100 Best Country Albums of the 2000s: Part Five (19–1)

And so we’ve arrived at the best of the best. The 19 greatest country albums of the 2000s. This has been a lot of fun and one of the hardest things to cultivate, but it’s been worth it. Hope you all have enjoyed it!

19.) I’m Not The Devil
Artist: Cody Jinks
Producer: Joshua Thompson

Sturgill, Isbell, Stapleton. They’re great at what they do, but they’re also interested in branching out beyond their typical boundaries. Which is fine. But it’s always great when artists like Whitey Morgan and Cody Jinks are just interested in recording down-the-line, stone-cold country music. The genre needs variety. And the part of the genre that’s holding firm onto the days of country’s past is just as important as those looking to innovate. Cody Jinks isn’t doing anything particularly groundbreaking with his music. He’s just *that* good he demands to be heard. The title track is an outlaw country anthem. Jinks’ cover of Merle’s “The Way I Am” is sharp and poignant. And “Church at Gaylor Creek” is an instant classic using familiar country themes.

18.) Up on the Ridge
Artist: Dierks Bentley
Producer: Jon Randall Stewart

After releasing Feel That Fire, Dierks was feeling burnt out. Ask him, and I’d bet he’d tell you Feel That Fire just wasn’t up to his standards. So what did he do? Get back to his roots. His serious roots. His bluegrass roots. Guest artists include The Punch Brothers, Del McCoury, Miranda Lambert, and Jamey Johnson along with Kris Kristofferson appearing on a cover of his “Bottle to the Bottom.” Dierks also covers Bob Dylan’s “Señor (Tales of Yankee Power)” and U2’s “Pride (In The Name of Love).” The album could certainly be classified as progressive bluegrass, and it’s a perfect melding of Dierks’ country, rock, and bluegrass influences. Remember, he used to hang around The Station Inn when he came to town. His credentials are serious. Just listen to “Down in the Mine.” Up on the Ridge signaled the birth of the second phase of Dierks’ career.

17.) Turnpike Troubadours
Artist: Turnpike Troubadours
Producers: Ryan Engleman and Matt Wright

Evan Felker’s songwriting, already some of the best in music, reached new heights with the band’s self-titled album. The poignant songwriting, combined with a fuller production and even bigger emphasis on the band, resulted in one of the best records of the 2000s. “The Bird Hunters” is magnificent with songwriting that’s worthy for a Townes van Zandt or Kristofferson. “The Mercury” is somehow both a drinking-party song and a story song. Kyle Nix’s fiddle shines across the album, and Ryan Engleman has developed a defining guitar sound for the band.

16.) Colter Wall
Artist: Colter Wall
Producer: Dave Cobb

Colter Wall is this generation’s Johnny Cash. He has been since he released his first EP. At his heart, he’s a folk singer, and maybe that’s where biggest difference between him and Johnny arises. Johnny could go electric and rock. But Colter is fine with keeping it simple. And that’s fine for the rest of us. He first gained prominence thanks to his deep, distinctive voice. But its his songwriting that really shines. Many of the songs on his self-titled debut are autobiographical, which helps the album become even more poignant. “Motorcycle” is perfectly nihilist, while “Thirteen Silver Dollars” is so clever in its simplicity. “Kate McCannon” is something the Man in Black would have recorded. And his beautiful cover of “Fraulein” with Tyler Childers sends chills up the back.

15.) Traveller
Artist: Chris Stapleton
Producer: Dave Cobb

Traveller is the most important album of the 21st Century. I’m sure of that. Stapleton simultaneously opened doors for both the underground and mainstream worlds. This was music for people who were tired of bro-country. Tired of pop-country. Tired of immature lyrics and a watered-down sound. Traveller allowed Stapleton to become a household name in music. But this album isn’t included here just because of its influence. Much of the sound comes straight out of the 70s, and Stapleton’s songwriting is absurdly good.

14.) Junky Star
Artist: Ryan Bingham
Producer: T. Bone Burnett

Bingham’s songwriting is just on a completely different level than any other artist in music. When Bingham has something to say, you best listen. Junky Star is a little quieter than his first two albums. A little sparser and more resigned to the difficulties of life. The two standout tracks are “Depression” and “Hallelujah.” “Hallelujah” in particular is special. Words can’t do justice to the themes and instrumentation. The title-track deserves a mention as well. Bingham is just so good at channeling Townes-esque lines and turn-of-phrases.

