The 10 Best Country Outlaws

LxL_TopTenThursdays_02_900x300Best Country Outlaws

The rogue western figure has been making its way back into pop culture recently, not only with musicians like country artists like Jamey Johnson and Kacey Musgraves, but also in television and movies, most notably with the Elmore Leonard (RIP) adapted FX series Justified. Between Justified’s season finale Tuesday night and the Archer season surrounding Cherlene turning into an outlaw country star (“OUTLAW COUNTRY!”), here are our 10 favorite country outlaws.

10. Merle Haggard

Merle Haggard - Outlaw Country

Haggard was part of the old guard of outlaw country musicians, and while many of his peers were singing sweet songs about the country life, Merle was living a more rock ‘n’ roll lifestyle and stepping out musically. His 1969 hit “Okie from Muscogee” has become an outlaw country anthem of sorts, showing pride in his country roots but still remaining a rebel at heart.

9. Jason Isbell

Jason Isbell - Outlaw Country

Leaving southern rockers Drive-By Truckers behind in 2007, Alabama’s Jason Isbell has become one of the most promising young songwriters, and while he has sobered and married up, Isbell still has an renegade spirit to his music.

8. Waylon Jennings

Waylon Jennings - Outlaw Country

Waylon Jennings is the first of the four members of the Highwaymen (Waylon Jennings, Kris Kristofferson, Willie Nelson, and Johnny Cash), the outlaw country equivalent of the Traveling Wilburys, to make this list. Jennings in the 70’s embodied outlaw country, by refusing to fit the polished sounds of Nashville and instead making a rougher update of honky tonk.

7. David Allan Coe

David Allan Coe - Outlaw Country

I was unfamiliar with Coe when we made this list, but Austin pushed hard for Coe and I can see why. Coe is a big personality vocally, sung about getting in trouble and being on the run, and lived a true renegade lifestyle synonymous with outlaw country.

6. Steve Earle

Steve Earle - Outlaw Country

Being propped up by his roles in David Simon’s The Wire and Treme, Earle has gained a second life musically by gathering a new generation of fans. Rebellious yet earnest, Steve Earle lands at the crossroads of outlaw country and heartland rock, thanks to his love to another outlaw on our list, Townes Van Zandt.

5. Willie Nelson

Willie Nelson - Outlaw Country

Really known as the face of outlaw country, Willie got penalized on this list for his work with Toby Keith, and we have a strict saying for anything related to Toby Keith: “No thank you.”

4. Kris Kristofferson

Kris Kristofferson - Outlaw Country

Probably the most underrated of the Highwaymen, Kris Kristofferson had a way with words and telling interesting and intelligent stories.

3. Lucinda Williams

Lucinda Williams - Outlaw Country

The smoky-voiced Lucinda Williams can also write a song with the best of them, but she is also has sort of a biker-chick edge to her. Her 1998 album Car Wheels On a Gravel Road is an absolute gem and good starting point for Lucinda’s music, if you aren’t familiar with it.

2. Townes Van Zandt

Townes Van Zandt - Outlaw Country

Sort of the Velvet Underground of country, Townes is every country musician’s favorite musician, and with good reason. While he never reached the commercial success of many of his peers, he has left beyond a greater legacy of timeless songs than maybe any other country musician. “If I Needed You”, “Pancho and Lefty”, and “To Live is to Fly” are just a few of the legendary songs he left behind after he tragically died in 1997 due to a heart attack related to addiction.

1. Johnny Cash

Johnny Cash - Outlaw Country

We just came off a bit of a Johnny Cash week in March with the release of his surprisingly good lost-80’s album Out Among the Stars and our Top Ten Johnny Cash songs list, Johnny Cash was truly an outlaw at heart and had the brilliant tunes to match it, making him the obvious choice for number one on this list.

Todd – Todd Snider

Todd Snider - Outlaw Country

Maybe the most borderline outlaw country artist on this list since he isn’t too country, Snider is still truly a rebel at heart, and his songs are country at heart even if they don’t sound the part.

Wes – Drive-By Truckers

drive-by truckers - Outlaw Country

We all love Jason Isbell, but I was surprisingly the only one in the group pushing for Drive-By Truckers. Sure they are southern rock, but  they are still rebels at heart, and write a song as well as they can wield a bottle of whiskey.

Austin – Jamey Johnson

Jamey Johnson - Outlaw Country

The shaggy Nashville artist Jamey Johnson has reignited the spirit of dark spirit of the early country outlaws, and has gotten plenty of acclaim for it.

Author: Wes

Hoosier. Writer. Music Buff. Media Man. Tourist. Polar Bear.

3 thoughts on “The 10 Best Country Outlaws”

    1. We didn’t feel like senior fit the ball, and we either aren’t as big of fans or don’t know Jr and III’s music as well, so that’s why those missed the cut.

  1. How could Hank Sr. not fit the ball? He wrote the playbook? Getting kicked off the Grand Ole Opry because he refused to conform to the strict Opry policies, and for getting drunk too often and missing too many shows. Not only was he the epitome of the country outlaw, he was a rock star before their was such a thing, and his death still shakes the heart of country and the soul of rock and roll. And if getting drunk, getting into fights, missing shows, and dying young from a lethal combination of drugs and alcohol isn’t enough, the man wrote an incredible amount of songs at a level that only Dylan, Haggard, Guthrie, or Jimmie Rodgers could rival. And that music speaks to the outlaw in everyone on this list. Heartbreak, cheating, wandering down life’s lost highway; he’s the king of the country outlaw. So much the country outlaw that Nashville and Chet Atkins spent the next 50 years trying to put strings on everything to distance itself from the very hillbilly rebel sound that Hank unleashed and that country music fans first fell in love with. And it’s that sound that everyone on this list channeled in their own music careers. But, if Hank is too old timey for you, his grandson Hank III keeps his Grand Dad’s spirit alive on a whole new hellbilly level. I suppose it’s fine to put David Allan Coe on the list. The man did do some time in prison, wrote some bad ass songs, wrote some racist songs, and I guess that makes him a country outlaw, but all you need to see is his frilly outfit in the incredible video Heartworn Highways to question his place on the list. IMHO

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