I’m not really a country music fan, but I’ll listen to John Hiatt just about any time. His album Slow Turning is terrific.
RR
First, you’re probably mostly looking for the genre known as ‘alt country’ (put a newsgroup style dot in between the words if you want to be 90’s hip). Even if the old stuff, though, remember, country music is like cholesterol: there is a good kind.
Second, Willie Nelson (it took 48 posts to mention him?!!). While he does plenty of ‘three chords and the truth’ songs, he’s also capable of jazz-like complexity (“Crazy”, or jazzy covers of Cole Porter, etc.). Check out Stardust or Songs (I mean, you can’t get much more intelligent than doing a Kermit the Frog cover, can you?).
Echo John Prine, if you put him in Country rather than Folk.
(And astorian’s right. How many intelligent Top 40 Rock songs are there, after all?)
You might want to check out Grant Lee Buffalo and the further works of its lead singer Grant Lee Phillips. Described by Wikipedia as Americana, it is brilliant music and might be right up your alley.
I’ll have to third the Old 97s. I think 'Too Far to Care’might be the best place to start, every track on there is a keeper. Even as a total hiphop head, this album is still probabably in my top 10 all time. Keep an ear out too for the songs by their bassist, Murray Hammond; there are at least one or two an album and those are always great.
I’d agree with John Prine, though he was considered folk when he first started.
Another group that really bridged the gap between country and rock (back when there was an actual gap) was Poco. Remember, when the Eagles came along, they were considered Poco imitators. Poco made some amazing music.
I’m bookmarking this thread. Among the many artists listed that I’ve listened to and loved, there isn’t really one I’d argued against, and of the ones I’m not familiar with, I’m eager to give a try.
I really do love country music, but what I hear on the radio is crap–pap, as it’s been put. The real good stuff is not on the radio, alas.
I thought of another suggestion: k d lang’s Shadowland–her take on country standards and should-be standards.
And someone who really, really should have been far more rich and famous and celebrated: Gail Davies. I love her. The fact that she never became a huge star is a grave injustice.
I’ll add to the Lyle Lovett - Robert Earl Keen Jr. pile on.
Also, James McMurtry (son of Larry McMurtry, for what it’s worth) writes fairly intelligent if painfully cynical songs. The subjects of his songs tend to be updated versions of the people that his dad wrote about when he was young - people, often in rural Texas and Oklahoma, who are running out of dreams and are starting to run on fumes.
Bill Malonee and the Vigilantes of Love
The Handsome Family
Allison Moorer
I’ll 2nd this.
Also at the Dame, but in 2003.
I thought of another one for this thread — Robbie Fulks, though he may be a little hard to find. He appeared with Junior on Austin City Limits several years ago. I have his album Country Love Songs.
Surprised that this is the only mention of Marty in this thread.(that I saw)
Steve Earle gets another vote
I resent the implication that you can’t write an intelligent song about getting drunk, or your wife leaving, or getting drunk because your wife’s leaving, or your wife leaving because you’re a drunk. (See, the entire George Jones catalogue, and most of Hank Williams’s.)
oops
Great! This thread is still active…
Another great Waylong Jennings album is Honky Tonk Heroes. With songs by Bill Joe Shaver, this is the true Outlaw collection. Before Nashville PR started using the term.
I wanted to recommend Merle’s tribute to Bob Wills, but it’s OOP & expensive. But Merle shows up for a couple of tunes on The Last Time. Along with a bunch of Playboy vets. “Intelligent” lyrics are great–but sometimes you want to swing.
Marty’s “El Paso City” is another one–put out twenty years after “El Paso”–listen to them in chronological order.
Another Steve Earle fan, as well as Townes Van Zandt. A fantastic new singer/songwriter is Justin Townes Earle, son of Steve and named for Townes. His new album, “The Good Life”, is fantastic.
Robbie Fulks was mentioned above. I’ve got all his records. If you want intelligent country music, look no further. The man is a genius.
And he wrote the definitive song about *dumb *country music. Check out “Fuck this Town.”
I hate to “post and run” but I’ve been very busy lately. I’ll try to listen to some of these songs and get back to y’all when I can. 
Disclaimer - I don’t like Country &/or Western music but I once had a boyfriend who loved it… Interestingly he is Black too… Kind of kills that argument in the other thread re: hip hop and rap, but I digress… When I was with him, riding along in the truck, listening to KIKK (any accident in those call letters - this IS TX) a song comes on, whiney ballad about the “Beaches of Cheyenne”. OK, I’m ASSuming he’s singing about Cheyenne Wyoming… It IS country and WESTERN music, right?
Beaches? In Cheyenne, WY??? I rest my case.
Here are the lyrics - Garth Brooks - The Beaches Of Cheyenne lyrics | LyricsFreak lest you think I’m making it up… I am new and not to be fully trusted yet!
Apparently, according to a tourist website for Cheyenne, beaches. I kind of think a “beach” must butt up against an ocean or a gulf… Lemme get a map. Nope, landlocked!