The 20 Most Underrated Country Stars Of All Time
Country music has produced some big stars over the years who’ve gone on to enjoy major success: Dolly Parton and Willie Nelson are just a couple of examples. But while those figures have dominated the spotlight, a whole group of unsung artists have also been contributing to the genre for decades. And it’s time they got their due! So grab your cowboy hats and rhinestones: we’re about to run down the 20 most underrated country stars to ever take to the microphone.
1. Townes Van Zandt
Aside from having a name that just screamed “country music,” Townes Van Zandt was a true talent who had the tools to dominate the genre. He fit outlaw country like a glove.
The singer-songwriter produced several melancholic tracks across his career that wouldn’t have sounded out of place in the oeuvre of Neil Young or Bob Dylan. We’d recommend “Waiting Around To Die” and “Lungs” if you fancy a good sob!
Fear of fame?
But why wasn’t Van Zandt a more mainstream name in the genre? Well, part of it was down to his own reluctance to pursue fame. He feared what it could’ve done to his career. That’s why Van Zandt didn’t want to work with Dylan whenever the chance arose, despite admiring him.
Mind you, there were other factors at play here, too. For once, the artist had a history of struggling against serious substance abuse issues throughout his life, prior to his death on New Year’s Day in 1997.
2. The Louvin Brothers
Although their names might not carry the weight of some of their country contemporaries, one thing can’t be denied about Charlie and Ira Louvin. They were true pioneers of the scene throughout the 1950s.
Known simply as The Louvin Brothers, their wonderful harmonies inspired lots of future figures within the genre. Tracks such as “When I Stop Dreaming,” “Knoxville Girl,” and “I Don’t Believe You’ve Met My Baby” are stone-cold classics!
Elvis was a huge fan!
The band’s gospel influences can’t be ignored, either, and a certain Elvis Presley loved that side of their work! Yet The Louvin Brothers could’ve been even bigger stars at the height of their fame. The siblings recorded a host of songs in the past that they didn’t actually release.
Instead, other singers took the tracks on: Roy Acuff’s “Streamline Heartbreaker” and Carl Story’s “Love and Wealth” were just a couple of examples. Ira and Charlie’s original versions finally came out via a compilation record in 2018.
3. Gillian Welch
If you’re not familiar with Gillian Welch, then the following description should give you some insight into her style. The WKNC-FM radio website joked that she’s a “300-year-old ghost who makes music.”
It’s weirdly accurate, though! Welch’s hauntingly beautiful tracks are both timely and timeless: a balancing act that few Appalachian folk stars can match. The Harrow & The Harvest is a great place to start if you’re curious.
“Too rootsy and traditional”
Yet it could be argued that the very things that make Welch unique are also stopping her from becoming a more mainstream star. As WKNC-FM put it, she’s “too rootsy and traditional for Pitchfork but too raw and unfiltered for the Grand Ole Opry.”
In other words, she’s operating in a pretty narrow niche! Something tells us that fans of Welch’s dark, poetic output wouldn’t want that to change anytime soon, even if it means she’ll stay under the radar.
4. Steve Earle
How many artists can say that they cranked out 21 albums across 26 years that all maintained the same high quality? And after a tough sabbatical no less? Well, step forward Steve Earle!
Since dropping his first record in 1986 the singer-songwriter has garnered quite the reputation in country music circles. Earle’s fluid style and prolific rate of output has allowed him to experiment in various genres, ranging from folk to alt-country, and he’s rarely looked out of place.
Personal struggles
But despite his undeniable talent, why is Earle such an underrated figure with mainstream country fans? In truth, there may be a couple of reasons. The first ties back to the personal struggles he experienced in the early part of his career.
Earle was addicted to drugs and alcohol during that spell, which led to his arrest and subsequent sabbatical. That’s still held against him in some quarters. Then, there’s his musical flexibility, which makes him a tough artist to pigeon-hole.
5. Lucinda Williams
A bona fide veteran, Lucinda Williams has been knocking out her unique blend of rock, blues, and country since her first album dropped in 1979. And it’s earned her plenty of success.
The musician has three Grammy Awards to her name, which is no mean feat! She’s still performing on stage as well, kicking off the European leg of her tour at the end of February 2024.
The downside of consistency?
As commendable as all that is, though, Williams has often been overlooked by the mainstream. To give you an example, when she dropped her latest record in 2014, it was hailed by some as one of her best efforts.
