Between 1920 and 1940 there are few available charts (at least that
we can find), hence these results should be treated with caution
since they are based on fairly subjective charts.
| # |
Artist |
Song Title |
Year |
Chart Entries |
| 1 |
Bing Crosby |
Swinging On a Star |
1944 |
US Billboard 1 - May 1944 (28 weeks), US 1940s 1 - Jun 1944, US 1 for 9 weeks Aug 1944, Australia 1 for 1 months Apr 1945, Oscar in 1944, Grammy Hall of Fame in 2002, US BB 3 of 1944, POP 3 of 1944, Europe 14 of the 1940s, AFI 37, RYM 44 of 1944, Brazil 64 of 1945, Acclaimed 1619 |
| 2 |
Bing Crosby & The Andrews Sisters |
Don't Fence Me In |
1944 |
US Billboard 1 - Nov 1944 (21 weeks), US 1940s 1 - Nov 1944, US 1 for 8 weeks Dec 1944, Australia 1 for 3 months Sep 1945, Grammy Hall of Fame in 1998, US BB 4 of 1944, Europe 5 of the 1940s, POP 9 of 1944, Brazil 55 of 1945, Acclaimed 1699 |
| 3 |
Bing Crosby |
I'll be seeing you |
1944 |
US Billboard 1 - Apr 1944 (24 weeks), US 1940s 1 - May 1944, US 1 for 4 weeks Jul 1944, Australia 1 for 1 months Aug 1945, US BB 15 of 1944, Europe 15 of the 1940s, POP 15 of 1944, RYM 43 of 1944, Brazil 83 of 1944 |
| 4 |
Jimmy Dorsey |
Bosame Mucho (Kiss Me Much) |
1944 |
US Billboard 1 - Jan 1944 (23 weeks), US 1940s 1 - Jan 1944, US 1 for 7 weeks Mar 1944, US BB 10 of 1944, Brazil 10 of 1944, POP 10 of 1944, Europe 67 of the 1940s |
| 5 |
Ella Fitzgerald & The Ink Spots |
I'm Making Believe |
1944 |
US Billboard 1 - Nov 1944 (17 weeks), US 1940s 1 - Nov 1944, US 1 for 2 weeks Dec 1944, US BB 14 of 1944, POP 14 of 1944, RYM 23 of 1944, Brazil 32 of 1945 |
| 6 |
Dinah Shore |
I'll Walk Alone |
1944 |
US Billboard 1 - Aug 1944 (25 weeks), US 1940s 1 - Aug 1944, US 1 for 4 weeks Oct 1944, US BB 13 of 1944, POP 13 of 1944, Brazil 57 of 1945, Europe 84 of the 1940s |
| 7 |
Bing Crosby |
I Love You |
1944 |
US Billboard 1 - Apr 1944 (18 weeks), US 1940s 1 - Apr 1944, US 1 for 5 weeks May 1944, US BB 19 of 1944, Europe 21 of the 1940s, POP 23 of 1944, RYM 43 of 1944 |
| 8 |
Bing Crosby |
Too-Ra-Loo-Ra-Loo-Ra |
1944 |
US BB 1 of 1944, Australia 1 for 1 months Dec 1945, POP 1 of 1944, US Billboard 4 - Oct 1944 (12 weeks), US 1940s 4 - Oct 1944, RYM 50 of 1944 |
| 9 |
Guy Lombardo |
It's Love-Love-Love |
1944 |
US Billboard 1 - Mar 1944 (19 weeks), US 1940s 1 - Apr 1944, US 1 for 2 weeks Apr 1944, US BB 20 of 1944, POP 25 of 1944, Brazil 66 of 1944 |
| 10 |
Ella Fitzgerald & The Ink Spots |
Into Each Life Some Rain Must Fall |
1944 |
US Billboard 1 - Nov 1944 (17 weeks), Australia 1 for 1 months Apr 1946, US 1940s 5 - Dec 1944, US BB 18 of 1944, POP 21 of 1944, RYM 24 of 1944, Brazil 56 of 1945 |
| 11 |
The Mills Brothers |
You Always Hurt the One You Love |
1944 |
US Billboard 1 - Jun 1944 (33 weeks), US 1940s 1 - Jul 1944, US 1 for 5 weeks Oct 1944, US BB 6 of 1944, POP 6 of 1944 |
