I don't know about that. There are lots of great singer songwriters out there that write from the heart. In fact they are everywhere, just probably not on top 40 radio. WFUV here in New York is a station pretty much dedicated to this type of music. http://www.wfuv.org/I would not call the context depressed I think it is melancholic. There seems to be no more room in the world today for this kind of stuff.
A great example on their web page is Ani Defranco. I saw her play solo a few years back at Grey fox and she had the entire audience in the palm of her hand.
Sometimes I wish that instead of crying about the fact that people like Hank Williams aren't around, people would start supporting those who are around and are continuing a tradition.
Good example: Always hear that traditional country is dead. But last night in New York, I went to hear fellow forumite Gerald Menke play with the Dixons, and it was a traditional a country set as you could ask for. All original songs as well, except one: There Stands the Glass.
The stuff is out there. Sometimes I think we are all just a little too lazy or complacent to go out and find it.