Yet many of the major music publications, including Rolling Stone, failed to give it a review. Broadly speaking, Pitchfork put forward the case that the consistent, almost expected quality of Williams’ music causes it to get lost in the shuffle. That’s a strange problem to have!
6. Hank Williams III
As the grandson of the legendary Hank Williams Sr., Hank Williams III had a lot to live up to at the start of his career. He was a third-generation country musician, following in the footsteps of his grandfather and dad.
Yet he had no interest in simply copying their styles. Williams went on to become something of a revolutionary figure in the genre: he proved country with a punk and metal edge could absolutely work.
Inescapable shadows?
Why is Williams so underrated nowadays, then? Well, it’s possible that a lack of recent activity has played a role in that. His last album dropped back in 2017 and even that was just a greatest hits release.
Plus, we can’t forget about the, ahem, shadows that his grandfather — who passed away in 1953 — and his dad continue to cast. Regardless of Williams’ accomplishments, some believe that he still hasn’t escaped them.
7. Emmylou Harris
Boasting a voice that’s both powerful and sweet, Emmylou Harris has enjoyed quite the career in country music. She’s dropped more than 20 solo albums and won 13 Grammy Awards since getting started in 1969.
In addition to that, Harris has collaborated with some huge names in the genre across the years. From Linda Ronstadt and Dolly Parton to Gram Parsons, it’s an impressive list!
What could’ve been
But Harris herself isn’t part of that heavyweight class, despite having the talent to merit it. Perhaps things would’ve been different if The Ballad of Sally Rose had been a bigger hit in 1985? The concept album failed to capture the attention of country fans at large, even though it was critically acclaimed.
The record did receive its flowers upon a special re-release in 2018 yet it does make you wonder. Where could Harris be today if the public had recognized that album as her magnum opus nearly 40 years ago?
8. Ricky Skaggs
Ricky Skaggs is as multi-talented as they come in the world of country music. Not only does he have a great voice, but he’s something of a virtuoso with the mandolin as well.
Skaggs played a huge role in bringing classic country sounds back in the 1980s amid the rise of the countrypolitan style. No fewer than 11 of his tracks reached the top of the charts during that period, including the classic “Country Boy.”
Falling victim to country-pop
Everything changed going into the 1990s, though. Thanks to the likes of Shania Twain and Garth Brooks, country-pop became the new in thing, leaving Skaggs in the dust. His brand of country just wasn’t hitting the right notes any more as far as his audience was concerned.
And while he did eventually pivot into bluegrass later that decade, we can’t help but wonder what could’ve been. Would Skaggs be in the conversation as an all-time great if his stellar ’80s run hadn’t come to an end?
9. The Chicks (formerly Dixie Chicks)
When it comes to naming eye-catching bands, the group formerly known as the Dixie Chicks have to be in the conversation. Since forming at the end of the 1980s, they’ve taken the music world by storm.
Songs like “There’s Your Trouble,” “Wide Open Spaces,” and “I Can Love You Better” are all undeniable bangers! It’s no wonder that stars such as Taylor Swift absolutely adore them.
A controversial comment changed everything
But to say that The Chicks have a complicated history with country as a whole would be an understatement. Following heated statements about George W. Bush in 2003 when America invaded Iraq, the band was pretty much blacklisted.
Those within the genre turned their backs on them, and refused to recognize the success of the group’s 2006 record Taking the Long Way. Things got so bad that The Chicks didn’t make another album for close to 15 years. Think about where they could be in the pantheon of country legends if not for that controversy.
10. Alison Krauss
There are few bluegrass artists who have been able to touch Alison Krauss’ talent since she first emerged in the mid-1980s. She’s a very special musician, coupling her angelic voice with masterful fiddling skills.
It’s difficult not to be captivated by songs such as “When You Say Nothing at All,” “Ghost in This House,” and “The Lucky One.” They’re great demonstrations of just what Krauss is capable of.
More Grammys than Adele and Taylor Swift!
Mind you, Krauss isn’t exactly a mainstream name outside of country circles. That was made abundantly clear when Billboard ran an article in 2023 questioning who the “Queen of the Grammys” was.
The candidates were Adele, Taylor Swift, and Beyoncé. Now, barring Queen Bey, Krauss has won more Grammys than any other woman in history: she’s got 27 of them. It’s an astonishing number and her talent deserves wider recognition.