| 12 |
Glen Gray |
My Heart Tells Me (Should I Believe My Heart) |
1944 |
US Billboard 1 - Nov 1943 (21 weeks), US 1940s 1 - Nov 1943, US 1 for 5 weeks Jan 1944, US BB 9 of 1944, POP 19 of 1944 |
| 13 |
Louis Jordan |
GI Jive |
1944 |
US Billboard 1 - May 1944 (25 weeks), RYM 1 of 1944, US 1940s 3 - Jun 1944, US BB 16 of 1944, POP 18 of 1944, Brazil 74 of 1945 |
| 14 |
Harry James & Dick Haymes |
I'll Get By (As Long As I Have You) |
1944 |
US Billboard 1 - Apr 1944 (28 weeks), US 1940s 1 - Apr 1944, US 1 for 4 weeks Jun 1944, Europe 41 of the 1940s |
| 15 |
Judy Garland |
The Trolley Song |
1944 |
US BB 2 of 1944, POP 2 of 1944, US Billboard 4 - Nov 1944 (8 weeks), US 1940s 4 - Dec 1944, RYM 12 of 1944, AFI 26 |
| 16 |
Stan Kenton |
Artistry in Rhythm |
1944 |
Grammy Hall of Fame in 1985, US BB 9 of 1943, POP 9 of 1943, US Billboard 16 - Nov 1944 (1 weeks), RYM 23 of 1945, Acclaimed 1921 |
| 17 |
Bing Crosby |
San Fernando Valley |
1944 |
US Billboard 1 - Mar 1944 (22 weeks), US 1940s 2 - Apr 1944, US BB 11 of 1944, POP 11 of 1944, RYM 49 of 1944 |
| 18 |
The Andrews Sisters |
Shoo-Shoo Baby |
1944 |
US Billboard 1 - Jan 1944 (21 weeks), US 1940s 2 - Jan 1944, US BB 12 of 1944, POP 12 of 1944, Brazil 67 of 1944 |
| 19 |
Nat King Cole |
Straighten Up & Fly Right |
1944 |
Grammy Hall of Fame in 1998, RYM 5 of 1944, US Billboard 9 - Jun 1944 (7 weeks), US 1940s 9 - Jun 1944, POP 16 of 1944 |
| 20 |
Merry Macs |
Mairzy Doates |
1944 |
US Billboard 1 - Feb 1944 (15 weeks), US 1940s 2 - Feb 1944, US BB 5 of 1944, POP 5 of 1944 |
| 21 |
Louis Jordan |
Is You Is or Is You Ain't (Ma' Baby) |
1944 |
RYM 1 of 1944, US Billboard 2 - Jul 1944 (19 weeks), US 1940s 5 - Sep 1944 |
| 22 |
Frank Sinatra |
A Lovely Way To Spend An Evening |
1944 |
Australia 1 for 1 months Dec 1944, US Billboard 11 - Mar 1944 (4 weeks), RYM 21 of 1944, Europe 28 of the 1940s |
| 23 |
Frank Sinatra |
White Christmas |
1944 |
US Billboard 5 - Dec 1945 (4 weeks), US 1940s 7 - Dec 1944, Europe 18 of the 1940s, Scrobulate 42 of christmas, RYM 105 of 1946 |
| 24 |
Bing Crosby |
Long Ago & Far Away |
1944 |
Australia 1 for 1 months May 1945, US Billboard 5 - Jul 1944 (9 weeks), US 1940s 5 - Jul 1944 |
| 25 |
Bing Crosby & The Andrews Sisters |
Vic'try Polka |
1944 |
Australia 1 for 1 months Sep 1944, US Billboard 5 - Jan 1944 (13 weeks), RYM 6 of 1943 |
| 26 |
Frank Sinatra |
I Couldn't Sleep A Wink Last Night |
1944 |
US Billboard 4 - Aug 1944 (14 weeks), US 1940s 5 - Feb 1944, RYM 21 of 1944, Europe 27 of the 1940s |
| 27 |
Helen Forrest & Dick Haymes |
Long Ago & Far Away |
1944 |
US Billboard 2 - Apr 1944 (18 weeks), US 1940s 2 - May 1944, Brazil 53 of 1945 |
| 28 |
Jo Stafford |
It Could Happen to You |
1944 |
US BB 8 of 1944, POP 8 of 1944, US Billboard 10 - Sep 1944 (10 weeks), US 1940s 10 - Sep 1944 |
