I live with my partner these days, so I'm often watching shows I wouldn't normally watch, and the majority are pretty good. Relevant to these forums, the Marvelous Mrs. Maisel has some pretty great music from the time (late 50's, early 60's - but like, the Kennedy/Mad Men 60's, not the hippie 60's). Here's a few tracks I found through watching:
How Are Ya Fixed For Love - Keely Smith & Frank Sinatra
Is you is, or is you ain't - Louis Jordan
WPA - Ethan Lipton & His Orchestra