11. Dwight Yoakam
At a time when honky-tonk energy in country music was sadly lacking, Dwight Yoakam came along in the 1980s and changed all that. His sound was unique back then, intermittently dipping into both rock and punk.
It attracted keen followers of the two genres to country, which was a pretty impressive feat all on its own! “Guitars, Cadillacs” is an awesome starting point if, having read about him here for the first time, you feel that you want to dip into Yoakam’s back catalog.
Underrated in music and movies
Yet in the eyes of many people, Yoakam is still an underrated figure in the country music world. He’s not talked about in the same breath as some of the greats, despite his talent presenting a good case for it.
Meanwhile, he’s actually quite underrated as an actor, too. Yep, Yoakam has been in several Hollywood movies over the years, including Panic Room, Crank, Wedding Crashers, Logan Lucky, and Cry Macho.
12. Guy Clark
Often described as a “songwriter’s songwriter,” Guy Clark was certainly deserving of that label. His warm, poetic lyrics made him stand apart from most of his contemporaries. He also built a pretty big fan club along the way, one which included a name already on this list, Steve Earle.
Even Earle’s son Justin loved the guy, telling American Songwriter, “He’s like my Ernest Hemingway in a lot of ways. He taught me the beauty of simplicity.” Songs such as “Homegrown Tomatoes” and “Baton Rouge” are great examples of Clark’s lyrical brilliance.
“He’s so underrated”
Regardless of how well-liked Clark was in country-music circles, though, he didn’t achieve the same level of mainstream attention compared to his peers. The singer-songwriter wouldn’t have been out of place alongside Dylan or Woody Guthrie.
“He’s so underrated,” Nashville musician Drake White enthused to American Songwriter. “If you’re a writer and you don’t know about Guy Clark then, well...” He couldn’t even complete the sentence! Clark sadly passed away in May 2016.
13. The Del McCoury Band
A group that just oozes energy when they get going, the Del McCoury Band are a bluegrass powerhouse. Their on-stage synergy is off the charts! But when you consider the family connections within the band, that shouldn’t come as a huge surprise.
Del McCoury is the veteran frontman, while his sons Rob and Ronnie play the banjo and mandolin, respectively. Jason Carter and Mike Bub round things off on the fiddle and bass.
Surprisingly overlooked
Yet as great as they continue to be, The Del McCoury Band are often overlooked during chats about famed country music groups. The likes of Alabama, Brooks & Dunn, and Nitty Gritty Dirt Band all seemingly come up before them.
And that is quite surprising, considering Del and his boys actually did start to reach a mainstream audience in the 1990s. On top of that, they’ve won two Grammys, so the band hasn’t been without its success.
14. John Prine
From the very moment in 1971 that his first record hit the shelves, John Prine showed that he was a folk artist worth watching. The guy was a master at weaving humor into his music, as well as pointed political commentary.
“Your Flag Decal Won’t Get You Into Heaven Anymore,” “Some Humans Ain’t Human,” and “Dear Abby” are fine examples of that. Prine also wasn’t afraid to zone in on “historically specific” subjects in his songs.
“Narrow, specific style of execution”
As a result, Prine became a well-liked figure in folk and country circles. But he struggled to develop a similar connection with mainstream music audiences: none of his tracks really caught fire outside the genre.
As for why that was, in 2017 The Michigan Daily speculated, “[His] narrow, specific style of execution and the necessity of context may be a few of the reasons Prine is looked back on less frequently than some of his peers.” He passed away in 2020 at the age of 73.
15. Rosanne Cash
Following in the footsteps of her iconic father Johnny, Rosanne Cash had a lot to live up to when she entered the country scene. But she didn’t let performing in the shadow of his fearsome reputation overwhelm her.
Cash was able to carry on her family’s legacy thanks to her powerful voice and strong songwriting skills. Tracks such as “Seven Year Ache,” “If You Change Your Mind,” and “Blue Moon With Heartache” are real highlights from her back catalog.
An album ahead of its time?
Could Cash have been an even bigger name to music audiences at large, though? We’d say so. Her 1985 record Rhythm & Romance had all the qualities to smash through the proverbial glass ceiling. It was country with an MTV edge to it, infusing plenty of rock throughout the tracks.