| 29 |
The Ink Spots |
A Lovely Way To Spend An Evening |
1944 |
Australia 1 for 1 months Dec 1944, US Billboard 16 - Mar 1944 (1 weeks) |
| 30 |
Bing Crosby |
It Could Happen to You |
1944 |
Australia 1 for 2 months Jun 1945, US Billboard 18 - Dec 1944 (2 weeks) |
| 31 |
Bing Crosby |
Poinciana (Song Of The Tree) |
1944 |
US Billboard 3 - Feb 1944 (15 weeks), US 1940s 5 - Mar 1944, RYM 49 of 1944 |
| 32 |
Stan Kenton |
And Her Tears Flowed Like Wine |
1944 |
US Billboard 4 - Sep 1944 (18 weeks), US 1940s 4 - Oct 1944, Brazil 84 of 1945 |
| 33 |
Duke Ellington |
Black, Brown & Beige |
1944 |
Grammy Hall of Fame in 1990, Acclaimed 1269 |
| 34 |
Helen Forrest |
Time Waits For No One |
1944 |
US Billboard 2 - Aug 1944 (18 weeks), US 1940s 2 - Aug 1944 |
| 35 |
David Rose |
Holiday for strings |
1944 |
US Billboard 2 - Feb 1944 (21 weeks), US 1940s 2 - Feb 1944 |
| 36 |
Bing Crosby & The Andrews Sisters |
Is You Is or Is You Ain't (Ma' Baby) |
1944 |
US Billboard 2 - Sep 1944 (12 weeks), US 1940s 2 - Sep 1944 |
| 37 |
The Mills Brothers |
Till Then |
1944 |
Peel list 4 of 1944, US Billboard 8 - Aug 1944 (16 weeks), US 1940s 8 - Sep 1944 |
| 38 |
The Pied Pipers & Jo Stafford |
The Trolley Song |
1944 |
US Billboard 2 - Oct 1944 (14 weeks), US 1940s 2 - Oct 1944 |
| 39 |
Lionel Hampton |
Hamp's Boogie Woogie |
1944 |
POP 4 of 1944, RYM 13 of 1944, US Billboard 23 - Sep 1944 (1 weeks) |
| 40 |
Harry James |
Cherry |
1944 |
US Billboard 4 - Jan 1944 (10 weeks), US 1940s 10 - Jan 1944, Brazil 100 of 1945 |
| 41 |
Les Brown |
Twilight Time |
1944 |
US BB 7 of 1944, POP 7 of 1944, US Billboard 16 - Mar 1945 (1 weeks) |
| 42 |
Mary Martin |
I'll Walk Alone |
1944 |
US Billboard 6 - Oct 1944 (13 weeks), US 1940s 6 - Oct 1944, Brazil 97 of 1945 |
| 43 |
Woody Herman |
Do Nothin' Till You Hear From Me |
1944 |
US Billboard 7 - Feb 1944 (11 weeks), US 1940s 9 - Mar 1944, RYM 27 of 1943 |
| 44 |
Perry Como |
Long Ago & Far Away |
1944 |
US Billboard 8 - May 1944 (7 weeks), US 1940s 8 - May 1944, Europe 31 of the 1940s |
| 45 |
Bing Crosby |
Amor |
1944 |
US Billboard 2 - Jul 1944 (16 weeks), US 1940s 4 - Jul 1944 |
| 46 |
Duke Ellington |
Do Nothin' Till You Hear From Me |
1944 |
US Billboard 10 - Feb 1944 (6 weeks), US 1940s 10 - Feb 1944, POP 20 of 1944 |
| 47 |
Ella Fitzgerald & The Ink Spots |
Cow Cow Boogie |
1944 |
US Billboard 10 - Mar 1944 (8 weeks), RYM 11 of 1944, POP 24 of 1944 |
| 48 |
Duke Ellington |
Main Stem |
1944 |
RYM 8 of 1943, POP 17 of 1944, US Billboard 23 - Mar 1944 (1 weeks) |
| 49 |
Judy Garland |
Have Yourself a Merry Little Christmas |
1944 |
RYM 8 of 1944, US Billboard 27 - Dec 1944 (1 weeks), AFI 76 |
| 50 |
Russ Morgan |
Dance With A Dolly (With a Hole In Her Stocking) |
1944 |
US Billboard 3 - Nov 1944 (12 weeks), US 1940s 3 - Nov 1944 |