My first recommendation is Canadian folk singer Stan Rogers. Below are some of his songs that I think fit what you are looking for, but if you like these I highly recommend checking out his entire catalogue:

Barrett's Privateers: https://www.youtube.com/watch?v=3T0Ruhb734U

Harris and the Mare: https://www.youtube.com/watch?v=Sw2Me2pPQuY

Cliffs of Baccalieu: https://www.youtube.com/watch?v=FQ8wo2MFtS8

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My second recommendation is the soundtrack to the movie O Brother, Where Art Thou - it is 100% great, old-timey music.