Matt M
Santa Extraordinaire
Agreed with @MikeH that the live album is a great place to start - he is a storyteller at heart - along with the debut. I was lucky enough to see him on The Missing Years tour in '92 and have been hooked ever since. Bruised Orange is pretty great, but I'd be sure to work Sweet Revenge into your first five. It's a perfect blend of his sense of humor and storytelling prowess. Not to mention, that album cover.
My prediction: you'll have more Prine records than me by this time next month.
I don't know about that. We'll see soon enough I guess!