Waylon Jennings evidently wasn’t a fan of Dwight Yoakam.
Waylon is a country music icon that ruled the outlaw music scene in 1970s, although he found country music success well before, and long after, that decade. Yoakam was one of the biggest stars in country music to come along in the 1980s and 1990s. The two stars overlapped a bit in the late 80s, but Jennings was never one to shy away from how he really felt, and certainly had some thoughts on the “new guy” who was coming into the genre and taking it by storm.
In this clip from 1988 that’s resurfaced, Jennings can be heard taking time out of his set to poke fun at Dwight Yoakam a bit – who had rather recently released his debut album Guitars, Cadillacs, Etc., Etc. at the time. Though everyone was going crazy for the new country act, Waylon wasn’t fully on board… telling people that Yoakam couldn’t sing, and that if they liked him, they had a bad taste in music:
“I haven’t figured this thing out. If you can’t sing, you can’t sing. And wiggling ain’t gonna help you none. Somebody oughta tell Dwight Joke-em that too. Oh you like Dwight? You’ve got your musical taste in your nose.”
If you are wondering that “wiggling” Waylon is referring to, Dwight Yoakam’s accustomed move was to do a little bit of a hip-swing movement as he played and performed in his tight jeans, especially in his younger career. For Waylon, a man who mostly stood in place and let the music do the talking, he didn’t like that. Of course, Dwight was always a bit “Hollywood” so to speak, but Wynonna Judd, who he dated briefly in the late ’80s, famously said he had a whole maneuver to squeeze into those tight pants.
But Waylon followed it up with an explanation, and it sounds like it was deeper than just singing:
“You know what, I’ve seen him treat people bad, that’s the only reason I said that.”
And to be fair to Waylon, Dwight has never had a reputation for being the nicest guy in the business. In fact, it’s long been speculated that Mary Chapin Carpenter’s CMA Awards performance of “The Jack*** I’m Opening For” was all about him, although she never confirmed it.
However, another country music legend, Johnny Cash, apparently didn’t care much for Dwight either, at least at that time. Jennings went on to tell a story to the audience of when Cash and Yoakam met for the first time. Even the “Man in Black” apparently said something to Dwight about his on-stage antics:
“I’ll tell you what, Johnny Cash got him better than anybody. And John would not hurt a fly, but he just doesn’t mince his words very much. Dwight came up to him and he says, ‘Hi there.’ He wanted to meet Johnny Cash. Johnny goes, ‘Well, Dwight, you remind me of myself about 30 years ago.’ Yoakam says, ‘What’s that?’ He goes, ‘You got that twitch down, now you gotta work on that singing.'”
Hilarious.
Although, Johnny would later go on to praise Dwight on a number of different occasions, telling Larry King that he was one of his favorites. He also reportedly said that Dwight was “the greatest voice in the history of country music,” shortly before his death.
Was Dwight Yoakam actually that bad at singing in his early career? No not necessarily… but was he known as a great vocalist? Probably not. The voice was certainly unique and interesting, but not exactly the strongest. Perhaps the older guys in the genre could feel the changing of the guard, and needed to pick out something that they didn’t like about the new artist.
Waylon ended his anti-Yoakam rant with this self-deprecating joke about himself:
“More power to Dwight. If it takes wiggling to get it, that’ll do it. You know I stumbled and staggered, that worked for me.”
@user1853283077211 Waylon on Dwight Yoakam. Kinda bizarre in my opinion. I love them both. #waylonjennings #countrymusic #concert #dwight #cantsing @Waylon Jennings ♬ original sound – waylonwilliamson
Ol’ Waylon was on one.
Since we’ve had so many different country music beefs in 2025, it’s nice to see that artists have been throwing jabs at each other for decades. That being said, I much prefer Waylon vs. Dwight over Zach Bryan vs. Gavin Adcock…
