Emmylou Harris
Mary Chapin Carpenter
Rosanne Cash
Lucinda Williams
Hey, I saw him in Lexington! 
There’s always Townes Van Zandt – hell, I almost prefer his rambling intro to “Pancho and Lefty” to the song itself, and it’s a damn good song.
And how about The Silver Hearts (youtube video)? The configuration I saw them in a couple of years ago included 11 members, with a sousaphone for a bass. They also threw a theremin and a saw into a few songs. I hope they come back my way soon.
Here’s my list of favorite country(ish) albums, all of which I’d consider “intelligent country” and some of which have already been mentioned (with YouTube links to sample songs):
Drive-By Truckers - Decoration Day (“The Deeper In” - poor quality live video, but great song)
Drivin’ ‘n’ Cryin’ - Mystery Road (“Honeysuckle Blue”)
Iron & Wine/Calexico - In the Reins (“He Lays In The Reins”)
Gillian Welch - Time (The Revelator) (“Time (The Revelator)”)
Lyle Lovett - Joshua Judges Ruth (“She’s Already Made Up Her Mind”)
Neko Case - The Tigers have Spoken (“If You Knew”)
Robbie Fulks - Georgia Hard (“Georgia Hard”)
Ryan Adams - Heartbreaker (“Come Pick Me Up”)
Son Volt - Trace (“Tear Stained Eye”)
Sun Kil Moon - Ghosts of the Great Highway (“Carry Me Ohio”)
Tarkio - Sea Songs for Landlocked Sailors (“Tristan and Iseult”)
Uncle Tupelo - No Depression (“Graveyard Shift” - poor quality live recording, unfortunately)
Whiskeytown - Faithless Street (“Drank Like a River” - there’s cussin’ up front, so mind your co-workers)
Jesse Dayton. Is he country, alt-country or rockabilly? It doesn’t matter, the boy writes a great song, plays a mean guitar and has just enough twang to make me homesick for Texas.
Where? The wife and I saw him at the Dame about three years ago.
WTF?! File that under “Things I Wouldn’t Have Guessed With A PhD In Guessing And A Guess-Generating Machine.”
Here’s another vote for Jimmie Dale Gilmore, Old 97’s, and Townes Van Zandt.
And I’d add Kelly Hogan to the mix. She’s awesome.
Listen to some Waylon Jennings, my friend. Some thoughtful and interesting lyrics to be found in his catalogue. Dreaming My Dreams, for example. Or Amanda.
Merle Haggard has also done some fine work. There is an excellent Merle Haggard tribute album featuring some of his best songs: Tulare Dust
I strongly second this suggestion. Their album Folklore is nothing short of sublime.
I’ld also like to add William Elliot Whitmore. http://www.youtube.com/watch?v=ej6hCIB6Z7c one of my favorite songs.
Another “more Americana” suggestion: Jim White.
Check out the soundtrack to “Search for the Wrong Eyed Jesus.”
Jim White is great (although I like his second and third albums more).
Jolie Holland is another good one who might or might not be classified as country.
Not sure if you’d class it exactly as “intelligent,” but C. W. McCall’s stuff isn’t about gettin’ drunk and his dog dyin’ and his wife leavin’. His music is part “country trucker rap” (in the style of “Convoy”), part love for nature and the wilderness, and part nostalgia. Oh, and songs about cannibals (“Comin’ Back for More”).
Surprisingly, I don’t think Kelly Willis has been mentioned yet.
Fighting ignorance is our business.
The late Hoyt Axton. “Della and the Dealer” and “Boney Fingers” are two of his better known songs, but he was one talented songwriter/singer.
I don’t know if you’d call it “intelligent”, but you might try Charlie Haden’s Family and Friends - Rambling Boy.
It’s a great collection of what I’d call Americana music performed by an impressive gang of Haden’s relatives and friends. If you enjoyed the soundtrack to “O Brother, Where Art Thou?”, I think you’ll like “Ramblin’ Boy”.
I think I’ll nominate Brad Paisley as the frontrunner of the current crop of radio stars. He doesn’t take himself too seriously, or the business as a whole. He just goes out there and has fun - albeit with a cowboy hat and twangy guitar.
Songs like: (YouTube links)
I’m Gonna Miss Her
Online (with a great Shatner cameo)
(both mentioned already)
Alcohol
Celebrity (nice American Idol parody/Shatner fun/Hollywood point and laugh)
I’m Still a Guy
Ticks
Mud on the Tires
Letter to Me
The last three get a little closer to standard country, but are still pretty dang good. Thanks for making me realize that I need to track down more of his stuff and make me fight my bank account over going to his tour later this month :mad: 
And this differs from other genres of popular music… how?
MOST popular music covers a very small range of subjects. 99% of pop/rock music falls into one of the following categories:
- I love him/her so much!
- I USED to love him/her so much!
- Let’s dance!
- Let’s party!
- I’m really horny!
- I’m really cool.
Obviously, there are lyricists who break the mold, but you get my drift, and I hope you’ll concede the point. Country music lyrics aren’t noticeably more limited in scope than rock lyrics.
One of the best songwriters of the past 50 years, and once widely touted as “the next Bob Dylan” (along with about ten other guys), is John Prine. He defies labels, really, but probably fits most comfortably somewhere between country and folk, like Woody Guthrie.
You won’t find more intelligent songs than Sam Stone, Paradise, Mexican Home, Angel from Montgomery, Donald and Lydia, Hello in There, Souvenirs, and about a hundred other great songs.
His must-have album is his eponymous debut in 1971. It’s one of my all-time favorite albums. Anyone who likes country/folk (or any other music, really), should listen to this album. A front-to-back collection of brilliant songs.
Here’s Sam Stone on YouTube. Give it a listen.