Country Throwback: Watch Waylon Jennings Sing ‘Waymore’s Blues’ to Wife on TV

by Chris Haney

In this edition of our Country Throwback series, we’re revisiting outlaw country legend Waylon Jennings singing “Waymore’s Blues” to his wife.

Back in 1974, Jennings and his musician wife Jessi Colter joined Cowboy Jack Clement’s television show. The outlaw country power couple married in 1969 and stayed together until Jennings passed away in 2002. In addition, the couple often worked together, including their popular Wanted! The Outlaws compilation album with Willie Nelson and Tompall Glaser.

During their TV appearance, the couple’s chemistry was on full display as Jennings sang to his wife and they joked around together. Jennings chose to play one of his more amusing tracks on the show when he sang “Waymore’s Blues.” Clements can be heard in the background joking that he’s never heard of the song. In fact, he produced 1974’s Dreaming My Dreams, the album that features the track.

Jennings sings the song alone as he casually strums his beautiful acoustic guitar. As he gets to the third verse of the song, he sings “What makes me want to love every woman I see? I was trifling when I met her now I’m trifling again.” He smiles at his wife and chuckles before saying “poetic license” to her.

“Oh? You’ll need a lot of poetic license for that,” Colter hilariously responds.

Waylon Jennings Amusingly Says the Song Doesn’t Make Any Sense

As Waylon Jennings is finishing up the song, he tells Jessi Colter that the first part of the song is about early country icon Jimmie Rodgers. He then claimed that he sang “Waymore’s Blues” as a joke to author and songwriter Shel Silverstein and said the song doesn’t make any sense.

“Is that right?” a bemused Colter asked. “It’s truth!” Jennings responded earnestly.

“You didn’t think it made any sense when you wrote it?” she playfully asked.

“It don’t make any sense. It does, but it don’t. I had to really dig to get a story out of it,” he said with a laugh.

“Honey that’s not the way you do it. You don’t say that it has a concept after you’ve finished it,” Colter joked with her husband.

Jennings takes a hit of his cigarette and says, “It was a good song, alright?”

It’s not hard to see why the couple made it so long. Their connection and witty banter was evident even in the short clip.