energetic vocals and Jackson’s bluesy guitar playing make for a lively and exciting rendition of the song that captures the spirit of 1920s dance music.

98. James Alley Blues – Rabbit Brown

“James Alley Blues” is a folk-blues song from 1927, performed by Rabbit Brown. The song features raw, emotive vocals and a simple acoustic guitar accompaniment, creating an authentic and unvarnished rendition of the blues. The lyrics describe the hard times and struggles of life in New Orleans, with a sense of resignation and acceptance that captures the resilience of the working-class experience.

99. Way Down Yonder In New Orleans – Peerless Quartet / Blossom Seeley

“Way Down Yonder In New Orleans” is a jazz standard from 1922, recorded by the Peerless Quartet and Blossom Seeley. The song features a catchy melody and upbeat lyrics that celebrate the vibrant energy and cultural richness of New Orleans. The quartet’s tight harmonies and Seeley’s lively vocals create a joyful and infectious rendition of the song that captures the spirit of early jazz.

100. Big Butter And Egg Man – Louis Armstrong (May Alix)

“Big Butter and Egg Man” is a classic jazz tune from 1926, recorded by Louis Armstrong (with May Alix on vocals). The song features a swinging melody and playful lyrics that describe a wealthy man who can afford to buy all the best things in life. Armstrong’s virtuosic trumpet playing and Alix’s sassy vocals create a lively and entertaining rendition of the song that captures the fun and exuberance of 1920s jazz. The song is a testament to Armstrong’s skill as both a musician and a showman, and remains a beloved classic of the genre.