Been looking around on this site and I hear a lot of mentions of different artists and there's that great songwriters thread and all, but I'd like to find out more specifically what are some of the greatest songs, in your opinion? A handful at a time would be nice so we can stay real selective and only hear about your top choices. For me when I think about it a few songs have stood out over the years as strangely ageless, unique, maybe haunting or they have some other quality which just connects. Anyway I plan on listening to as many as possible...
Here's what comes to mind for me without scouring my collection or anything:
Angel Flying Too Close to the Ground - Willie Nelson
Pancho and Lefty - Townes Van Zandt
Levelland - James McMurtry
Not a Drop of Rain - Robert Earl Keen
The Front Porch Song - Robert Earl Keen & Lyle Lovett
My favorite train 'songs' are the classics: Wabash Cannonball and Orange Blossom Special. I don't think that any of these are great. Even Men Who Love Women Who Love Men isn't great in my mind. It just tickles me. He's just more of a tickler than a heart tugger.