50 Greatest Country Artists of All-Time: Part Three (30–21)

Nathan Kanuch
Jun 25 · 8 min read

We’ll get right back to it!

30.) Brad Paisley

We’ll look back one day on Brad Paisley’s career and wonder how we didn’t appreciate him as much as we should’ve while he was a star. It’s not that he hasn’t achieved critical acclaim or released number one single after number one single. It’s that Paisley’s career longevity has snuck up on us. His brilliant mix of serious and funny songs seemed to keep him young as an artist until, suddenly, he had been a hit machine for almost twenty years. Something I’ve always appreciated about Brad Paisley is his pattern of recording courageous albums that venture out of typical country themes (American Saturday Night and Wheelhouse) but then following them up with strong, traditional-minded country music (This Is Country Music and Moonshine in the Trunk). Brad Paisley is an outlaw, make no mistake of that. The next part of his career will be just as exciting as his superstardom.

Essesntial songs: “Whiskey Lullaby,” “You’ll Never Leave Harlan Alive,” “We Danced,” “I’m Gonna Miss Her (The Fishin’ Song),” “Mud On The Tires,” “Officially Alive,” “Online,” “Waitin’ On a Woman,” “Welcome To The Future,” “This Is Country Music,” “Last Time For Everything,” and “Bucked Off”
Essential albums: Part II, Time Well Wasted, American Saturday Night, Wheelhouse, and This Is Country Music

29.) Jerry Reed

One of the coolest things about hearing a Jerry Reed song is knowing it’s one of his songs just a couple guitar licks in. Reed was a trailblazer. He played his music and went into acting, unabashedly just by being himself- a guitar’ pickin country boy. Elvis covered his songs and had him play on some of his sessions. Jerry Reed, like Brad Paisley, knew how to find the perfect balance of novelty songs and more serious material. A truly great ambassador for the country genre.

Essential songs: “Guitar Man,” “East Bound and Down,” “Amos Moses,” “When You’re Hot, You’re Hot,” “You Took All the Ramblin’ Out of Me,” and “She Got The Goldmine (I Got the Shaft)”
Essential albums: The Unbelievable Guitar and Voice of Jerry Reed, When You’re Hot, You’re Hot, and The Essential Jerry Reed

28.) Steve Earle

Steve Earle has worn many coats and successfully recorded several types of country music. He can play bluegrass. He can play outlaw country. He can play country rock. He can write a song up there with the best to ever do it. Earle moved to Nashville at the age of just 19, palling around with Rodney Crowell, Guy Clark, and once back in Texas, Townes van Zandt. Steve Earle had a wildly successful start to his career before almost dying in the early 90s, going through a recovery from heroin, and then experiencing a career renaissance with some of the best material of his career since. No topic is off limits for Earle to write a song about.

Essential songs: “Guitar Town,” “Someday,” “Good Ol’ Boy (Gettin’ Tough),” “The Week of Living Dangerously,” “Copperhead Road,” “The Devil’s Right Hand,” “Johnny Come Lately,” “Ben McCullough,” “Feel Alright,” “Valentine’s Day,” “Billy and Bonnie,” “The Mountain,” “Lonelier Than This,” “The Girl On The Mountain”
Essential albums: Guitar Town, Copperhead Road, I Feel Alright, Townes, and So You Wannabe an Outlaw

27.) Eric Church

Renegade. Rocker. Outlaw. Spark plug for a different take on mainstream country. Eric Church has seen it all. He’s been black-balled, forced to play rock clubs. He’s been written off. He’s faced the threat of releasing a make or break single. And he’s beaten it all and left all the doubters in a ditch. Eric Church isn’t content to record and release his type of country to a small community. He wants his fans to respond in a big way. He doesn’t need the Nashville machine. But the Nashville machine needs him. Chief’s live shows are an inherant part of the mystique and one of the many reasons the 42 year old is already rated so high up on the list.

Essential songs: “These Boots,” “Sinners Like Me,” “Two Pink Lines,” “Lightning,” “Carolina,” “Lotta Boot Left to Fill,” “Smoke A Little Smoke,” “For Those I’ve Loved,” “Drink in My Hand,” “Creepin’,” “Springsteen,” “The Outsiders,” “Dark Side,” “A Man Who Was Gonna Die Young,” “Mr. Misunderstood,” “Mistress Named Music,” “Knives of New Orleans,” “Record Year,” “Desperate Man,” “Some of It,” and “The Snake”
Essential albums: Sinners Like Me, Chief, Mr. Misunderstood, and Desperate Man

26.) Roger Miller

Perhaps Roger Miller’s greatest legacy was the respect he gave to young, renegade artists like Willie Nelson and Kris Kristofferson. But that would still be selling Miller short. He was a hell of a songwriter himself before he became a star and could sing the silliest song in the world and still have the audience captivated. His scat singing was organized chaos, and his voice has to be one of the most memorable in country music history.

Essential songs: “Dang Me,” “Chug-a-Lug,” “King of the Road,” “England Swings,” “Me and Bobby McGee,” and “Whistle Stop”
Essential albums: Roger and Out, The 3rd Time Around, and A Trip in the Country

25.) Hank Williams Jr.

