Based on that songlist, I’d start with “Old Testaments”. It includes all the songs that made him famous.
Once upon a time I had Lasso From El Paso, his first album (I think.) The tribute CD “Pearls in the Snow” is good if you want to hear, say, Willie Nelson singing “Ride 'em Jewboy”. I also have “Under the Double Ego”, which is a mostly good mostly acoustic solo album (mostly notable for “Marylin and Joe”.) I’d start with either “Lasso” or “Old Testaments” though, since they have the hits.
orangecakes: I thought “Dear Abby” was a John Prine tune. Was I wrong or was this a different song?
Since we’re on live stuff, a friend told me about seeing Kinky when somebody thought it would be a good idea to take the kids to the show. He’s doing his usual (blue) banter, and the kids are at the front of the stage with their mouths opening wider and wider, and this in turn is making his guitarist’s face turn redder and redder. Kinky looks over at the guitarist and says “Shoot Frank, I understand. My Momma told me never to say shit or fuck in front of a K-I-D too!” I’ve seen Kinky once. I can’t remember any of what he said, but at one point Sammy Allred, who was playing mandolin, stopped the show to count the audience to see how badly Kinky was screwing him on his pay!