I have a special place in my heart for To Beat the Devil (esp right now) - a brilliant piece of songwriting that shows mastery of the form in the breaking of its rules, and also Junkie the Juiceman and Me.

I love his voice and generally speaking prefer his versions of his songs to anyone else's (except Janis' Me and Bobby McGee). He doesn't have a perfect voice, but as Emmylou pointed out, your limitations define your style, and there is a special power in hearing the writer of a song sing it the way they hear it in their heads. Help Me Make It Through the Night and Sunday Morning Coming Down.. no one IMO communicated the pain better than Kris did (though Johnny Cash got pretty close on SMCD).