Top 100 Songs Of The 20s

Picture of a 1920's Phonograph Player
Picture of a 1920’s Phonograph Player

Do you know which songs of the twenties were the most popular? Here is where the top 100 songs of the 20’s will help you. Many people growing up during this decade the economy was very good during these years of 1920-1929 and were known as the “Roaring Twenties”. The Charleston becomes the dance craze of the decade and went to number 1 in 1924.

People were investing in the stock market and earning money like it had no end. The end did come on “Black Thursday” on October 29, 1929, when the stock market crashed big time. Everyone lost lots of money and many lost everything they had.

During this time, people were listening to the radio and having lots of fun remembering artists like Paul Whiteman, Eddie Cantor, Al Jolson, Ben Selvin, Isham Jones, and Gene Austin as they kept recording great hits during this fabulous decade.

In unrelated news, now there is a way to preserve your vinyl records and convert them to the CD format. Click here for more information.

Paul Whiteman 1927
Paul Whiteman 1927

Interesting Facts of the 20’s

  • There were a total of 122 songs that peaked at the #1 position during this era.
  • The year of 1927 had the most songs on the list with 12.
  • All the songs on this list had to peak at the #1 position and stay at #1 for a minimum of 2 weeks.
  • Paul Whiteman had the most songs on the list with 23.
  • Paul Whiteman had the most #1 songs of this decade with 26. These songs spent a total of 112 weeks at the #1 position during this era.
  • For a song to be in the top 10, it had to be at #1 for 8 weeks.
  • For a Song to be in the top 40, it had to be at #1 for 5 weeks.
  • Both Al Jolson and Paul Whiteman had 3 songs in the top ten.
  • The biggest selling song of the decade was “The Prisoner’s Song” by Vernon Dalhart which sold over 7 million copies.
  • The most recorded song of this decade was Stardust in 1929,written by Hoagy Carmichael and Mitchell Parish as it’s number 3 on the list of most recorded songs of all time.
  • The song “The Prisoner’s Song” #3, recorded in 1926 by Vernon Dalhart, holds the title for longevity by staying on the charts for 32 weeks.

The Top 100 Songs 1920-1929

Picture of Al Jolson
Picture of Al Jolson

The list will be composed of the title, artist, peak weeks (), and year of release. Songs with an [I] denotes an instrumental hit.

