The Saddest Band I've Ever Heard
 

Souled American.

Not on Spotify, hard to find their music but if you like some rough around the edges Alt-country with a sad lean then you need to hear the albums "Fe" and "Around the Horn" at the very least. The plucked bass is definitely a stand out.

Song Highlights:

Make me laugh, Make me cry
Around the horn
You
Feel Better
The Torch Singer - they do a slow drawn out John Prine cover

I can't post links yet as I am too new a user but you can listen to Around the Horn album on Youtube.

Sorry if you have to do some digging to find it but it's well worth it if this is your style!

Yeah you can post links, but have these on me:

The National is the saddest band I know