Yet that unique sound seemingly worked against it, as the country albumonly just scraped into the top 40 best-sellers list for the year in Billboard. Ironically, if it had come out later, it might’ve been Cash’s ticket to wider mainstream acclaim.
16. Patty Loveless
Patty Loveless sat under the learning tree of Porter Wagoner and Dolly Parton before making her breakthrough in the 1980s. And boy, has she enjoyed an excellent career ever since.
Loveless boasts some of the purest vocals out there, combining country-rock with honky-tonk in her music. Her ballads are pretty special, too: “On the Verge of Tears” will doubtless have you reaching for a box of tissues!
Making her presence known
Loveless’ efforts haven’t gone unnoticed over the years. She’s a two-time Grammy winner and has made her presence known in the country charts. In fact, the musician racked up no fewer than five number one tracks between 1988 and 2003.
But despite all that, Loveless is still seen as a somewhat underrated artist in the genre. While there’s not much difference between them in terms of talent, she doesn’t have the mainstream name recognition of, say, Shania Twain.
17. Steve Earle & The Dukes
While we’ve already touched on Steve Earle, the same can’t be said for his excellent backing band. Known as The Dukes, they’ve done a great job showcasing the raw energy in his music across the years.
And the line-up has been flexible to say the least! The likes of Buddy Miller, Will Rigby, Norman Blake, Kelly Looney, and Eric Ambel have all been part of the group at some time or other. Even Earle’s sister and son joined the fun at times.
“Like being a Hells Angel”
In the grand scheme of things, though, like the singer himself, The Dukes have also gone under the radar of mainstream listeners. Yet Earle didn’t seem bothered by that as he hailed his colleagues during a chat with The Guardian in 2017.
He insisted, “I think everybody’s proud of being in this band. It’s like being a Hells Angel. We’re kinda badasses. It’s a really, really good band and the way we tour is hardcore — four shows in a row, then a night off at best.”
18. Old Crow Medicine Show
Old Crow Medicine Show made their bow in 1998 and didn’t waste any time in getting established. The band are big on embracing old country sounds, mainly using stringed instruments to create their toe-tapping tracks.
As Spectrum Culture put it, “The artists bring back old-timey music, but less as revivalists and more as forward-moving traditionalists.” The group has never been interested in mining nostalgia, either.
More than meets the eye?
So why hasn’t Old Crow Medicine Show found a broader audience beyond certain country music circles? Well, it might be down to the band’s overall presentation. At a glance, the music is fast and upbeat to an almost comical degree. You’d be forgiven for thinking there was little substance to it.
Yet that’s not the case: Paint This Town is a perfect example. That album has some really focused tracks on a variety of topics, from “Painkiller” to “New Mississippi Flag.” It proves the group can balance a sense of fun with lyrical seriousness.
19. Robert Earl Keen
Jumping between various tones and styles from song to song isn’t as easy as some musicians make it look. But for country star Robert Earl Keen, it really does seem to be an effortless switch.
“That Buckin’ Song” and “Corpus Christi Bay” are just a couple of examples from his back catalog showcasing that skill. The tone of the tracks couldn’t be more different! Keen is a tremendous singer-songwriter, infusing his music with plenty of acerbic wit.
Kept at arm’s length
Mind you, regardless of his undoubted talent, Keen still hasn’t been able to transcend genres to become a bigger star in the broader music industry. None of his songs or records have ever climbed to the top of the charts.
That’s not the only issue, though. Keen himself has always been a little reluctant to get too involved in the business, and that’s definitely played a role in the lack of widespread attention.
20. The Highwomen
Back in the 1980s country saw the formation of an exciting supergroup: the Highwaymen. The band’s star-studded members included Willie Nelson, Johnny Cash, Kris Kristofferson, and Waylon Jennings. It was like country’s version of The Avengers!
But then, several years later, a female take on that idea was born. And so, that led to the creation of the Highwomen, which features Natalie Hemby, Amanda Shires, Brandi Carlile, and Maren Morris.
An ambitious aim
The modern supergroup exists to help highlight the talent of women who’ve been overlooked and underrated in country in recent years. And while The Highwomen might lack the star-power of The Highwaymen, its members are determined to make a difference.
In 2019 Carlie told The New York Times, “It’s really important that the lack of representation for women in music doesn’t come across as some bougie, elitist problem. It’s regular people and regular little girls in small towns that don’t get access to their story being told.”