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This was a black and white "B" or "C" film of the 40s or 50s.
It was known for introducing a song that became a jazz standard.

A 25 to 30 year old man is singing a song to a 10 to 12 year old girl while riding in a horse carriage that he is holding the reins.
If the horse carriage was a car, he's on the passenger side and she is on the drivers side. I am pretty sure that the male actor and the little girl were not well-known in films.

The camera angle is facing them and no horses can be seen.
He is not dressed as a cowboy, he is dressed in a sports coat and tie of that era.

This is not a live shot, it's obvious that they are in a studio and the background was projected on a film screen.
Prior to that scene, one of those old-style captions pops up on the screen with the text... "Once upon a time, a long time ago in 1946..." or something similar to that.

The girl is initially sad but after the song she becomes happy.
I remember that the male actor didn't do a great job of singing that song.

The male actor's dialogue after the song goes something like this, "You're just jealous... ha ha, oh boy it must be tough to be a girl. How about I take you to [some event] to make you happy". Her response, "You're just saying that because you want to see [some girls name]". His response, "That's not true, why would I have spent that money buying you [something]".

I never saw the movie but I saw this scene on Youtube a while back and I am pulling my hair out trying to find it again.
As you can see, I can remember a lot about the scene but I can't for the life of me remember the song, the actor nor the movie.

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@Walt just for your information, we can further improve suggested edit by clicking "Improve" instead of "Approve" - this save the need to first approve then edit. Thanks for approving! :-) –  Shadow Wizard May 12 at 9:08
    
I know, but unfortunately only thought of the extra edit after clicking 'approve'. ;) –  Walt May 12 at 9:15
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Just to clarify, you refer to "passenger and driver sides", is this US standard, UK standard...? Not all countries are the same. –  JohnP May 12 at 18:20
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BTW, Art, are you logged in on Youtube? Because if you are, Youtube keeps track of every video you've ever watched there under 'watch history' and you'll be able to look for it there. –  Walt May 13 at 10:02
    
en.wikipedia.org/wiki/List_of_1940s_jazz_standards lists 3 song from films. –  Ben Plont Jul 17 at 19:07

3 Answers 3

Could it be On Moonlight Bay? It is a musical from 1951 starring Doris Day. The problem is, the clips I found on YouTube are not black and white, so I'm not sure it is the movie you were talking about. But it may be, because sometimes we stick in our brains wrong memories (unconsciously). This is a link that maybe can be useful to you

.

I simply wrote on Google " "It must be tough being a girl" musical " (writing "to be" instead of "being", as in your question, limited the research to only three results, one of which was this very webpage). Maybe doing the same with the other sentences you quoted could be helpful, but it would be great if you could remember some more characterizing quotations.

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Could it be one of these?

Star Eyes was a song from the film I Dood It.

Laura is a song composed by David Raksin for the film of the same title.

On Green Dolphin Street is a song from a film with the same name.

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This has some of the features of the scene you describe, so I'll offer it as a possibility.

In High Society (1956) C.K. Dexter Haven (Bing Crosby) sings to Caroline Lord (Lydia Reed who was 11 or 12 when filmed). They are not in a carriage, but are sitting on a bench in a garden. He is on their right (passenger side for US automobiles) and she is on their left. He wraps his hands around his knees in a way that could resemble holding reins.

Here is the video on Youtube:

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