Waylon Jennings Once Said Garth Brooks Was the Most Insincere Person He Ever Saw

Sometimes you need an old outlaw to call out what everyone else is too polite to say out loud.

Back when Nashville was shape-shifting in the ’80s and ’90s, country music was busy swapping grit for gloss, and nobody felt that tension harder than Waylon Jennings. Waylon, the man who made Outlaw Country an actual thing, had zero time for the polish and pop hooks rolling in behind guys like Garth Brooks. And to hear him tell it, Garth wasn’t just the poster boy for a softer, shinier sound — he was the embodiment of everything fake about it.

In a 1994 chat with The Inquirer, Waylon didn’t bother sugarcoating his feelings. “I think he’s the luckiest s.o.b in the world. He’s gotten more out of nothing than anybody I can think of,” he said. That’s about as Waylon as it gets. A punch line in a barroom brawl that never really ended. But it didn’t stop there. According to Bruce Feiler’s Dreaming Out Loud, Waylon doubled down with a line that still hits like a cheap shot all these years later: “He’s the most insincere person I’ve ever seen. He thinks it’s going to last forever. He’s wrong.”

You can almost picture Waylon leaning back in his chair, cowboy hat tipped low, letting that word “insincere” hang in the air like smoke from a Marlboro. This wasn’t just about music. To Waylon, Garth’s whole vibe rubbed him raw. Here was this hat-act kid, flashing a toothy grin and hugging every fan within reach, and it just didn’t track for a man who’d fought tooth and nail to keep Nashville’s bigwigs out of his music.

Meanwhile, Garth? He never really fired back. The closest he came to biting back was a shrug and a “Yeah, I was definitely the guy he targeted.” Brooks kept it classy when Broadwayonair asked him about the feud. “The guy’s a legend and deserves nothing but respect.” You can almost hear Waylon barking out a laugh if he were alive to read that now. Garth’s the kind of guy who’d say please and thank you after taking a punch, and maybe that’s exactly what drove Waylon nuts.

To be fair, Garth wasn’t just playing by different rules. He was rewriting the whole damn rulebook. He gave country a stadium-sized makeover, brought pyro and headset mics into the honky-tonk, and sold records by the millions. While Waylon’s songs howled about hard roads and rebellion, Garth was busy singing anthems that even soccer moms could blast with the kids in the backseat. For the Outlaw generation, that was the beginning of the end.

But here’s where it gets wild. All these years later, Garth’s “bubblegum” country now sounds downright classic compared to the genre’s pop-rap experiment of the last decade. That’s the irony. The guy Waylon called “the most insincere person” is now the traditionalist in a scene that’d make both of ’em spit out their whiskey.

The clash between these two legends wasn’t just an old man griping about the new kid. It was a line drawn in the dirt about what country music should stand for. Raw versus polished. Rebel versus sweetheart. Truth versus showmanship. And if you think about it, that battle’s still raging today every time someone flips on the radio and says, “This ain’t country.”

Waylon might’ve taken that disdain to his grave, but even he’d probably admit one thing. Garth didn’t go anywhere. He’s still out there packing stadiums, grinning ear-to-ear, giving the people what they want. Sincerity or not. Maybe that’s what stings the most. Because in the end, there’s room in country music for both kinds: the gun-slinging outlaws and the grinning megastars. And the feud between these two proves it’s a fight that keeps country alive.

Tip your hat to Waylon for saying what was on his mind. And tip your hat to Garth for surviving it, smiling all the way to the Hall of Fame.