100 Greatest  Popular  Songs Of The  20s
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Criteria: These songs were chosen and ranked according to their initial and lasting popularity and also on their impact and influence on the course of musical history. At that time most songs were recorded by many different artists, so we have listed more than one version of each song on the majority of the entries. The most significant version of the song is the one by the first artist that is listed.
Popular Songs Of The 1920s   1. Swanee - Al Jolson   2. West End Blues - Louis Armstrong   3. Rhapsody In Blue - Paul Whiteman featuring George Gershwin   4. Ain't Misbehavin' - Fats Waller / Louis Armstrong   5. T For Texas (Blue Yodel #1) - Jimmie Rodgers   6. In The Jailhouse Now - Jimmie Rodgers   7. The Prisoner's Song - Vernon Dalhart   8. The St. Louis Blues - Bessie Smith / Marion Harris   9. Ol' Man River - Paul Robeson / Al Jolson 10. Makin' Whoopee - Eddie Cantor/ Paul Whiteman (Bing Crosby) 11. Crazy Blues - Mamie Smith 12. My Blue Heaven - Gene Austin / Paul Whiteman 13. Sonny Boy - Al Jolson 14. Dardanella - Ben Selvin 15. It Had To Be You - Isham Jones / Marion Harris 16. Pine Top's Boogie Woogie - Pine Top Smith 17. Whispering - Paul Whiteman 18. My Mammy - Al Jolson / Paul Whiteman 19. Down Hearted Blues - Bessie Smith 20. Charleston - Arthur Gibbs /Paul Whiteman 21. Black And Tan Fantasy - Duke Ellington 22. See See Rider Blues - Ma Rainey 23. Statesboro Blues - Blind Willie McTell 24. Matchbox Blues - Blind Lemon Jefferson 25. Bye Bye, Blackbird - Gene Austin / Nick Lucas 26. King Porter Stomp - Fletcher Henderson / Jelly Roll Morton 27. California, Here I Come! - Al Jolson 28. In A Mist - Bix Beiderbecke 29. Waiting For A Train - Jimmie Rodgers 30. Louise - Maurice Chevalier 31. Star Dust - Hoagy Carmichael 32. Yes! We Have No Bananas - Billy Jones / Ben Selvin 33. Yes Sir That's My Baby - Gene Austin / Blossom Seeley / Ben Bernie 34. Toot Toot Tootsie (Goo'Bye) - Al Jolson 35. Sweet Georgia Brown - Ben Bernie / Isham Jones / Ethel Waters 36. Baby Face - Jan Garber / Ben Selvin / "Whispering" Jack Smith 37. Dinah - Ethel Waters / Cliff Edwards/ Revelers 38. My Man - Fanny Brice 39. When My Baby Smiles At Me - Ted Lewis 40. Some Of These Days (1927 Version) - Sophie Tucker 41. Am I Blue - Ethel Waters / Libby Holman / Annette Hanshaw 42. April Showers - Al Jolson / Paul Whiteman 43. I've Found A New Baby - Ted Lewis / Ethel Waters 44. Heebie Jeebies - Louis Armstrong 45. I Ain't Got Nobody - Marion Harris / Sophie Tucker / Bessie Smith 46. Valencia - Paul Whiteman / Ben Selvin 47. Corrine Corrina - Bo Carter 48. Wildwood Flower - Carter Family 49. Singin' The Blues - Frankie Trumbauer 50. Nobody Knows You When You're Down And out - Bessie Smith 51. Pony Blues - Charley Patton 52. Always - Vincent Lopez / George Olsen / Henry Burr / Nick Lucas 53. I'll See You In My Dreams - Isham Jones / Marion Harris 54. Singin' In The Rain - Cliff Edwards / Earl Burtnett 55. Tip Toe Through The Tulips - Nick Lucas 56. I'm Looking Over A Four Leaf Clover - Nick Lucas / Ben Bernie 57. Let's Do It (Let's Fall In Love) - Dorsey Brothers Orchestra (Bing Crosby) 58. I Wanna Be Loved By You - Helen Kane 59. Bill - Helen Morgan 60. East St. Louis Toodle-oo - Duke Ellington 61. T'Ain't Nobody's Biz-ness If I Do - Bessie Smith 62. Walk Right In - Cannon's Jug Stompers 63. Ida, Sweet As Apple Cider - Red Nichols 64. It Ain't Gonna Rain No Mo' - Wendell Hall 65. Side By Side - Paul Whiteman / Nick Lucas 66. Somebody Stole My Gal - Ted Weems 67. Three O'Clock In The Morning - Paul Whiteman / Frank Crumit 68. Carolina In The Morning - Van & Schenck / Marion Harris 69. Blue Skies - Ben Selvin / George Olsen / Vincent Lopez 70. If You Knew Susie - Eddie Cantor / Cliff Edwards 71. Little Pal - Al Jolson 72. The Birth Of The Blues - Paul Whiteman / Harry Richman 73. Aggravatin' Papa - Marion Harris / Bessie Smith / Sophie Tucker 74. Empty Bed Blues - Bessie Smith 75. Love Me Or Leave Me - Ruth Etting 76. Lovesick Blues - Emmett Miller & His Georgia Crackers 77. Someone To Watch Over Me - Gertrude Lawrence / George Olsen 78. Muskrat Ramble - Louis Armstrong 79. Ain't We Got Fun - Van & Schenck 80. Me And My Shadow - "Whispering" Jack Smith / Nat Shilkret 81. Swingin' Down The Lane - Isham Jones / Ben Bernie 82. When The Red, Red Robin Comes Bob-Bob-Bobbin' Along - Al Jolson 83. Charmaine - Guy Lombardo 84. Fare You Well, Old Joe Clark - Fiddlin' John Carson 85. Turkey In The Straw - Gid Tanner & His Skillet Lickers 86. Who's Sorry Now - Isham Jones / Marion Harris 87. The Sidewalks Of New York - Nat Shilkret 88. Sleep - Fred Waring's Pennsylvanians 89. Honey - Rudy Vallee 90. Margie - Eddie Cantor / Ted Lewis 91. Parade Of The Wooden Soldiers - Paul Whiteman / Vincent Lopez 92. Sleepy Time Gal - Ben Bernie / Gene Austin / Nick Lucas 93. All Alone - Al Jolson / John McCormack / Paul Whiteman 94. Five Foot Two, Eyes Of Blue - Gene Austin 95. Among My Souvenirs - Paul Whiteman / Ben Selvin 96. The Brakeman's Blues - Jimmie Rodgers 97. Shake That Thing - Ethel Waters / Papa Charlie Jackson 98. James Alley Blues - Rabbit Brown 99. Way Down Yonder In New Orleans - Peerless Quartet / Blossom Seeley 100. Big Butter And Egg Man - Louis Armstrong (May Alix)