We tip our hats to the country musicians who refuse to walk the straight and narrow.
Since the first generation of country music’s outlaws led by Waylon Jennings and Willie Nelson, the sound and the style defined by those artists have gone from sub-genre to cultural movement — one that’s trucking along a half-century later. To celebrate 50 years of going against the grain, we’ve gathered up a few of our favorite modern outlaws.
CHARLEY CROCKETT
The Texan descendant of Davy Crockett grew up in a trailer park, hopped freight trains, and even worked on a weed farm before his musical dream finally began to take hold. The “Welcome To Hard Times” crooner has gone on to drop acclaimed studio albums sell out shows worldwide, most recently landing a nomination for Best Bluegrass Album at the 67th Grammys for the LP $10 Cowboy.
JASON ISBELL
Jason Isbell first made a name for himself with the iconic Southern rock band The Drive-By Truckers before charting his own path with backing band The 400 Unit. The “Cover Me Up” singer has gone on to earn six Grammys in addition to becoming a crossover star with appearances on the animated television show Squidbillies and the Martin Scorsese drama Killers Of The Flower Moon.
CODY JINKS
Melding Texas country with Southern rock, Cody Jinks hit a hot streak in the 2010s with a string of four albums that hit high points on the country charts, beginning with 2016’s I’m Not The Devil. Songs such as “Hippies And Cowboys” and “Same Kind Of Crazy As Me” are odes to the ragtag creative class, while “Must Be The Whiskey” touches on the practice of using liquor to numb one’s pain.
JAMEY JOHNSON
A songwriter’s songwriter who has written tunes recorded by Willie Nelson, Merle Haggard, Trace Adkins, George Strait, and others, Jamey Johnson has also wowed listeners with his deep baritone stylings. “The Dollar,” “In Color,” and “High Cost Of Living” all cracked the top 40 on the country charts. In late 2024, Johnson dropped Midnight Gasoline, his first record in a dozen years.
MIRANDA LAMBERT
With the deliciously defiant 2005 major label debut, Kerosene, Miranda Lambert let the world know she wasn’t a songwriter—or a woman in general—to mess with. Nearly 20 years later, that remains the case with the “Crazy ExGirlfriend” hitmaker now regarded as one of the biggest movers and shakers in country music. Her groundbreaking tour productions and commitment to artistic excellence have inspired several artists in her orbit, from Caylee Hammack to Tenille Townes, Elle King, Maren Morris, and Ashley McBryde, all of whom she brought on her “Roadside Bars & Pink Guitars Tour” in 2019.
NIKKI LANE
Nikki Lane is as outlaw as they come. The South Carolina native dropped out of high school and began working as a fashion designer between New York City and Los Angeles before a bad breakup with a country singer led her to begin writing her own lovelorn tunes. Now she lives the best of both worlds, residing in Nashville while operating a vintage clothing store, High Class Hillbilly, and continuing to write, record, and tour.
POST MALONE
The Texas-raised artist (real name Austin Post) has shrugged off all misconceptions about himself with a pivot from hiphop-tinged pop music to traditional radio country on the star-studded album F-1 Trillion. Featuring Hank Williams Jr., Dolly Parton, Luke Combs, Morgan Wallen, and more, the project toes the line between present-day pop country and the 90s classics of Post’s childhood.
MARGO PRICE
Born in rural Illinois, Price has gone from being a Midwest Farmer’s Daughter to becoming a power player in the modern outlaw movement with songs like “Hurtin’ (On The Bottle)” and “Twinkle Twinkle.” Her work has garnered the praise of others known for going against the grain, such as Billy Strings, the late Loretta Lynn, Orville Peck, and Willie Nelson.
STURGILL SIMPSON
Whether it’s the twangy and psychedelic sentiment of Metamodern Sounds In Country Music, the soulful sounds of A Sailor’s Guide To Earth, or the raw brilliance of Cuttin’ Grass, Simpson has shown that it’s useless trying to put him in a genre box. If you do, he’ll just blow the whole thing up.
JAIME WYATT
If you were unsure of Jaime Wyatt’s outlaw status, just take a look at the title of her 2017 debut—Felony Blues. The autobiographical project centers around an eight-month stint she served in the LA County jail for robbing her heroin dealer. The heartache and redemption come through in songs such as “Stone Hotel.” The queer country singer eventually dove into the catalogs of Merle Haggard, David Allan Coe, and Johnny Cash, influences at the forefront of her two albums that followed—2020’s Neon Cross and 2023’s Feel Good.
From our February/March 2025 issue.
PHOTOGRAPHY: (Lead image) Lyza Renee
