Jimmy Buffett

Sturgill on Fallon
He is country, but he is more than that. Sturgill Simpson's music has the unique ability to appeal to all music lovers. Play one of his songs for that friend of yours that "absolutely hates" country. They'll like it.
Jesse Winchester is not a huge household name in these whereabouts, although he should be, because he did not seek commercial success:
"I'd rather just hang in there all the time with good music, slow and steady, and share it, rather than set the world on fire all at once...