They don’t call them outlaws for nothing. While recording his 1978 album I’ve Always Been Crazy, Waylon Jennings requested a pound of c*****e be flown into his from New York City and delivered to the studio in Nashville, Tennessee. The “order” led to Jennings’ arrest by federal agents for conspiracy and possession of the drug and inspired his song “Don’t You Think This Outlaw Bit’s Done Got Out of Hand,” which peaked at No. 5 on the Billboard Hot Country Singles chart.
A pioneer of outlaw country, when it came to his music Jennings continued doing what he wanted from the beginning of his career through the end, until his death in 2002 at 64. His antics often resulted in him walking out of the situation that didn’t suit him. Here’s a look at five moments when Jennings up and left a performance, recording, or business dealing.
[RELATED: Waylon Jennings Starred on ‘Married… With Children’ and Had a Chance Encounter with ‘Al Bundy’ Years Earlier]
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1. Leaving the CMA Awards (1970)
When Jennings’ performance time was cut at the last minute during the Country Music Association (CMA) Awards at the Grand Ole Opry on October 14, 1970, he left the building. “It was Kris Kristofferson’s night,” remembered Jennings. “He was a shoo-in for several categories.” That night, Kristofferson picked up the Song of the Year award for “Sunday Morning Coming Down,” which became a No. 1 hit for Johnny Cash.
That evening, Jennings was scheduled to perform his 1968 hit “Only Daddy That’ll Walk The Line,” but was asked to cut the song to one verse and chorus. “I said, ‘Why don’t I just dance across the stage and grin?’” said Jennings. “‘Maybe do one line. That’ll give you a lot of time.’”
Jennings added, “They told me to not get smart. Either I did it or I got out. They said, ‘We don’t need you.’ I decided that was true, and I left.”
Years later, Jennings returned to the CMAs and picked up a Best Male Vocalist award for “I’m A Ramblin’ Man” in 1975. Jennings was also nominated for Song of the Year for “I’m a Ramblin’ Man,” Album of the Year, and Entertainer of the Year.
2. The Bathroom Break That Earned Jennings $25,000 (1972)
In 1965 Chet Atkins signed Jennings to RCA Victor. A year later, the outlaw finally made his way onto the Billboard Hot Country Songs chart (at No. 49) with “That’s the Chance I’ll Have to Take.” By 1972, Jennings wanted more control of his music under the label and hired lawyer Neil Reshen—who previously helped Willie Nelson break from his contract with RCA—to help him renegotiate his contract with Atkins.
In his 1996 memoir Waylon: An Autobiography, Jennings recalled his contract dispute with RCA when he initially asked the label for a $25,000 advance on his royalties and was offered $5,000, under the condition that he sign with them for another five years.
“It was down to a $25,000 sum, and they were not going to give it to me,” remembered Jennings. “We were sitting there, not a word spoken, and the silence got unbearable. After a while, I couldn’t take it anymore. ‘Chet,’ I said, reaching over to a bowl on his desk, ‘where’d you get these peanuts?’ Neil glared at me. ‘Shut up, Waylon.’
Jennings continued, “You could hear a clock tick in the room. It got even quieter. Minutes had passed. I rose up, never said a word, [and] walked out. I went to the bathroom to take a leak. When I came back, Neil greeted me in the hall. ‘You’re a f–kin’ genius,’ he said.”
Jennings was confused at first until Reshen explained the situation to him. “Walking out like that, that sewed it up,” said Reshen, according to Jennings. “That was a $25,000 piss. [Reshen said] ‘They asked me where you went and I told them I didn’t know. Waylon’s mad, I’m sure. He’s crazy. He’s liable to do anything. … I guess he’s gone, so we may as well call this to a close.’ And that when they gave us the money.”
3. Waylon Refused to Sing Swahili on “We Are the World” (1985)
Even though his fellow Highwayman Willie Nelson and Kenny Rodgers appeared on the 1985 USA for Africa charitable hit “We Are the World,” Jennings walked out during its recording. The session started late at night following the American Music Awards and when Stevie Wonder suggested adding some lyrics in Swahili—sha-lum sha-lin-gay—Jennings knew it was time to leave. A photographer reportedly heard Jennings say, “Well, ain’t no good ol’ boy ever sung in Swahili. I think I’m outta here.”
In The Greatest Night in Pop documentary from 2024, Lionel Richie, who co-wrote “We Are the World” with Michael Jackson later recalled: “Waylon walks out of the door. [He was like] ‘I’m not dealing with this. I don’t know what that means, but I am not gonna say it.’ And we lost Waylon right there.”
Wonder had two Ethiopian singers in the studio but later learned that Ethiopians don’t speak Swahili before abandoning the idea. Several artists, including Ray Charles, were also against the idea of adding another language. “It’s three o’clock in the goddamn morning,” said Charles. “I can’t even sing in English, no more.”
Even though he left the studio, Jennings is still credited in the song for participating in the recorded chorus.
[RELATED: Behind the Song Lyrics: “We Are the World”]
4. Walking Off Tom Snyder’s Show (1998)
In September of 1998, Waylon was scheduled to appear on the Late Late Show with Tom Snyder. Jennings wanted at least half of the one-hour time slot on the show, but when the segment with radio personality Dr. Laura Schlessinger started going over and cutting into his time, he walked off the set leaving Snyder and producers scrambling to fill his spot in 15 minutes.
“He’s sitting there watching Dr. Laura and Tom talk,” said Jennings’ wife Jessi Colter. “In 20 minutes, he [Jennings] says, ‘We’re leaving.’” Shortly after another segment started with Dr. Laura still on, Jennings got up and left the set.
Jennings’ departure left Snyder with an empty guest chair and 18 minutes of time to fill. “The guy just got on the elevator and left,” said Snyder talking to fill the empty time on his show. “I have never had anybody leave before they came on.”
5. Skipping His Country Music Hall of Fame Induction (2001)
Just one year before his death, Jennings was inducted into the Country Music Hall of Fame, but he never showed up. In true outlaw fashion, Jennings didn’t see it as one of the biggest honors one could receive from the country music community and skipped accepting the honor in person.
When asked what the induction meant to him, Jennings answered “Absolutely nothing, if you want to know the truth about it.” Years earlier the CMA told Jennings that he would never get into the Country Music Hall of Fame.
“They told me years ago I’d never be in the Hall,” said Jennings, “which was all right with me.”
Photo: Michael Ochs Archives/Getty Images
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