Hank Jr. today, like the modern incarnation of Lynyrd Skynyrd, has been reduced to parody (with a little help from his own comments, mind). And yet we must not let Bocephus’ true legacy die. Everyone in Nashville wanted him to sing music like his Dad. And he did for several years. Until the fall off Ajax Peak in Montana. He began wearing sunglasses and a hat (mostly to cover up his injuries, but I’m sure an element of image was involved as well). Most importantly, Hank Jr. began recording music that would become his own. There’s simply no other artist like him. He took the outlaw movement led by Waylon and Willie, threw his own flavor in, and became a legend. Mainstream Nashville was finally forced to recognize him in the late 80s, awarding him with Entertainer of the Year and Best Male Vocalist several times. Hank Jr.’s songwriting is also an underrated aspect of his career. He may not have written his hits in the same way as his Dad. But it’s about just as effective.

Essential songs: “Family Tradition,” “Whiskey Bent and Hell Bound,” “Old Habits,” “Dixie On My Mind,” “All My Rowdy Friends (Have Settled Down),” “A Country Boy Can Survive,” “Leave Them Boys Alone,” “Country State of Mind,” “Born to Boogie,” and “Whiskey On Ice”
Essential albums: Hank Williams Jr. and Friends, Family Tradition, Whiskey Bent and Hell Bound, The Pressure Is On, High Notes, and 127 Rose Avenue

24.) Porter Wagoner

“He wore a long purple coat, covered in wheels…” There’s so much I could say about Porter and his brilliant legacy in country music. His championing of Dolly Parton. His recording of one of the first concept albums in country music (The Cold Hard Facts of Life). His steadfast defense of traditional country music. His hundreds of appearances on the Grand Ole Opry. All I’ll say is, Porter, we miss you. Thank you for everything. I challenge anyone to get to the last verse of “Green, Green Grass of Home” without getting goosebumps.

Essential songs: “Green, Green Grass of Home,” “A Satisfied Mind,” “Misery Loves Company,” “The Carroll County Accident,” and “Sorrow On The Rocks”
Essential albums: The Cold Hard Facts of Life, Skid Row Joe-Down in the Alley, and The Essential Porter Wagoner

23.) Dwight Yoakam

A country music icon in every sense of the word. At a time when the genre was recovering from the Urban Cowboy phenomenon, Dwight traced his roots directly back to Buck Owens and the Bakersfield Sound. No B.S. No compromises. Just music as pure as one could get. Dwight Yoakam is the first link between punk bands like X and The Blasters and country music itself. A writer of many of his own hits, Dwight’s partnership with guitarist and producer Pete Anderson resulted in musical genius. Like Jerry Reed, Dwight Yoakam was not ashamed about his background in country music while venturing into acting. Another great ambassador for the greatest genre in the world.

Essential songs: “Guitars, Cadillacs,” “Little Ways,” “Streets of Bakersfield” (with Buck Owens), “I Sang Dixie,” “Buenas Noches from a Lonely Room,” “Turn It On, Turn It Up, Turn Me Loose,” “A Thousand Miles From Nowhere,” “Fast As You,” and “Purple Rain”
Essential albums: Guitars, Cadillacs, Etc., Etc., Hillbilly Deluxe, This Time, 3 Pears, and Swimmin’ Pools, Movie Stars

22.) Kitty Wells

At a time, when women are struggling more than ever to get played on country radio, it’s important to remember the pioneers of the past for inspiration. Kitty Wells is the ultimate pioneer. After all, Kitty scored the first ever number one hit by a female on the country charts with “It Wasn’t God Who Made Honky Tonk Angels.” And yet we shouldn’t just look at the milestones Kitty set. Her voice was smooth and tender yet confident and tough, setting the bar for future legends like Loretta Lynn.

Essential songs: “It Wasn’t God Who Made Honky Tonk Angels,” “Release Me,” “I Can’t Stop Loving You,” “Jealousy,” and “Heartbreak U.S.A”
Essential albums: The Kitty Wells Story, Queen of the Honky Tonk Street, and 20th Century Masters- The Millenium Collection

21.) Uncle Tupelo

Alternative Country legends. Trend-setters. The *standard* for recording country music outside the constraints of Nashville. Jay Farrar and Jeff Tweedy found a one-in-a-million sound when they formed Uncle Tupelo. Fusing together the hard punk of bands like The Clash and the traditional country of Hank Williams, Uncle Tupelo spawned an entire movement, no matter how much the former members try to downplay their legacy. Simply put (and this is no exaggeration), artists as diverse as Old 97s, Hank Williams III, Jason Isbell, Shooter Jennings, Whitey Morgan, Sturgill Simpson, Tyler Childers, Cody Jinks, and other modern pioneers of alternative country would not have had the platform they found without Uncle Tupelo. The band knocked down doors and also gave us two fantastic bands when Farrar and Tweedy couldn’t work together anymore. Farrar (my personal favorite) formed Son Volt and continued the path of Uncle Tupelo, while Tweedy chased some stardom and formed Wilco. Words will never be able to describe what Uncle Tupelo accomplished for Alt-Country.

Essential songs: “Graveyard Shift,” “No Depression,” “Factory Belt,” “Whiskey Bottle,” “Screen Door,” “Still Be Around,” “Punch Drunk,” “Grindstone,” “Satan, Your Kingdom Must Come Down,” “Moonshiner,” “Slate,” “Acuff-Rose,” “The Long Cut,” and “Chickamauga”
Essential albums: All four of them- No Depression, Still Feel Gone, March 16–20, 1992, and Anodyne

Shore2Shore Country

A different kind of look at country music. Opinions and historical examinations of America’s greatest genre along with updates on the current state of country music.

Nathan Kanuch

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Graduate of W&J College 2016.

Shore2Shore Country

A different kind of look at country music. Opinions and historical examinations of America’s greatest genre along with updates on the current state of country music.