Rank      Title / Artist / Peak Weeks() / Year of Release

  1. My Blue Heaven / Gene Austin (13) 1927
  2. Dardanella [I] / Ben Selvin (13) 1920
  3. The Prisoner’s Song / Vernon Dalhart (12) 1926
  4. Sonny Boy / Al Jolson (12) 1928
  5. Whispering [I] / Paul Whiteman (11) 1920
  6. April Showers / Al Jolson (11) 1922
  7. Valencia / Paul Whiteman (11) 1926
  8. Tip Toe Through The Tulips / Nick Lucas (10) 1929
  9. Swanee / Al Jolson (9) 1920
  10. Three O’Clock In The Morning [I] / Paul Whiteman (8) 1922
  11. Ramona / Gene Austin (8) 1928
  12. In A Little Spanish Town / Paul Whiteman (8) 1927
  13. Honey / Rudy Vallee (8) 1929
  14. When My Baby Smiles At Me / Ted Lewis (7) 1920
  15. Yes Sir! That’s My Baby / Gene Austin (7) 1925
  16. I’ll See You In My Dreams / Isham Jones (7) 1925
  17. Charmaine! / Guy Lambardo (7) 1927
  18. Carolina Moon / Gene Austin (7) 1929
  19. Parade Of The Wooden Soldiers [I] / Paul Whiteman (7) 1923
  20. It Ain’t Gonna Rain No Mo’ / Wendell Hall (6) 1924
  21. Wang Wang Blues [I] / Paul Whiteman (6) 1921
  22. My Angel / Paul Whiteman (6) 1928
  23. Swingin’ Down The Lane [I] / Isham Jones (6) 1923
  24. That Old Gang Of Mine / Billy Murray (6) 1923
  25. California, Here I Come / Al Jolson (6) 1924
  26. Mr. Gallagher And Mr. Shean / Gallagher & Shean (6) 1922
  27. Who? / George Olsen (6) 1926
  28. Wabash Blues [I] / Isham Jones (6) 1921
  29. Baby Face / Jan Garber (6) 1926
  30. Cherie [I] / Paul Whiteman (6) 1921
  31. Stumbling [I] / Paul Whiteman (6) 1922
  32. Hot Lips [I] / Paul Whiteman (6) 1922
  33. The Prisoner’s Song / Vernon Dalhart (5) 1925
  34. Memory Lane / Fred Waring (5) 1924
  35. Jeannie (I Dream Of Lilac Time) / Gene Austin (5) 1928
  36. It Had To Be You [I] / Isham Jones (5) 1924
  37. What’ll I Do? [I] / Paul Whiteman (5) 1924
  38. Song Of India [I] / Paul Whiteman (5) 1921
  39. Say It With Music [I] / Paul Whiteman (5) 1921
  40. Somebody Stole My Gal [I] / Ted Weems (5) 1924
  41. Sweet Georgia Brown / Ben Bernie (5) 1925
  42. Yes! We Have No Bananas / Billy Jones (5) 1923
  43. Margie / Eddie Cantor (5) 1921
  44. If You Knew Susie / Eddie Cantor (5) 1925
  45. Two Black Crows Parts 1 & 2 / Moran & Mack (5) 1927
  46. My Mammy [I] / Paul Whiteman (5) 1921
  47. Somebody Loves Me [I] / Paul Whiteman (5) 1924
  48. Some Of These Days / Sophie Tucker (5) 1927
  49. Sleep / Fred Waring (5) 1924
  50. All Alone / Al Jolson (5) 1925
  51. Angel Child / Al Jolson (5) 1922
  52. Me And My Shadow / Jack Smith (4) 1927
  53. Sleepy Time Gal / Ben Bernie (4) 1926
  54. Among My Souvenirs / Paul Whiteman (4) 1928
  55. Ain’t She Sweet? / Ben Bernie (4) 1927
  56. Down Hearted Blues / Bessie Smith (4) 1923
  57. The Wedding Of The Painted Doll / Leo Reisman (4) 1929
  58. The Birth Of The Blues / Paul Whiteman (4) 1926
  59. All By Myself / Ted Lewis (4) 1921
  60. Pagan Love Song / Bob Haring (4) 1929
  61. Toot Toot Tootsie / Al Jolson (4) 1923
  62. Manhattan [I] / Ben Selvin (4) 1925
  63. On The Alamo [I] / Isham Jones (4) 1922
  64. The Love Nest / John Steel (4) 1920
  65. Linger A While [I] / Paul Whiteman (4) 1924
  66. O-H-I-O / Al Jolson (4) 1921
  67. Ida, Sweet As Apple Cider / Red Nichols (3) 1927
  68. Russian Lullaby / Roger Wolfe Kahn (3) 1927
  69. Hold Me / Art Hickman (3) 1920
  70. Carolina In The Morning / Van & Schenck (3) 1923
  71. Tonight You Belong To Me / Gene Austin (3) 1927
  72. I Wonder What’s Become Of Sally? / Al Jolson (3) 1924
  73. Oh, How I Miss You Tonight [I] / Ben Selvin (3) 1925
  74. Singin’ In The Rain / Cliff Edwards (3) 1929
  75. Bye Bye, Blackbird / Gene Austin (3) 1926
  76. At Sundown / George Olsen (3) 1927
  77. Sweethearts On Parade / Guy Lombardo (3) 1929
  78. Ramona / Paul Whiteman (3) 1928
  79. Tea For Two / Marion Harris (3) 1925
  80. Little Pal / Al Jolson (3) 1929
  81. Dreamy Melody / Art Landry (3) 1923
  82. Love Sends A Little Gift Of Roses / Carl Fenton (3) 1923
  83. Always / George Olsen (3) 1926
  84. Look For The Silver Lining / Marion Harris (3) 1921
  85. Make Believe / Nora Bayes (3) 1921
  86. St. Louis Blues / Marion Harris (3) 1920
  87. All Alone [I] / Paul Whiteman (3) 1925
  88. Am I Blue? / Ethel Waters (2) 1929
  89. There’s A Rainbow Round My Shoulder / Al Jolson (2) 1928
  90. Yes! We Have No Bananas / Ben Selvin (2) 1923
  91. Spain / Isham Jones (2) 1924
  92. The Japanese Sandman [I] / Paul Whiteman (2) 1920
  93. Together / Paul Whiteman (2) 1928
  94. I’m Sitting On Top Of The World / Al Jolson (2) 1926
  95. A Precious Little Thing Called Love / George Olsen (2) 1929
  96. Breezin’ Along The Breeze / Johnny Marvin (2) 1926
  97. Blue Skies / Ben Selvin (2) 1927
  98. Mr. Gallagher And Mr. Shean / Earnest Hare & Billy Jones (2) 1922
  99. No, No, Nora / Eddie Cantor (2) 1923
  100. Do It Again [I] / Paul Whiteman (2) 1922

Go back to the top 100 songs of all time home page.

Back to Top