Otis Lee Crenshaw*.
An ex-con from Tennessee, he’s one of the funniest and cleverest lyricists I’ve ever heard. I went to see him live and nearly died because I couldn’t breathe because I was laughing so hard.
Highlights include Women Call It Stalking (I Just Call It Selective Walking) and Show Me On The Doll Where He Touched You.
*Actually Rich Hall in a Confederate bandana.
Although commonly listed as folk/rock I think the boys from the Catskill Mountains, The Felice Brothers are really alt country. At this page you can listen to
Frankie’s Gun
*My car goes
Chicago
Every weekend to pick up some cargo
I think I know the bloody way by now, Frankie
And turn the god damn radio down, thank you
Pull over
Count the money
But don’t count the thirty in the glove box buddy
That’s for to buy Lucille some clothes
Bang bang bang went Frankie’s gun
He shot me down Lucille
He shot me down *
and
Whiskey In My Whiskey
*I put some whiskey into my whiskey
I put some heartbreak into my heart
I put my boots on that ole dance floor
I put three rounds Lord, in my 44
I love the girl, she was my sunshine
Her name was Eleanor Caroline
She got fast, with a friend of mine
At the dance hall Lord, on the county line
*
You can find lots of clips including live stuff on youtube. Superb musicianship and just a fantastic sound. I’m surprised that they aren’t huge, although they seem a strange bunch of guys. Here is a review of recent New York gig.
Another alt country (sort of) band I like is Tarkio the band that Colin Meloy (Decemberists) formed during a brief college interlude. Since the work is all Meloy’s and he is an undisputed genius (yeah I’m a fan) this is very classy stuff.
I think The Highwaymen will satisfy you.
Songs like The Highwayman, Desperados waiting for a train and Committed to Parkview certainly make you think and are very well-performed.
I’d also nominate the Old 97s and the Sadies (although they often veer toward psychedelia and surf music). For singer-songwriter stuff, you can’t get any better than Scott Miller (and his backing band, the Commonwealth) and Chris Knight.
Also, Drive-By Truckers are great, but that goes without saying.
**16 Horsepower **is a bit more rock, but they have deep country roots. The lead singer’s solo project Woven Hand is brilliant.
**Blalron **- this is a lot of great recommendations. Thoughts?
I love a lot of the recommendations - Neko Case immediately came to mind (and if you haven’t checked out Ghosts of the Great Highway by **Sun Kil Moon **or Feast of Wire by **Calexico **- well, it’s great, I suppose alt-country type stuff…).
While in general I am inclined to dismiss Country as a predictable genre that is not intelligent, that is really not fair. As many other posters have pointed out, I am basing my judgment on commercial country, not the “real” stuff.
Also - it depends on how you define “intelligent.” Songs like “I’m so Lonesome I could Cry” or “Cold Cold Heart” by Hank Williams, or “Crazy” or “Walkin’ After Midnight” by *Patsy Cline ** do focus on standard lovey-dovey type lyrics - but, jeez, they are little gems of crystalline songwriting perfection. Those songs are practically haiku-like *in their efficiency and emotional power…the intelligence of the artists (including Willie Nelson, who wrote Crazy) comes through…
I just discovered a guy named Ryan Bingham. He’s a 27-yr-old singer/songwriter out of Texas, and he’s opened for the Drive-By Truckers. I highly recommend his album Mescalito - he’s got a voice that sounds much older than his years and writes songs with a lot of cowboy and border-town imagery.
Thanks! I love all the country/folk/rock/alt.country singer-songwriter crew mentioned above. (Well, I’m still wishing Lucinda could sing on key.)
But some classic country is quite excellent–all that stuff that isn’t played on modern country radio. Hank Williams wrote about lost love & God–he was no Rhodes Scholar. But he could distill the essence of heartbreak; even people who’ve been to college can understand. And Willie’s early songs (“Crazy,” “Night Life” & “Funny How Time Slips Away”) are as good now as they were when he wrote them.
Also: Some country music is not meant for quiet, lyrical contemplation. It’s meant for dancing. The great Bob Wills made many recordings, but a good intro might be Asleep at the Wheel’s Ride With Bob.
I’ll second this. Virtually every cut on that album is gold. Add “Deportee” to the three you noted. All four of the Highwaymen (Cash, Kristofferson, Nelson, and Jennings) are solo artists with quite a lot of fame themselves, much of whose ouevre is not traditional country – which is also true for Garth Brooks, for Tricia Yearwood, and for Hank Williams Jr. Kristofferson’s “The Pilgrim,” Garth Brooks’ “We Shall Be Free,” “Much Too Young” and “The Beaches of Cheyenne,” Yearwood’s “The Song Remembers When” are not traditional country fare. Also remember that Kiristofferson was the writer and original singer of “Me and Bobby McGee.” And for a bit of excruciatingly soul-baring autobiography, Hank Jr.'s “Family Tradition.” Finally, a one-hit wonder that hides a devastatingly powerful message behind a sweet and melodic exterior: the Pirates of the Mississippi’s “Feed Jake.”
