Always been a big fan of Dylan's early stuff. Some of the lyrics and emotion on 'Freewheelin' and 'Times A-Changin' is extraordinary. How he manages to achieve this with just guitar and vocals (some harmonica) is brilliant!
In this 'genre', or category of folk music, I've only managed to find odd songs here and there that even come close to this fantastic, raw, outpour of emotion. Anyone got any other recommendations? Here are some examples of other artists I've managed to find.

Sixto Rodriguez - Crucify Your Mind (https://www.youtube.com/watch?v=-qFP-dsl2Z0) If you haven't seen the documentary 'Searching for Sugar Man' I strongly recommend having a look.

Glen Hansard - Leave (https://www.youtube.com/watch?v=TB4RlKFrw3s) Another song with a film behind it funnily enough. ('Once')

Van Morrison - Into The Mystic (https://www.youtube.com/watch?v=CEvsDuJYEnI) Van the Man has a few other good 'uns too I am aware of.

Loudon Wainwright III - Daughter (https://www.youtube.com/watch?v=4dq6G45T97g)

Obviously these are just a few examples, but I suppose they're a point of reference. Basically singer/songwriters with emotion in not only their vocal, but also their lyrics and chord structures.

P.S. I know some on here love Lennon's solo material. I've had a fair crack of it on many occasion, but never really thought much of it I'm afraid. I'm open to suggestions however, in-case I missed an absolute gem somehow.