1. Swinging On A Star – Bing Crosby
2. Trolley Song – Judy Garland
3. Besame Mucho – Jimmy Dorsey
4. You Always Hurt The One You Love – Mills Brothers
5. Mairzy Doates – Merry Macs
6. I’ll Be Seeing You – Bing Crosby
7. Twilight Time – Les Brown
8. It’s Love-Love-Love – Guy Lombardo
9. My Heart Tells Me – Glen Gray
10. I Love You – Bing Crosby
11. I’ll Walk Alone – Dinah Shore
12. I’m Making Believe – Ella Fitzgerald & Ink Spots
13. Straighten Up And Fly Right – The King Cole Trio
14. Til Then – The Ames Brothers
15. I’ll Get By – Harry James
16. Long Ago – Dick Haymes and Helen Forrest
17. Amor – Andy Russell
18. G.I. Jive – Louis Jordan and his Tympany Five
19. Long Ago – Bing Crosby
20. Saturday Night Is the Loneliest Night of the Week – Frank Sinatra
21. Into Each Life Some Rain Must Fall – Ella Fitzgerald & Ink Spots
22. I’m Lost – Benny Carter
23. Main Stem – Duke Ellington
24. Cow-Cow Boogie -(Cuma-Ti-Yi-Yi-Ay) – Ink Spots with Ella Fitzgerald
25. Amor – Bing Crosby
26. Long Ago – Jo Stafford
27. And Her Tears Flowed Like Wine – Stan Kenton
28. Cherry – Harry James
29. Shoo-Shoo Baby – Andrews Sisters
30. Hamp’s Boogie Woogie – Lionel Hampton
31. San Fernando Valley – Bing Crosby
32. Don’t Sweetheart Me – Lawrence Welk
33. A Hot Time In the Town of Berlin – Bing Crosby & the Andrews Sisters
34. It Had To Be You – Dick Haymes and Helen Forrest
35. Time Waits For No One – Helen Forrest
36. Shoo-Shoo Baby – The Andrews Sisters
37. Do Nothin’ Till You Hear From Me – Duke Ellington
38. I Couldn’t Sleep A Wink Last Night – Frank Sinatra
39. Is You Is or Is You Ain’t – The Andrews Sisters
40. It Could Happen to You – Jo Stafford

You may notice that the list above doesn’t quite agree with “Top 40” or other lists you’ve seen; that’s because it takes more facts into consideration, along with a few intangibles. For example, Judy Garland’s The Trolley Song scores higher on this list than Jimmy Dorsey’s Besame Mucho, even though Garland’s song never reached number one — and Dorsey had the top spot for seven straight weeks. It was obviously a bigger song at the time, yet The Trolley Song is a standard known to young and old alike more than 60 years later. As trends change, as old standards are slotted into new movie soundtracks, this list can and will change with those trends. Each of these annual charts are re-evaluated every 6-8 months. For example, a resurgence in Louis Jordan sales — and the fact that he’s finally getting credit for his contribution to the future of pop music — sees his songs steadily move up the charts of the 1940s with the passage of time.

In 1944, as in previous years, Bing Crosby ruled the charts. Seven songs make this list, and we could lobby for one or two others. Ask most people who was the biggest singing star of the 1940s, and the universal answer is Frank Sinatra. Ol’ Blue Eyes had his hits, to be sure, and his mere presence created near-riot situations around the country. But it was Der Bingle who ruled the charts. Sinatra was the “Elvis” of his day, except he didn’t garner nearly as many number one records as Presley would a dozen years later.

Two unlikely groups also defined the decade. First one that comes to mind is The Andrews Sisters. Their vocal style and all-American spirit worked perfectly during the war years. They were just as comfortable fronting Glenn Miller as Desi Arnaz, working a song with Abbott & Costello or Guy Lombardo. They worked with bandleader Bob Crosby and then went on to record 47 songs with his brother, the aforementioned Bing. Of those 47 songs, 23 made it to the charts. A lot of sister vocal teams have followed, but none have come close to Maxene, Patty, and LaVerne.

The other vocal group to dominate the decade was The Mills Brothers. Although not nearly as ubiquitous as the Andrews Sisters, their run was impressive mainly because they were a “comeback” group. In the early 1930s John Mills Jr., Herbert Mills, Harry Mills, and Donald Mills had a string of hits working America’s most popular radio show with Rudy Vallee. They had numerous film appearances, and amazed listeners with their talent for making “four boys and a guitar” sound as if an entire band were playing. By 1934, The Mills Brothers became the first African-Americans to give a command performance before British royalty. In 1939 they returned to Europe, and toured South America as well. Due to the difficulties of war time travel, the group didn’t return to the USA until late 1941, and found that their place had been usurped by The Ink Spots. The Mills boys roared back with a vengeance in 1943 with Paper Doll, which spilled over into the first four weeks of January 1944 at the #1 spot on the charts. The Ink Spots were a great vocal group, but their recordings aren’t nearly as listenable today as The Mills Brothers.

It’s interesting how certain songs are charted by one artist, then become synonymous with another act. Such is the case with Crosby’s I’ll Be Seeing You, which hit #1 in July 1944. It did a brief shuffle at the top with Harry James’ I’ll Get By, then stayed at the top until Bing knocked himself out with Swinging On a Star. Bing’s run at the top actually began on May 6th, and held the top spot with three songs until the first week of October, with the exception of four weeks that James was #1. Anyway, the point is that I’ll Be Seeing You was a huge sentimental hit in a country slugging it out in Europe and the Pacific. But for all of Bing’s success in 1944, the song became better known for being associated with Liberace, who embraced it as a sort of theme song. Today even those old enough to remember Bing’s version need to be reminded that it was Crosby — not Liberace — who made the song a hit.