1. “White Christmas” Bing Crosby with the Ken Darby Singers (1942) 
2. “Stardust” Artie Shaw (1941) 
3. “Rudolph, the Red-Nosed Reindeer” Gene Autry (1949) 
4. “Sentimental Journey” Les Brown with Doris Day (1945) 
5. “Paper Doll” The Mills Brothers (1943) 
6. “As Time Goes By” Dooley Wilson (1942) 
7. “Near You” Francis Craig with Bob Lamm (1947) 
8. “I’ll Never Smile Again” Tommy Dorsey with Frank Sinatra & The Pied Pipers (1940) 
9. “Chattanooga Choo Choo” Glenn Miller with Tex Beneke & the Four Modernaires (1941) 
10. “The Christmas Song” Nat “King” Cole (1946) 

11. “Riders in the Sky (A Cowboy Legend)” Vaughn Monroe (1949) 
12. “Swinging on a Star” Bing Crosby with John Scott Trotter’s Orchestra & the Williams Brothers Quartet (1944) 
13. “Body and Soul” Coleman Hawkins (1940) 
14. “Buttons and Bows” Dinah Shore and Her Harper Valley Boys (1948) 
15. “When You Wish Upon a Star” Cliff Edwards (1940) 
16. “Peg O’ My Heart” The Harmonicats (1947) 
17. “I’ll Be Seeing You” Bing Crosby with John Scott Trotter’s Orchestra (1944) 
18. “Frenesi” Artie Shaw (1940) 
19. “The Gypsy” The Ink Spots (1946) 
20. “I’ve Heard That Song Before” Harry James with Helen Forrest (1943) 

21. “Blues in the Night (My Mama Done Tol’ Me)” Woody Herman (1941) 
22. “Some Enchanted Evening” Perry Como (1949) 
23. “For Me and My Gal” Judy Garland & Gene Kelly (1942) 
24. “Don’t Fence Me In” Bing Crosby with the Andrews Sisters (1944) 
25. “Take the ‘A’ Train” Duke Ellington (1941) 
26. “Twelfth Street Rag” Pee Wee Hunt (1948) 
27. “Nature Boy” Nat “King” Cole with Frank DeVol (1948) 
28. “Till the End of Time” Perry Como (1945) 
29. “This Land Is Your Land” Woody Guthrie (1944) 
30. “You’ll Never Know” Dick Haymes with the Song Spinners (1943) 

31. “That Old Black Magic” Glenn Miller with Skip Nelson (1943) 
32. “Rum and Coca-Cola” The Andrews Sisters (1945) 
33. “Amapola (Pretty Little Poppy)” Jimmy Dorsey with Bob Eberly & Helen O’Connell (1941) 
34. “Ac-Cent-Tchu-ate the Positive” Johnny Mercer with the Pied Pipers (1945) 
35. “Heartaches” Ted Weems with Elmo Tanner (1947) 
36. “Pistol Packin’ Mama” Al Dexter (1943) 
37. “Let It Snow! Let It Snow! Let It Snow!” Vaughn Monroe (1945) 
38. “Besame Mucho (Kiss Me Much)” Jimmy Dorsey with Bob Eberly & Kitty Kallen (1944) 
39. “Ballerina” Vaughn Monroe (1947) 
40. “I’m Looking Over a Four-Leaf Clover” Art Mooney (1948) 

41. “Sunday, Monday or Always” Bing Crosby with the Ken Darby Singers (1943) 
42. “I’ll Get By As Long As I Have You” Harry James with Dick Haymes (1944) 
43. “Cruising Down the River” Blue Barron & His Orchestra (1949) 
44. “On the Atchison, Topeka and Santa Fe” Johnny Mercer with the Pied Pipers (1945) 
45. “I’m So Lonesome I Could Cry” Hank Williams (1949) 
46. “Jingle, Jangle, Jingle” Kay Kyser with Harry Babbitt & Julie Conway (1942) 
47. “Moonlight Cocktail” Glenn Miller with Ray Eberle & The Modernaires (1942) 
48. “I’ve Got a Gal in Kalamazoo” Glenn Miller with Tex Beneke & Marion Hutton (1942) 
49. “People Will Say We’re In Love” Bing Crosby with Trudy Erwin (1943) 
50. “Oh What It Seemed to Be” Frankie Carle with Marjorie Hughes (1946) 

