Listers have put out dark country music, but No. 1 on this list is a deep cut you might have never heard before.

The 1990s just might be the definitive era of sad country music. Legends like Garth Brooks, George Strait and Alan Jackson were at the top of their game during that decade, and young bucks — like an ...

Bob Dylan has covered some of the saddest country songs out there, like “1913 Massacre” by Woodie Guthrie. Dylan can definitely take on a tragic tale or two. So, we think he’d be a perfect match for ...

And you might be surprised to know how Jones came to record what many consider to be the greatest country song of all time, which was a co-write by Bobby Braddock and Curly Putman, who also penned ...