Willie Nelson: What should I buy?

They are two of my favourites as well, and probably as good as any for starting out with. It’s extremely hard to know what to suggest for the OP, as there’s so much good Willie out there, but there’s also a lot of rubbish, as he appears to be quite happy to sing absolutely anything anyone asks him to, and release several albums a year.

Every single album mentioned in the thread so far is great, though, and any one of them would be worth a listen. Don’t accidentally buy his reggae album, whatever you do.

I also love Across the Borderline. I think he’s at his best with plaintive insecure songs; his voice is a bit whiny IMO, and his self-deprecating humor does great service to such songs. The title song from that album.

If you get a chance to see Willie in concert, go. Like you, I’m also mostly a classic rock guy. I thought the Willie concert I went to a couple years ago was fantastic. He covers way more ground than country. Lots of his guitar playing at the concert had a definite blues sound to it.

He also has a powerful stage presence that I can only compare to years ago when I saw Johnny Cash.

This is one of those songs where I can’t believe someone wrote something so great and I love his rendition of it too.

And “Gulf Coast Highway” with him and Emmylou Harris.