51. “There! I’ve Said It Again” Vaughn Monroe (1945) 
52. “That Lucky Old Sun” Frankie Laine with Judd Conlon’s Rhythmaires, Harry Geller’s Orchestra, & Carl Fischer Orchestra (1949) 
53. “I Love You for Sentimental Reasons” The Nat “King” Cole Trio (1946) 
54. “Tangerine” Jimmy Dorsey’s Orchestra with Bob Eberly & Helen O’Connell (1942) 
55. “Daddy” Sammy Kaye (1941) 
56. “Boogie Woogie Bugle Boy” The Andrews Sisters (1941) 
57. “God Bless the Child” Billie Holiday (1941) 
58. “Tuxedo Junction” Glenn Miller (1940) 
59. “The Trolley Song” Judy Garland (1944) 
60. “Fools Rush in Where Angels Fear to Tread” Glenn Miller (1940) 

61. “The Woodpecker Song” Glenn Miller with Marion Hutton (1940) 
62. “It Might As Well Be Spring” Dick Haymes (1945) 
63. “There Are Such Things” Tommy Dorsey with Frank Sinatra & The Pied Pipers (1942) 
64. “Don’t Sit Under the Apple Tree with Anyone Else But Me” Glenn Miller with Tex Beneke & the Modernaires (1942) 
65. “Manana Is Soon Enough for Me” Peggy Lee (1948) 
66. “To Each His Own” Eddy Howard (1946) 
67. “Smoke! Smoke! Smoke! That Cigarette” Tex Williams (1947) 
68. “Taking a Chance on Love” Benny Goodman with Helen Forrest (1940) 
69. “Now Is the Hour (Māori Farewell Song)” Bing Crosby with the Ken Darby Singers (1948) 
70. “Long Ago and Far Away” Helen Forrest with Dick Haymes (1944) 

71. “You’re Breaking My Heart” Vic Damone (1949) 
72. “Shoo-Shoo Baby” The Andrews Sisters (1943) 
73. “I’ll Be Home for Christmas” Bing Crosby with John Scott Trotter’s Orchestra (1943) 
74. “Green Eyes (Aquellos Ojos Verdes)” Jimmy Dorsey with Bob Eberly & Helen O’Connell (1941) 
75. “There’ll Be Some Changes Made” Benny Goodman with Louise Tobim (1941) 
76. “Move on Up a Little Higher” Mahalia Jackson (1948) 
77. “You Always Hurt the One You Love” The Mills Brothers (1944) 
78. “Santa Claus Is Coming to Town” Bing Crosby with the Andrews Sisters (1947) 
79. “Don’t Get Around Much Anymore” The Ink Spots (1943) 
80. “If I Loved You” Perry Como (1945) 

81. “Boogie Chillen” John Lee Hooker (1949) 
82. “A Tree in the Meadow” Margaret Whiting (1948) 
83. “Dream (When You’re Feeling Blue)” The Pied Pipers with Paul Weston (1945) 
84. “My Funny Valentine” Hal McIntyre with Ruth Gaylor (1945) 
85. “I Can Dream, Can’t I?” The Andrews Sisters (1949) 
86. “Mule Train” Frankie Laine & the Muleskinners (1949) 
87. “A Little Bird Told Me” Evelyn Knight & Stardusters (1948) 
88. “I Had the Craziest Dream” Harry James with Helen Forrest (1943) 
89. “Laura” Woody Herman (1945) 
90. “I’ll Walk Alone” Dinah Shore (1944) 

91. “You Are My Sunshine” Jimmie Davis (1940) 
92. “Imagination” Glenn Miller (1940) 
93. “Maria Elena” Jimmy Dorsey with Bob Eberly (1941) 
94. “Praise the Lord and Pass the Ammunition ” Kay Kyser with Glee Club (1942) 
95. “Five Minutes More” Frank Sinatra (1946) 
96. “Oh What a Beautiful Mornin’” Bing Crosby with Trudy Erwin & the Sportsment Glee Club (1943) 
97. “It’s Been a Long, Long Time” Bing Crosby with the Les Brown Trio (1945) 
98. “On a Slow Boat to China” Kay Kyser with Harry Babbitt & Gloria Wood (1948) 
99. “Baby, It’s Cold Outside” Johnny Mercer with Margaret Whiting (1949) 
100. “A String of Pearls” Glenn Miller (1942)