100 Greatest Songs From 1944

Criteria: These songs from 1944 were chosen and ranked based on their initial & lasting popularity, and on their impact on the overall scope of musical history.

Note: Yearly song lists go by earliest 'release date' (Single, Album, or Country of first release). Not necessarily the year a song peaked in the U.S. charts.

  1. You Always Hurt The One You Love - Mills Brothers
  2. Swinging On A Star - Bing Crosby
  3. Don't Fence Me In - Bing Crosby & Andrews Sisters / Roy Rogers & Sons of Pioneers
  4. Rum And Coca-Cola - Andrews Sisters
  5. G.I. Jive - Louis Jordan
  6. Straighten Up And Fly Right - King Cole Trio
  7. Ac-Cent-Tchu-Ate The Positive - Johnny Mercer & Pied Pipers
  8. I'll Be Seeing You - Bing Crosby / Tommy Dorsey (Frank Sinatra) / Billie Holiday
  9. I'm Making Believe - Ella Fitzgerald & Ink Spots
10. Is You Is Or Is You Ain't My Baby - Louis Jordan / Bing Crosby & Andrews Sisters
11. Into Each Life Some Rain Must Fall - Ella Fitzgerald & Ink Spots
12. Till Then - Mills Brothers
13. I Wonder - Private Cecil Gant
14. A Hot Time in the Town of Berlin - Bing Crosby & Andrews Sisters
15. I'm Beginning To See The Light - Harry James (Kitty Kallen)
16. Have Yourself a Merry Little Christmas - Judy Garland
17. San Fernando Valley - Bing Crosby
18. I Love You - Bing Crosby
19. Gee, Baby, Ain't I Good to You - King Cole Trio
20. Cherry Red Blues - Cootie Williams (Eddie "Cleanhead" Vinson)
21. I'll Walk Alone - Dinah Shore
22. Long Ago (And Far Away) - Helen Forrest & Dick Haymes / Bing Crosby / Jo Stafford
23. Time Waits For No One - Helen Forrest / Johnny Long
24. Cow-Cow Boogie - Ella Fitzgerald & Ink Spots
25. The Trolley Song - Jo Stafford & Pied Pipers / Judy Garland
26. Opus No. 1 - Tommy Dorsey
27. Evil Gal Blues - Dinah Washington
28. It Had to Be You - Helen Forrest & Dick Haymes / Betty Hutton / Artie Shaw
29. (Black Gal) Where Did You Sleep Last Night? - Leadbelly
30. Amor - Bing Crosby / Andy Russel / Xavier Cugat
31. Somebody's Gotta Go - Cootie Williams (Eddie "Cleanhead" Vinson)
32. Smoke on The Water - Red Foley
33. Sweet Lorraine - King Cole
34. Try Me One More Time - Ernest Tubb
35. Too-Ra-Loo-Ra-Loo-Ral (That's An Irish Lullaby) - Bing Crosby
36. Sometimes I'm Happy - Lester Young
37. When My Man Comes Home - Buddy Johnson (Ella Johnson)
38. And Her Tears Flowed Like Wine - Stan Kenton (Anita O'Day)
39. It's Love-Love-Love - Guy Lombardo (Skip Nelson)
40. There Goes That Song Again - Russ Morgan
41. Woodyn' You - Coleman Hawkins
42. My Little Brown Book - Duke Ellington
43. Together - Helen Forrest & Dick Haymes / Guy Lombardo (Tony Craig)
44. Don't Sweetheart Me - Lawrence Welk (Wayne Marsh)
45. Milkman, Keep Those Bottles Quiet - Ella Mae Morse / Woody Herman / King Sisters
46. I'm Wastin' My Tears On You - Tex Ritter
47. I'm Lost - Benny Carter (Dick Gray)
48. Poinciana (Song Of The Tree) - Bing Crosby / David Rose
49. I'll Get By (As Long As I Have You) - Ink Spots
50. Moonlight In Vermont - Billy Butterfield (Margaret Whiting)
51. Artistry In Rhythm - Stan Kenton
52. It Could Happen to You - Jo Stafford / Bing Crosby
53. Main Stem - Duke Ellington
54. Cherry - Erksine Hawkins (Jimmy Mitchelle)
55. Soldier's Last Letter - Ernest Tubb
56. My Mama Don't Allow Me - Arthur "Big Boy" Crudup
57. His Rocking Horse Ran Away - Betty Hutton