13.) Sinners Like Me
Artist: Eric Church
Producer: Jay Joyce

The album that started it all and launched the career of the greatest artist of our generation. It foreshadowed much of what was to come from Chief over the next decade. It was rowdy. It was different. It was totally refreshing for a mainstream country music that was watered down with poppy and sugary production. Church channeled the intersection of Merle Haggard and Steve Earle. Plenty of country with plenty of heartland rock. The title track is a rousing outlaw anthem. “These Boots” is still the essential live track. “Lightning” is breath-taking. So many of the songs on Sinners Like Me shaped how Church would make his career.

12.) The Guitar Song
Artist: Jamey Johnson
Producers: Arlis Albritton, Wayd Battle, Jim Brown, T.W. Cargile, Kevin Grant, “Cowboy” Eddie Long, Dave McAfee, and Jamey Johnson

Ah, the double album. But in this case it works. Especially considering how it looks like we won’t be getting new music from Jamey anytime soon. The album is divided into black and white. The black record contains heartbreak and country drinking songs like the covers of “Set ’Em Up Joe” and “Mental Revenge.” The white album, conversely, while not totally carefree, contains softer, more redemptive songs like Jamey’s “Macon” and “My Way To You.” A great follow-up to That Lonesome Song, considering the expectations were sky high.

11.) High Top Mountain
Artist: Sturgill Simpson
Producer: Dave Cobb

A game-changing album. Sturgill would really stretch his wings after his debut, but High Top Mountain will forever remain his most important and best album, even if he and many won’t ever admit it. The album was released during the heyday of bro-country. And it was exactly what many country fans were waiting for. Look, Sturgill can try as hard he wants to get away from his country roots. He can go record Motown, rock and roll, or frickin’ jazz, and he’d make it awesome. But at the end of the day, country music is what Sturgill does best. And High Top Mountain alone makes him a legend.

10.) Diamonds & Gasoline
Artist: Turnpike Troubadours
Producer: Mike McClure and Turnpike Troubadours

The album that introduced the best damn band in music to the world. The songwriting is exceptional. The instrumentation is more understated when compared to their more recent albums, but it’s still better than anything else around. “The Funeral” is a must-listen. “Long Hot Summer Days” has become a fan favorite. And “Every Girl” is pure poetry. Turnpike is a transcendent band. Evan Felker’s lyrics recall Hemingway, Faulkner, or McMurtry, depending on the song. And yet the lyrics are somehow immensely relatable despite their literary weight. The band itself is on fire, with Kyle Nix on fiddle particularly deserving of a mention. All of this was on display already on Diamonds & Gasoline.

9.) Roadhouse Sun
Artist: Ryan Bingham
Producer: Marc Ford

Ryan Bingham is *the* artist who has best captured that intersection between Townes van Zandt-esque songwriting and Uncle Tupelo-esque punk country. And nowhere is that more evident than on Roadhouse Sun. “Dylan’s Hard Rain” is just phenomenal, with references to both Dylan (obviously), modern times, and some lines about life. “Tell My Mother I Miss Her So” is an immensely fun rambler’s anthem. But it’s his ability to create a theme with each album that makes Bingham such an incredible artist. While not as carefree as Fear and Saturday Night, Roadhouse Sun nonetheless is a little more stress-free than Junky Star and Tomorrowland. It’s built around the troubadour.

8.) Desperate Man
Artist: Eric Church
Producer: Jay Joyce

I wrote extensively on Desperate Man when it was released. Suffice to say, it’s the album Chief has been waiting his entire career to make. It’s different and certainly not for everyone. But his long-time fans never had a doubt the he’d release an album like this. There’s a distinct Stones influence across the record and not just from the Richards-esque guitar. The themes, the battles between good and evil. It’s what the Stones spent the early 70s singing about. But in typical Chief fashion, Church included songs like “Some Of It” and “Hippie Radio” for fans more inclined to his early material. Special mention for “Jukebox and A Bar,” which is a classic barroom drinking song.

7.) Lovesick, Broke and Drifin’
Artist: Hank Williams III
Producer: Hank Williams III and Joe Funderburk 

Before Sturgill. Before Cody Jinks. Hell, before Whitey Morgan. There was one artist who did more for the underground community than any other. Did more to open doors and remind fans that there was an alternate out there to the mainstream. Shelton Hank Williams. Hank III. Lovesick, Broke and Driftin’ is the essential underground country album. It may not be as extensive as Straight to Hell, but it’s the the most succinct album to define the modern underground country movement. The great thing about Hank III is his ability write and record material that sounds like a cover of his grandfather (the title track, “5 Shots of Whiskey) and sounds very much like his own (“7 Months, 39 Days,” “Trashville”). Kayton Roberts also shines on steel guitar.

