So, I’m not looking for a specific song, just a song appropriate for a situation (in the novel I’m working on).
The situation: Teenage boy and blues musician wants to serenade a girl he’s recently met. 1944 New Orleans.
Looking for something he could play and sing outside her window. Bonus points if it’s sweet but a little sad.
Anyone have any thoughts?
You’re in New Orleans…“House of the Rising Sun” has been around in various forms for a long time…at least back to 1905, maybe longer…
Paper moon…1943
No, no, no… here’s your chance to write your own song.
And you won’t have to worry about the music, just write a verse and a chorus, put them in italics, and bingo! If your character’s capable of creativity, you can have it be a song he wrote. Either he’d been working on for years and dedicated it to her, or she gave him the inspiration to compose it,
My four top picks:
Someone to Watch over Me (1926)
**Embraceable You** (1928) **Moonlight Serenade** (1939) **Sentimental Journey** (1944)
Nevermind. My suggestion doesn’t fit the story.
Whatever version you choose, a song about a brothel and gambling joint that ruins people’s lives seems to me like a poor choice for a teenage boy to romantically serenade a girl he’s just met. 
Whatever version you choose, a song about a brothel and gambling joint that ruins people’s lives seems to me like a poor choice for a teenage boy to romantically serenade a girl he’s just met.
Maybe it’s just me, but it seems like a bit of a buzzkill.
If you want to go with the obvious, use “As Time Goes By.”
How about “The Way You Look Tonight”, a big hit for Fred Astaire in 1936. Here’s what an acoustic cover can sound like.
Skylark. Written 1941, one of my faves.
OP specifies a “blues musician.” Songs like Skylark and some others mentioned are not so easy to play.
Jerry Garcia wrote a very beautiful song called “Reuben and Cherise” in 1978, which first appeared on the album Cats Under the Stars. No idea why it’s never became more popular.
It’s not from the 1940s, but it’s about a handsome young New Orleans man who plays on his “painted mandolin” at the Carnival, and his true love and her rival. Chords are available on the internets.
How about Black Betty? (j/k)
Here you can listen to the top popular songs in 1943 and 1944 (and other years):
Consider “Soft Winds,” written in 1940. Easy chords, slow/medium tempo–
You’ll find a number of versions on youtube–I like Dinah Washington’s. You might have to modify the lyrics slightly–change he/him to she/her–
Soft winds whisper
Sweet words to my love
Soft winds, tell him
The dreams I’m dreaming of
He’s gone too long
I’m on the blue sea
Find him, soft winds
And bring him back home to me
He could re-enact Bing Crosby’s seranadefrom Road To Morocco (1942).
This song was first recorded in 1943, and if it’s good enough for Tom to sing outside HIS girl’s window…
“But Not For Me”
Simple chords, published in 1930, about unrequited love.
Ella Fitzgerald (ballad)
Chet Baker (swing)
Dream A Little Dream Of Me, 1931.