Calexico, "Gypsy's Curse"
The Black Light, the second Calexico album, is really where Calexico became Calexico. The dusty southwestern aesthetic reached full flower, with the rhythms and arrangements being incredibly evocative. I mean, I suppose this track explains it more than I could. They would eventually branch out more and more from this core sound, but never abandon it. But if this is why you love Calexico, this record and The Hot Rail should be at the top of your list.
Lucinda Williams, "Drunken Angel"
I didn't pick up on this record when it was released, despite being reasonably into this sort of music in 1998. I eventually did pick it up mostly by repeatedly seeing it used as a yardstick for other Americana albums. And, yeah, it's as outstanding as its reputation, a record that you can measure other similar albums against.
Farside, "Better Than Crying"
Farside was one of the reasons I stopped using Youtube to host my playlists. I used to upload songs that were missing from Youtube, as unlisted videos, so I could add them to playlists. But Farside's songs kept getting struck as copywrite violations, even though they were unmonetized, and I eventually gave up.
Wait, no, that was Dillinger Four. Whatever. Youtube sucks!
Mayer Hawthorne, "A Long Time"
I sincerely adore songs that are about how much the artist loves their home. There's an authenticity to them that I find really appealing. Nobody shouts out Detroit, or anywhere in Minnesota, or wherever without genuinely loving that place. More of this kind of thing!
Squirrel Bait, "Choose Your Poison"
My goodness, Squirrel Bait were so good.