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
    1943   |   1945

Last Updated: 2017-05-03