58. Dance With A Dolly (With A Hole In Her Stocking) - Russ Morgan / Evelyn Knight
59. Hamp's Boogie Woogie - Lionel Hampton
60. Pretty Kitty Blue Eyes - Merry Macs
61. I Learned a Lesson, I'll Never Forget - Five Red Caps
62. Do Nothin' Till You Hear from Me - Woody Herman
63. Salty Papa Blues - Dinah Washington
64. Tess' Torch Song - Ella Mae Morse / Cootie Williams (Pearl Bailey)
65. White Christmas - Frank Sinatra
66. I Couldn't Sleep A Wink Last Night - Frank Sinatra
67. The Patty Cake Man - Ella Mae Morse
68. How Many Hearts Have You Broken? - Three Suns / Stan Kenton / Tiny Hill
69. Mexico Joe - Ivie Anderson
70. When My Sugar Walks Down the Street - Ella Fitzgerald
71. A Lovely Way To Spend An Evening - Frank Sinatra / Ink Spots
72. You're From Texas - Bob Wills & His Texas Playboys
73. Yesterday's Tears - Ernest Tubb
74. Like Someone in Love - Bing Crosby
75. Saturday Night (Is the Loneliest Night in the Week) - Frank Sinatra
76. I Want Two Wings - Rev. Utah Smith
77. I Stay in the Mood for You - Billy Eckstine
78. There's a New Moon Over My Shoulder- Tex Ritter
79. Good Night, Wherever You Are - Russ Morgan
80. Holiday For Strings - Jimmy Dorsey / Fred Waring's Pennsylvanians
81. The Music Stopped - Woody Herman (Frances Wayne)
82. Just You, Just Me - Lester Young
83. Don't Believe Everything You Dream - Ink Spots
84. Silver Wings In The Moonlight - Freddie Slack (Margaret Whiting)
85. One For My Baby (And One More For The Road) - Lena Horne
86. It's Only A Paper Moon - King Cole Trio
87. By The River Of Roses - Woody Herman
88. Estrellita - Harry James
89. Tico Tico - Ethel Smith / Andrews Sisters
90. Cuban Sugar Mill - Freddie Slack
91. Lili Marline - Perry Como
92. My Funny Valentine - Hal McIntyre (Ruth Gaylor)
93. A Fellow on A Furlough - Phill Hanna / Al Sack
94. An Hour Never Passes - Jimmy Dorsey
95. Once Too Often - Ella Fitzgerald
96. Memphis Blues - Harry James
97. Hurry, Hurry - Benny Carter (Savannah Churchill) / Lucky Millinder (Wynonie Harris)
98. Sam's Got Him - Johnny Mercer
99. D-Day - King Cole Trio
100. There's a Blue Star Shining Bright (In a Window Tonight) - Red Foley
20 more worth mentioning.
101. She Broke My Heart in Three Places - Hoosier Hot Shots
102. I'm Woke Up Now - Big Bill Broozny
103. We Might as Well Forget It - Bob Wills & His Texas Playboys
104. Suddenly It's Spring - Glen Gray (Eugenie Baird) / Harry Sosnik (Hildegarde)
105. Arsenic And Old Lace - Jerry Jerome
106. You Gonna Miss Me When I'm Gone - Tampa Red
107. Back Door Stuff - Jimmie Lunceford
108. Too Late To Worry, Too Blue To Cry - Texas Jim Lewis / Al Dexter & His Troopers
109. Boogie Woogie Ball - Five Red Caps
110. I'm Wasting My Tears On You - Tex Ritter
111. G.I. Blues - Floyd Tillman
112. Here We Go Again - Glenn Miller
113. Someday I'll Meet You Again - Ink Spots / Enric Madriguera
114. I'll Live True to You - Tab Smith (Trevor Bacon)
115. I Wanna Get Married - Gertrude Niesen
116. Robin Hood - Louis Prima
117. These Young Men Blues - Bea Booze
118. Going Out the Back Way - Johnny Hodges
119. Texas Blues - Foy Willing
120. Is It Too Late Now - Jimmie Davis
DigitalDreamDoor Editor Picks for 1944
An unheralded great record from 1944
Adam's choice -
* Date Bait - Roosevelt Sykes
Bruce's choice -
* The Sunny Side Of The Street - Lester Young (Marie Bryant)
Lew's choice -
* Just One More Chance - Cozy Cole's All Stars
Last Updated: 2017-05-03