100 Greatest Country Artists of All Time

From architects of the genre like Hank Williams and Jimmie Rodgers to game-changers Garth Brooks and Shania Twain

Waylon Jennings
100
Waylon Jennings Clayton Call/Redferns7/100

7. Waylon Jennings

It's possible to sum up the entire Outlaw Country movement with just one letter: a flying W. The logo of Waylon Jennings, the stylized W is shorthand for one of the most popular subgenres of country music, founded primarily by an artist who, ironically, didn't want much to do with it. Listen to Jennings' "Don't You Think This Outlaw Bit's Done Got Out of Hand," cut in 1978 at the height of the craze, and you can hear the weariness in his voice. But Jennings couldn't help but be an outlaw; it was in his nature. The Texas native bucked Nashville convention by using his own backing band in the studio; favored an all-black aesthetic instead of gaudy rhinestones; and publicly fought with the Country Music Association, even having hats made up that read "CMA: Country My Ass." (His longtime drummer, Richie Albright, still wears his onstage today.)

Yet Jennings' contributions to country music go way past any ballyhooed rebellion. With a rich, growling voice and the twang of a leather-embossed Telecaster, Jennings helped create his own unmistakable sound, one that resonates today in the music of artists like Sturgill Simpson and Jennings' own son, Shooter. In 1973, he gave songwriter Billy Joe Shaver his big break by cutting nine of his songs on the LP Honky Tonk Heroes, including the signature title track and the brooding "Black Rose." To many, the album is regarded as Jennings' best, but Dreaming My Dreams, released two years later, paints a more complete portrait of the man. "Are You Sure Hank Done It This Way" is full of piss and vinegar; "Waymore's Blues" doubles as his own mantra; and "Dreaming My Dreams" is emotion laid bare, delivered by a guy who's man enough to admit he's had his heart broken. Jennings found a soul mate in 1969, marrying the singer Jessi Colter, and the pair recorded a series of duets. One of them, a spirited take on Elvis' "Suspicious Minds," ended up on Wanted! The Outlaws, the first country LP to sell one million copies. Jennings died in 2002 at 64 from complications of diabetes. J.H.

Key Tracks: "Are You Sure Hank Done It This Way," "Honky Tonk Heroes" 

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