6.) Way Out West
Artist: Marty Stuart & His Fabulous Superlatives
Producer: Mike Campbell

Concept albums have a storied history in country music. As does the American West. Marty Stuart executes both perfectly with Way Out West. Stories about dying in the desert, tripping on blue pills, green Aliens, running away to Mexico, wistful ballads for lost love. The instrumentation is top-notch as well. Indeed, you may not find a better band in music than Marty’s. One of two things has to be true to really *get* this album. One, you’re fascinated with the mythology of the West. Or, two, you have spent time in the West. If at least one of those two things is true, you’ll immediately fall in love with Way Out West. There’s really a mood you can get into while listening. You’re transported immediately to the desert. You’re there with Marty.

5.) Chief
Artist: Eric Church
Producer: Jay Joyce

If Mr. Misunderstood was the album that launched Eric Church to become a transcendent artist in music as a whole, Chief was the album that launched the biggest phase of Church’s country career. With smash radio singles like “Springsteen” and “Drink In My Hand” and deep album cuts like “Over When It’s Over” and “Hungover and Hard Up,” Chief is the album Church spent the first part of his career preparing for. Everything was about to get a whole lot bigger for Church. This was the album that rallied and expanded Church’s fan-base even more.

4.) That Lonesome Song
Artist: Jamey Johnson
Producers: Dave Cobb, Jamey Johnson, and The Kent Hardly Playboys

Pure, stone-cold, uncut country music. Outlaw anthems. Barroom weepers. Clever melodies and hooks. The acclaim for That Lonesome Song cannot be understated. Johnson’s deep baritone just lends itself to classic country music. The songs themselves are country to the core. They’re not overly complicated. Johnson uses the Haggard formula to a T. Sing about life. Sing about being down. Sing about being drinking. It seem easy to do. Until you realize not many artists can do it. The beauty of Jamey Johnson’s music can be found in its simplicity.

3.) Tough All Over
Artist: Gary Allan
Producers: Mark Wright and Gary Allan

If you’re going to listen to Tough All Over, you better be ready to cry and be in your feelings. Recorded and released just a year after his wife of three years committed suicide, Tough All Over is immensely dark and painful. Song after song just hits you like a ton of bricks- especially the one-two punch of “Ring” and “Promise Broken.” Even the one bright spot on the album, “Life Ain’t Always Beautiful,” carries with it a somber and sobering message. A master-piece.

2.) Mescalito
Artist: Ryan Bingham
Producer: Marc Ford Lucas Hoge

Ryan Bingham is the definition of a troubadour. Mescalito, Bingham’s first studio album, really exemplifies all of Bingham’s best traits. It’s not as focused or cultivated as his later albums, but Mescalito succeeds so well because of Bingham’s incredible songwriting and raspy voice. The album kicks off immediately with “Southside of Heaven,” a beautiful rambler’s romp. “Long Way From Georgia” is one of Bingham’s most underrated works, with it proving to be at least somewhat autobiographical. “Sunrise” is a fan-favorite in concert, and “Ever Wonder Why” will knock you of your feet. With every song on the album, it’s like you’re looking down with a glass of whiskey in your hands and a bunch of dirt and sand on your boots.

1.) Midnight Motel
Artist: Jack Ingram
Producer: Jon Randall

And at number one, it’s Jack Ingram with Midnight Motel! After a relatively brief time in Nashville with a major label, Ingram said screw it and returned to Texas. His return to recording was well worth the wait. Midnight Motel works because the album flows so smoothly. There’s banter in between songs. “Blaine’s Ferris Wheel” kicks off with a brief story from Jack about what he’s singing about. “I’m Drinking Through It” is a wonderful drinking song. “Nothing to Fix” contains considerable wisdom, especially for songwriters; the Guy Clark influence is strong. And “It’s Always Gonna Rain” shines with some beautiful, melancholy instrumentation. The songs by themselves, while definitely great, are not necessarily brilliant. But it’s the way the songs work together plus Ingram’s attitude that makes Midnight Motel the best album of the 2000s.

Thanks for reading!