Still Roaming Heartworn Highways: As CUFF celebrates the old guard with classic doc, Keri Rak introduces you to country music’s most notable new-school outlaws

In the 1970s, the term “Outlaw Country” would define successful artists like Willie Nelson and Waylon Jennings, who rejected the Nashville music machine in order to work with producers of their choosing and take a new musical direction. 

In 1976, the million plus-selling compilation album Wanted! The Outlaws featuring Waylon and Willie along with Sammi Smith and Tompall Glaser would cement the subgenre and give musicians a marketable outlet for country that wasn’t the polished, heavily produced Nashville sound – but one focused on songwriting, stories and attitude. 

Still, while success often meant critical acclaim, it didn’t always translate to radio play, and, as a result, outlaw country is a term given but not taken (listener beware: if artists describe themselves as outlaws, they usually aren’t). 

Johnny Cash and Kris Kristofferson would take this route, while other Nashville outsiders like Billy Joe Shaver, Townes Van Zandt, Guy Clark, Tanya Tucker and Steve Earle would also pave the way for a next generation of outlaws to succeed without mainstream industry or radio support. (Ed.: You can get an exceptional primer on that with director James Szalapski’s brilliant 1976 documentary Heartworn Highways, which CUFF is screening as part of this year’s online festival running April 23 to May 2.)

Out of the current crop of new-school outlaws you should check out, here are 10

  1. Waylon Payne: Named after the other Waylon, he’s the son of Sammi Smith and longtime Willie Nelson guitarist Jody Payne. The songwriting chops follow the bloodline. (Also see other outlaw offspring: Lukas Nelson & Promise of the Real, Shooter Jennings, Justin Townes Earle).
    Listen: Blue Eyes, The Harlot, The Queer, The Pusher & Me
  2. Sturgill Simpson: He’s made a name for himself as country’s No. 1 outsider and overall most crusty personality. Since 2016’s Album-of-the-Year-nominated A Sailor’s Guide to Earth, he’s put out a soundtrack to a Japanese anime film (Sound & Fury) and two volumes of bluegrass covers of his own songs. He’s never boring.
    Listen: Cuttin’ Grass Vols. 1 & 2
  3. Mickey Guyton: Gave up on Nashville to focus on writing songs that spoke to her own lived experience and this year became the first Black female ever nominated for a country music Grammy.
    Listen: Bridges EP
  4. Jaime Wyatt: Like many of these outlaws, used a difficult past full of loss, heartache and addiction to fuel brilliant songs that are at once personal yet speak to so many. Her most recent record is produced by Shooter Jennings and features his mom, outlaw royalty Jessi Colter.
    Listen: Neon Cross
  5. Orville Peck: It doesn’t get much more outlaw than being a queer, mask-wearing Canadian. The songwriting is top-notch and the voice is like butter. Shania Twain even came out of retirement to guest-star on his most recent EP.
    Listen: Show Pony EP
  6. Margo Price: Accepted by Nashville legends like Loretta Lynn (she’s on Loretta’s latest album), yet called out by mainstreamers for talking too much politics (such as her vocal support of the BLM movement). Go ahead – tell her to shut up and sing. I dare you.  Listen: All American Made
  7. The Highwomen: Taking the camaraderie of Waylon, Willie, Kris and Johnny into a new, more inclusive era. Each woman on her own is a force: Brandi Carlile, Amanda Shires, Natalie Hemby and Maren Morris. Together, they’re even better. They famously hang with other cool outlaws like Amanda’s husband, Jason Isbell, Sheryl Crow, Yola and Dolly Parton (OK, fine, Dolly’s never been considered an outlaw really, but she is cool).
    Listen: The Highwomen
  8. Corb Lund: Alberta’s own legit cowboy with punk rock/grunge roots, his songs tell authentic stories in the best country tradition. In his free time, he stands up for Alberta’s land and water in the midst of government coal policy changes. Outlaw!
    Listen: Agricultural Tragic
  9. Nikki Lane: With a retro look and a sound that’s somewhere down the line from Tanya Tucker and Nancy Sinatra, Nikki Lane oozes cool. Whether she’s on her own or working with Black Keys’ Dan Auerbach, Queens of the Stone Age’s Josh Homme, or singing with Lana Del Rey, she’s following her own map.
    Listen: Highway Queen
  10. Queen Esther: She calls her sound “Black Americana,” and the New Yorker’s latest features original songs as well as covers of George Jones, Sister Rosetta Tharpe and even The Eagles.
    Listen: Gild the Black Lily (released March 26th)

Keri Rak co-hosts CJSW’s country music program, Tombstone After Dark, on Tuesday nights from 7 to 8 p.m. MST and also hosts a mixed-genre program called The Wake-up Shake-up on CKUA every Saturday morning from 8 to 10 a.m. MST.