‘You’ll Never Know’ would be a good choice I think. Recent to 1944, and just right for singing to someone you don’t really know very well.
Helen O’Connell - All Of Me w/The Jimmy Dorsey Orchestra (1939)
I agree. Also for a more practical reason, if you intend to publish this novel and are not just writing it for yourself to read, if you use a real song, you’re going to have to deal with clearances for the song. (Music copyrights are nasty.) If a little-known author submits something like that to a publisher, that might be a turnoff right there. If you’re lucky, the publisher might make you replace it, if not, they might just stop reading.
It’s a novel, not a movie or a play script. It doesn’t need any more than just naming the song. No need to include any of the lyrics. No copyright issues just naming a song.
Lovely. Lots of very famous people have done this song, but I’m partial to this version.
Maybe listen to some actual guitar-accompanied (I assume what your protagonist is playing is a guitar?) vocal recordings from the era and find out the sort of thing singers would actually sing solo to their own guitar accompaniment?
I think many of the classic soloist-and-orchestra ballads like “You’ll Never Know” or “All of Me” might be perceived in that era as sounding kind of silly with nothing but guitar accompaniment, if guitar arrangements for them even existed at the time.
It’s an interesting question. Music history is not a strong suite for me, but your request sent me browsing through YouTube and Wikipedia.
There were melancholy blues songs from before/during WWII, but not many that were sweet and melancholy. (A famous melancholy blues song: Robert Johnson’s Love In Vain)
I did a lot of self-censoring – rejecting songs because they were about about missing former lovers, or because they were too romantically explicit, or because the music or lyrics were too far removed from the blues.
My top candidate is The Very Thought of You. That’s Billie Holiday’s version. The song was originally released in England, but reached #1 in America in the mid-1930s. Which can be a good thing, because if a person is serenading someone, a well-known song doesn’t have to exactly match the circumstances of their relationship – the performance and mood are more important than the lyrical details.
Louisiana Fairy Tale seems to fit the bill, but it was written in 1935. You may know it as the original theme to This Old House. It’s a very romantic song that a young man might sing to a young woman.
Taking a Chance on Love was written in 1943 for the musical Cabin in the Sky. It’s romantic, but maybe not the sort of thing a teenaged boy would sing (the lyrics imply the singer had previous relationships that went sour).