Willie Nelson - ...And Then I Wrote (1962)

Willie's very first album! Pretty standard Nashville arrangements of their time, but this album is very nice. At the time Willie was mainly a Nashville songwriter trying to make it as a performer on his own. And while his own versions of "Crazy", etc might not be as good as the hit covers, they still sound pretty impressive here. And even at the start of his career he had a great, unique voice. This is as good of an introduction to classic country for the uninitiated that I can think of.
https://open.spotify.com/album/2Bsr45EWfyrQEUDfGhJwyu