Hank wasn’t, but Kris Kristofferson was (Wiki link)!! 
On a live album, Willie talks about the song. He played it in rough-draft form for another musician (Bob Dylan?), who loved it. They had just one suggestion. “Maybe the chorus could be ‘Crazy’? ‘Stupid’ just doesn’t work.”
Daniel
Lots of great recommendations in this thread. To this worthy list, let me add Guy Clark. To quote allmusic:
Check out his first album, “Old No. 1,” where you’ll find such gems as “L. A. Freeway,” Desperadoes Waiting for a Train," “That Old Time Feelin’,” and “Rita Ballou.”
“The Essential Guy Clark” is a nice compendium of his work, and “Keepers” is an excellent glimpse at what one of Clark’s live shows is like, but ANY Guy Clark album will contain songs that will make you shiver as you contemplate the lyrics.
The first two verses of “That Old Time Feelin’” demonstrate Clarks craftmanship:
"That old time feelin’ goes sneakin’ down the hall,
Like an old gray cat in winter, keepin’ close to the wall.
And that old time feelin’ comes stumblin’ up the street,
Like an old salesman kickin’ the papers from his feet.
And that old time feelin’ draws circles around the block,
Like old women with no children, holdin’ hands with the clock.
And that old time feelin’ falls on its face in the park,
Like an old wino prayin’ he can make it 'till it’s dark."
I knew that–glad somebody got it. Kris has writtens some fine songs, but he’s no Hank Williams. (And I’m sure he’d agree.)
What?!? No love for Kinky Friedman?
That’s from “They Ain’t Makin’ Jews Like Jesus Anymore”–or you might like "“Get Your Biscuits In The Oven and Your Buns In Bed” or “Ride’ em Jewboy” (a tribute to the victims of the Holocaust).
Oh man - great call! His song “Stuff that Works” is deceptively brilliant. It’s a song about loving reliable tools/things he uses, like a work shirt that hangs on a peg in his closet. It starts out sounding, I dunno, like a Chevy ad or something, but his lyrics dig into the concept of simple things you can believe in and hold onto in a non-sentimental way. It embodies the honest feeling that companies like Chevy attempt to co-opt and never really do…
And yeah, **BB **- KK would be the first to admit that very, very few are in Hank’s league. I might point to Willie, maybe Dolly Parton - not many. I am not deeply versed in first-gen Country songwriters, so I wouldn’t be the person to put that list together…
Took mine. I LOVE Junior Brown. If you ever, ever get a chance to see him in person, go. He plays an instrument he created, which he calls a guit-steel. He’s an absolute virtuouso. He also performs with just one other person, a drummer, although I think sometimes his wife plays guitar with him too.
This isn’t what you’re looking for, but I just have to throw ol’ George Jones out there. I think he is just plain fun. Half of his moaning old drunk country soungs sound serious, but I’m not sure he EVER is. For example: “Drive Me to Drink.”
And I defy anyone to watch the movie Coal Miner’s Daughter and not come away a fan. I love her song Fist City. Of course, it may be an acquired taste.
I’m about the last person anyone would suspect of liking country music, but I have these on my iPod and love 'em. Good tunes and smart lyrics:
Brad Paisley, “I’m Gonna Miss Her”
Martina McBride, “Independence Day” and “In My Daughter’s Eyes”
Phil Vassar, “American Child”
Garth Brooks, “We Shall Be Free”
Trace Adkins, “Swing”
Blake Shelton, “The More I Drink”
Reba McEntire, “Why Haven’t I Heard From You”
Johnny Cash, “Rock Island Line” and “Folsom Prison Blues”
k.d. lang, “Little Patch of Heaven”
Junior Brown is a freakin’ guitar monster.
If this thread were about the musical talent of country players - well, that’s simply not an issue. Some twangers put most rock players to shame. Chet Atkins, Vince Gill, Hoyt Axton, Jerry Reed - we may remember these guys saying “aw shucks” from bad 60’s TV Shows or Smokey and the Bandit movies - but don’t kid yourself, these guys are total guitar virtuosos…and Junior Brown is in that category.
Mark Knopfler worshipped the ground Chet walked on…
Good call on Guy Clark. “The Randall Knife” is one of my favorite songs of all time.
I’ve unfortunately only seen Junior Brown live once, but it was easily in my top five shows of all time. I knew I’d be in for a good one when Junior made an elaborate show of putting in a pair of earplugs before launching into his first song. He draws an interesting crowd, too, by Lexington, KY standards. Lots of your typical “alt-country” types, but almost all the good local punk and metal guitarists were there as well as a sizable contingent from the local Mexican community (Junior’s bilingual, so that makes sense).