There are some problems for the 1944 chart details in that very few are available. However, we do have the top five very clearly recorded. These are:
At number 5 we have Ella Fitzgerald and The Ink Spots with ‘I’m Making Believe’ that entered the charts in November 1944 and for 2 weeks in December were at number 1.
Number 4 had Bing Crosby telling someone that ‘I Love You’. It came into the charts in April 1944 and was 5 weeks at number 1 in May’.
Number 3 was also Bing – this time saying ‘I’ll be Seeing You’. This hit the lists in May 1944 and was number 1 for 4 weeks in July
Number 2 has a slight change in that Bing here was accompanied with the Andrew Sisters who was asking Bing to ‘Don’t Fence Me In’. This hit the charts in November and was number 1 for 8 weeks.
Number 1 had – surprise surperise – was Mr Bing Crosby ‘Swinging on a Star’. That came to the charts in June 1944 and for 9 weeks in August 1944 and beyond was top of the list.
There was a link here. ‘Going My Way’ was a 1944 movie that starred Bing Crosby and Barry Fitzgerald and revolved around a young Priest played by Bing who comes, secretly, to the aid of an older priest who is about to lose his parish. The older Priest – Father Fitzgibbon – was played by Barry Fitzgerald and both asked “Would You Like To Swing On A Star?”. That and “Too – Ra – Loo – Ra – Loo – Ra”, were both part of this motion picture that was not a musical as much as a film that involved music.
The story of “Would You Like To Swing On A Star?” became the key to getting money to save the parish and the song has an interesting history. Jimmy Van Heusen, a song writer who was working on the film was at Crosby’s house for dinner one evening. One of the Crosby’s sons complained of not wanting to go to the school the next day. Crosby looked at his son and said to him, “If you don’t go to school, you might grow up to be a mule. Do you wanna do that?” The rebuke became the inspiration that would inspire an Academy Award Winning song!