These are the top 100 songs from the 1920s according to Dave’s Music Database. Rankings are figured by combining sales figures, chart data, radio airplay, video airplay, streaming figures, awards, and appearances on best-of lists.
Check out other “songs of the decade” lists here.
1. Bessie Smith with Louis Armstrong “St. Louis Blues” (1925)
2. Al Jolson “Swanee” (1920)
3. Gene Austin “My Blue Heaven” (1927)
4. Thomas “Fats” Waller “Ain’t Misbehavin’” (1929)
5. Paul Whiteman “Whispering” (1920)
6. Al Jolson "April Showers” (1922)
7. Marion Harris “Tea for Two” (1925)
8. Vernon Dalhart “The Prisoner’s Song” (1925)
9. Ben Selvin “Dardanella” (1920)
10. Isham Jones “It Had to Be You” (1924)
11. Paul Whiteman with Bing Crosby “Ol’ Man River” (1928)
12. Cliff Edwards “I Can’t Give You Anything But Love” (1928)
13. George Olsen with Fran Frey, Bob Rice & Edward Joyce “Always” (1926)
14. Al Jolson “Sonny Boy” (1928)
15. Ben Selvin “Blue Skies” (1927)
16. Van & Schenck “Ain’t We Got Fun?” (1921)
17. Gertrude Lawrence “Someone to Watch Over Me” (1927)
18. Paul Whiteman” Three O’Clock in the Morning” (1922)
19. Ben Bernie “Sweet Georgia Brown” (1925)
20. Nick Lucas “Tip-Toe Thru the Tulips with Me” (1929)
21. Paul Whiteman with George Gershwin “Rhapsody in Blue” (1924)
22. Van & Schenck “Carolina in the Morning” (1923)
23. Gene Austin “My Melancholy Baby” (1928)
24. Al Jolson with Isham Jones “California, Here I Come” (1924)
25. Bessie Smith “Down Hearted Blues” (1923)
26. Gene Austin “Bye Bye, Blackbird” (1926)
27. Gene Austin with Billy Carpenter “Yes Sir! That’s My Baby” (1925)
28. Marion Harris “The Man I Love” (1928)
29. Paul Whiteman “My Mammy” (1921)
30. Cliff Edwards “Singin’ in the Rain” (1929)
31. Billy Jones “Yes! We Have No Bananas” (1923)
32. Eddie Cantor “If You Knew Susie Like I Know Susie” (1925)
33. Wendall Hall “It Ain’t Gonna Rain No Mo’” (1924)
34. Paul Whiteman with Franklyn Baur “Valencia (A Song of Spain)” (1926)
35. Ben Selvin “Manhattan” (1925)
36. Paul Whiteman “What’ll I Do?” (1924)
37. Eddie Cantor “Makin’ Whoopee” (1929)
38. Eddie Cantor “Margie” (1921)
39. Paul Whiteman “The Japanese Sandman” (1920)
40. Isham Jones with Ray Miller & Frank Bessinger “I’ll See You in My Dreams” (1925)
41. Ben Bernie with Scrappy Lambert & Billy Hillpot “Ain’t She Sweet?” (1927)
42. Paul Whiteman “Somebody Loves Me” (1924)
43. Arthur Gibbs & His Gang “Charleston” (1924)
44. Fanny Brice “My Man (Mon Homme)” (1922)
45. Gene Austin with Nat Shilkret & Viola Klaiss “Ramona” (1928)
46. Al Jolson “All Alone” (1925)
47. Paul Whiteman with Jack Fulton, Charles Gaylord, & Austin Young “The Birth of the Blues” (1926)
48. Al Jolson “Toot, Toot, Tootsie! (Goo’bye)” (1922)
49. Marion Harris “Look for the Silver Lining” (1921)
50. Whisperin’ Jack Smith “Me and My Shadow” (1927)
51. George Olsen “Who?” (1926)
52. Jan Garber with Benny Davis “Baby Face” (1926)
53. Ruth Etting “Love Me or Leave Me” (1929)
54. Henry Burr “My Buddy” (1922)
55. Isham Jones “Wabash Blues” (1921)
56. Ted Lewis & His Band “When My Baby Smiles at Me” (1920)
57. Ethel Waters “Am I Blue?” (1929)
58. Jimmie Rodgers “Blue Yodel #1 (T for Texas)” (1928)
59. Ray Miller & His Orchestra “The Sheik of Araby” (1922)
60. Ted Lewis “All by Myself” (1921)
61. Al Jolson “I’m Sitting on Top of the World” (1926)
62. Paul Whiteman “Wang Wang Blues” (1920)
63. Ted Weems “Somebody Stole My Gal” (1924)
64. Mamie Smith & Her Jazz Hounds “Crazy Blues” (1920)
65. Ben Selvin “Chicago (That Toddlin’ Town)” (1922)
66. Ed Gallagher & Al Shean “Mr. Gallagher and Mr. Shean – ‘Positively, Mr. Gallagher?’” (1922)
67. Guy Lombardo with Weston Vaughan “Charmaine!” (1927)
68. Louis Armstrong “West End Blues” (1928)
69. Billy Murray with Ed Smalle “That Old Gang of Mine” (1923)
70. Fanny Brice “Second Hand Rose” (1922)
71. Charles Harrison “I’ll Be with You in Apple Blossom Time” (1920)
72. Paul Whiteman “Parade of the Wooden Soldiers” (1923)
73. Paul Whiteman “Stumbling” (1922)
74. Rudy Vallee “Honey” (1929)
75. Paul Whiteman “Say It with Music” (1921)
76. Gene Austin “Carolina Moon” (1929)
77. Fred Waring with Tom Waring “Ah! Sweet Mystery of Life” (1928)
78. Gene Austin with Nat Shilkret’s Orchestra “Five Foot Two, Eyes of Blue” (1926)
79. Isham Jones “Swingin’ Down the Lane” (1923)
80. Marion Harris “I’m Just Wild about Harry” (1922)
81. Paul Whiteman with Jack Fulton, Charles Gaylord, & Austin Young “Among My Souvenirs” (1928)
82. Al Jolson “When the Red, Red Robin Comes Bob, Bob, Bobbin’ Along” (1926)
83. Ben Bernie with Arthur Fields “Sleepy Time Gal” (1926)
84. John Steel “The Love Nest” (1920)
85. The Carter Family “Wildwood Flower” (1928)
86. Louise Homer “America the Beautiful” (1925)
87. Maurice Chevalier “Louise” (1929)
88. Benny Krueger “I Cried for You” (1923)
89. Paul Whiteman with the Rhythm Boys “Side by Side” (1927)
90. Paul Whiteman “Linger Awhile” (1924)
91. Paul Whiteman “Hot Lips (He's Got Hot Lips When He Plays Jazz)” (1922)
92. Helen Kane with Leonard Joy’s Orchestra “I Wanna Be Loved by You” (1928)
93. Vincent Lopez “I Want to Be Happy” (1924)
94. Al Jolson “Avalon” (1920)
95. Peerless Quartet “Way Down Yonder in New Orleans” (1922)
96. Ben Pollack with Franklyn Baur “Sweet Sue, Just You” (1928)
97. Paul Whiteman with Jack Fulton “Lover, Come Back to Me” (1929)
98. Paul Whiteman “Oh, Lady Be Good” (1925)
99. Aileen Stanley “Everybody Loves My Baby” (1925)
100. Leo Reisman with Ran Weeks “With a Song in My Heart” (1929)
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First posted 4/4/2012; last updated 10/22/2022. | 
