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List of Outlaw Country Country Singers

The Grizzly Rose has long been a hub of country music in Denver for decades, and many of the outlaw country greats have played within its walls. Waylon Jennings and Willie Nelson are just some of the outlaw pioneers that have serenaded Denver with their unique sounds throughout the years. Check out our list of the top outlaw country singers past and present, and learn how this rebellious subgenre of country came about.

List of Best Outlaw Country Artists

What is Outlaw Country?

Outlaw country is an important part of country music history, first pioneered by several artists in the 1970’s. Although the exact origin of outlaw country is credited to different artists, there’s a common theme: the outlaw country artists wanted the freedom to write, perform and record their music their way.

Outlaw country began in response to the “Nashville Sound”, a formulaic style of mainstream country music being produced in Nashville at the time. When rock ‘n’ roll rose to prominence in the 50’s, country music sales began to falter. RCA Victor manager Chet Atkins, music producer Steve Sholes, Owen Bradley, Bob Ferguson and Recording Engineer Bill Porter then created the “Nashville Sound” by replacing honky tonk instruments like fiddles, steel guitar and nasally vocals with smooth string sections, background vocals and crooning from 1950’s pop. Country began to take on a slick production and notable pop music structures using the same studio musicians and vocal backing crews.

The “Nashville Sound” may have saved country music, but it created a powerful counterculture to country music in the process.

Negotiating For Freedom

In the 70’s a host of country stars negotiated contracts with RCA and other major labels to be able to write and produce their own albums- in other words, musical freedom. Breaking away from the mainstream and taking the reins on complete creative control made these artists- big names like Bobby Bare, Willie Nelson and Waylon Jennings – outlaw country singers.

Mainstream Nashville was dismissed by outlaw country artists, who instead preferred playing smaller, more honky-tonk style venues in Lubbock and Austin, Texas. In addition, the sound of Southern Rock from Muscle Shoals, Alabama was also having a profound impact on outlaw country.

Within no time at all, the world-weary, satirical and introspective lyrics of outlaw country became an important movement in country music history. That movement is still celebrated today!

Nashville Outlaw Country

Famous Outlaw Country Singers


Waylon Jennings

This famous Texan was discovered by Buddy Holly, and roomed with Johnny Cash in Nashville. Jennings bucked the RCA studio system, and despite being frozen out of the music mainstream for a few years, waged a successful battle against the mainstream music industry, recording some of his best material in these years.

Merle Haggard

This bad boy from Bakersfield was known as the “poet of the common man.” A rebel in his youth, he channeled his energy and musical talent into defining the honky-tonk sounds coming out of Bakersfield that were nothing like the smooth “Nashville Sound” at the time. Merle was also famously reluctant to discuss his past being in and out of prison, until Johnny Cash encouraged him to talk about it so that the tabloids wouldn’t be able to. Because of Cashes sage advice, we have legendary Haggard hits like “Mama Tried” and “Sing Me Back Home” today.

Johnny Cash

No list of outlaw country singers would be complete without “The Man in Black.” Johnny Cash was born and raised in Arkansas, and began pursuing his musical passion in earnest when he was stationed in Landsberg, Germany with the Air Force and formed a band – “The Landsberg Barbarians.” He went on to record for Sam Elliott at Sun Records, and topped the charts for multiple decades. In fact, he became the youngest living inductee in the Country Music Hall of Fame in 1980, at the age of 48. He was also inducted into the Rock and Roll Hall of Fame in 1995.

Outlaws tend to stick together. Johnny Cash also famously formed a supergroup with Willie Nelson, Waylon Jennings and Kris Kristofferson in 1985. The group, dubbed “The Highwaymen” released three albums within the next 10 years.

Willie Nelson Outlaw Country

Willie Nelson

A true veteran of country music, Willie Nelson’s musical career has seen many incarnations over his lifetime, and it’s not done yet. No stranger to dance halls and honky tonks, Willie was playing guitar and singing for money since the age of 13. Though he traveled to Nashville to play music, he found mixed results there. However, some of his songs became chart-topping hits for other performers, like “Crazy.” Patsy Cline’s version of the tune became the most played jukebox hit of all time.

Nelson’s pursuit of finding his own unique sound and embracing outlaw country brought him new success in Austin, Texas at the heart of the hippie music scene. The Armadillo World Headquarters became one of his favorite places to perform his unique blend of country, jazz and folk. Noted for his close friendships and frequent collaborations with Johnny Cash, Merle Haggard and Waylon Jennings, Nelson helped pave the way for modern outlaw country artists, including the next gentleman on our list.

Chris Stapleton

Chris Stapleton has been dubbed “the savior of country music” by some, and his style is up for fierce debate by traditionalists. Even Alan Jackson had words on the topic, as he doesn’t consider Chris Stapleton country!

What he’s making now really isn’t real country: It’s more like bluesy, Southern rock kinda stuff. I love it, it’s great, but he’s the closest thing to country out there.” –Alan Jackson

However, that’s precisely what makes Chris Stapleton the poster boy for modern outlaw country. Just like the greats that came before him, from Jennings to Nelson and beyond, Chris incorporates bluegrass roots, rock, country and blues into a unique tenor sound that is both relatable to the masses, while highly individual. In addition to a highly successful solo career, Chris has written chart-topping hits for mainstream country music greats, including Luke Bryan’s “Drink a Beer” and George Straits’ “Love is Gonna Make It Alright.”