The best thing about Waylon Jennings is his music, without a doubt. However, there’s also something to be said about the famed outlaw country singer’s personality and attitude. He had quite a few disruptive but low-key hilarious moments through the years, and we’re going to celebrate a few of them on this list. Let’s take a look at five times Waylon Jennings made it clear that he couldn’t care less!
1. When He Walked Off Tom Synder’s Show
You’re going to notice a pattern on this list. Waylon Jennings was the kind of man who had no qualms with leaving a place if he didn’t want to be there. It’s inspiring, really.
In 1998, Jennings was slated to appear on The Late Late Show with Tom Snyder. Ahead of his appearance, Jennings was allegedly already PO’d about not getting a full-hour slot on the show. The producers opted to have him share his slot with Dr. Laura. Matters got worse when Dr. Laura’s segment started to go over time. Jennings was sick of it, got in an elevator, and straight-up left the studio.
2. When He Walked Out on a Contract Negotiation
This debacle is known as the “$25,000 P*ss” incident. In 1972, Jennings was fighting for control of his own music. He ended up hiring a lawyer from New York to help him renegotiate his contract with RCA, as that very lawyer helped his pal Willie Nelson do the same thing.
The label refused to give Jennings a lump sum of $25,000. All of the involved parties were basically waiting in a room for one party to budge. Jennings was sick of it and went to go use the bathroom, without saying a word. Before he returned, the label reps panicked in his absence and agreed to give him the money. Allegedly, his lawyer said, “That was a $25,000 p*ss. You’re a f***in’ genius.”
3. When He Walked Out of “We Are The World” Recording Sessions
Jennings was one of many famous musicians to contribute to Michael Jackson and USA For Africa’s super-collab “We Are The World” in 1985. Surprisingly, Jennings didn’t make the cut. He walked out of the studio before they even finished the recording session.
Allegedly, Jennings didn’t want to attempt to sing in Swahili. Context is important here: This was very much not a racially motivated walk-out. Jennings didn’t want to record so late in the evening, he was old and tired, and a number of other musicians thought that singing in Swahili could be seen as the group “mocking” the ethnic groups they were trying to help with the charitable song. Despite leaving, Jennings is still credited on the release.
4. When He Started up a Motorcycle in a Hotel Room at Midnight
As a birthday surprise for Jennings in 1979, Joe B. Mauldin found a lovely vintage 1958 Ariel Cyclone motorcycle that once famously belonged to Buddy Holly. He parked it in the singer’s hotel room for him to find.
It was a sweet gesture. However, hotel staff (and guests) weren’t particularly happy when Jennings swung his leg over the bike and launched the particularly loud kickstarter. Did we mention he did this at midnight?
“It sounded twice as loud bouncing off the walls of that hotel room,” Jennings said. “I knew Buddy [Holly] wouldn’t mind.”
5. When He Sang a Cute Diet With Big Bird on Sesame Street
Waylon Jennings couldn’t care less about a lot of things, but he did have a soft spot for the kids. This adorable Jennings moment proved that the outlaw country singer had a tender spot, at least sometimes. Real outlaws know how to get in touch with their sensitive side.
Years ago, Jennings appeared on Sesame Street to sing a sweet rendition of “Ain’t No Road Too Long” with Big Bird. It’s a rare glimpse into the softer side of the “Good Hearted Woman” hitmaker.
Photo by Michael Ochs Archives
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