(AP Photo/John Russell, File)

Next week, two of country music’s die-hard iconoclasts hitch their wagons here in Winnipeg.

On Sunday, roots goddess Lucinda Williams brings her tales of ravaged romance to the Burt, and on Wednesday, red-headed rebel Willie Nelson lights up MTS Centre for the second time in as many years.

But Nelson and Williams have more than tour schedules in common. They’re part of the same musical kin — one characterized by anti-authoritarian attitudes and a willingness to explore new terrain.

We like to think of them as country bad-asses — good ol’ innovators whose refusal to play by Nashville’s rules places them in league with their rock ’n’ roll contemporaries.

Here’s a list of our 10 faves:

1) Hank Williams: With an aversion to lyrical bull and a voice that could fell a tree, Williams found favour with both the well-heeled Opry crowd and the honky-tonk rowdies. Hank’s life story was rife with the elements of a good country song — namely, endless troubles with booze and women, plus one too many lonely nights on the road. And while they ended up killing him, those vices also leant his songs a haunting everyman quality that every country singer worth his salt has drawn inspiration from in the ensuing decades.

2) Johnny Cash: No list of bad-asses would be complete without the Man In Black, whose rebel mythology has been romanticized to the point that people still confuse the singer with his songs. Yes, Cash was hopelessly hooked on booze and pills (until June helped him find religion, anyway), and yes, he spent time in prison (a matter of hours, according to most accounts). But no matter how convincing the performances sound, he never beat the tar out of his father for saddling him with a girl’s name, and he never shot a man in Reno just to watch the poor sap die.

3) Willie Nelson: Where to begin? Lots of people love Willie for showing such solidarity with the marijuana crowd (and for getting away with it as long as he has). Just as many love him for his working-class heroics, which saw him sticking with the Farm Aid fundraisers he helped launch even after the IRS billed him for $17 million in back taxes. But for our money, it’s Nelson’s devil-may-care approach to music that makes him one for the ages. How many other hillbillies do you know who could get away with a CD of reggae classics AND an ode to gay cowboy lovin’, all in the same year?

4) Merle Haggard: Like many on this list, The Hag is well acquainted with the inside of a jail cell, having spent three years in San Quentin for a 1957 robbery (not to mention being shuffled through countless detention centres as a teen). In fact, it was at one of Cash’s famed concerts from inside San Quentin’s walls that Haggard was first inspired to trade in his ill-gotten gains for a guitar, kick-starting a lengthy career as one of the pioneers of the outlaw country movement, and as the most unapologetic Okie ever to hail from Muskogee.

5) Loretta Lynn: Proving that “bad-ass” is not the exclusive domain of the boys, Lynn overcame a hardscrabble existence to become one of country’s brightest lights. Think of her as the tough-living yang to Dolly Parton’s fresh-scrubbed yin: while Dolly was beggin’ Jolene not to steal her man, Loretta just spelled out — in no uncertain terms — the harm that would come to any woman who crossed her. And even though Dolly got the cover treatment by the White Stripes, it was Loretta with whom Jack White chose to record an album.

6) Steve Earle: Another former jailbird, Earle’s promising career as Nashville’s Bruce Springsteen stalled in the ’90s when his heroin addiction spiralled out of control. But it’s his post-prison achievements that set him apart. Whether raging against the death penalty, drumming up votes for John Kerry, or writing a song from the perspective of American Taliban John Walker Lindh, Earle continues to prove that even with a checkered past, you can still mount a credible challenge to the status quo.

7) David Allen Coe: With his twisted humour and lyrical boasts, Coe has always made as many friends as enemies. He was accused of racism after dropping n-bombs in the ‘70s, and has neither confirmed nor denied he spent time on Death Row for killing a fellow convict. The racism charges are probably bunk (some of Coe’s best friends in the clink were black, including cellmate Screamin’ Jay Hawkins). Plus, he comes recommended by no less a bad-ass than Pantera axeman Dimebag Darrell, who was collaborating with Coe when he was gunned down by a crazed fan in 2005.

8) Waylon Jennings: Jennings famously bailed on the plane trip that killed Buddy Holly, Ritchie Valens and Big Bopper, but it’s his stint as an outlaw icon in the ’70s that really gave him new life. Though he struggled with cocaine addiction and financial debts, he managed to get both under control, citing his son Shooter (himself an outlaw up-and-comer) as the inspiration. And if that’s not enough, he also recorded the theme song to the Dukes of Hazzard — the very definition of bad-ass to those of us raised on trash TV.

9) Gram Parsons: As a member of The Byrds and Flying Burrito Brothers, Parsons helped usher in the country-rock movement of the 1970s (and the alt-country boom of the ’90s). He didn’t get to reap the spoils of either, fatally ODing in ’73 at the tender age of 26. But while alive, he spurred The Rolling Stones to explore their inner cowboys, introduced earth angel Emmylou Harris to the world stage, and floated the term “cosmic American music” for the first time. Not too shabby for a guy in a psychedelic Nudie suit.

10) Lucinda Williams: For a while, Williams was known better for her songwriting than her singing, winning a Grammy for 1992’s Passionate Kisses only after it was covered by Mary Chapin Carpenter two years later. She found mainstream success with 1998’s Car Wheels on a Gravel Road, but had trouble repeating the feat with either of its followups. These days, the notorious perfectionist — who flips seamlessly from strong-willed feminist to wounded lover in her songs — may have stumbled upon her most challenging role yet: She’s engaged to be married.