On Wednesday, February 13, 2002, Waylon Jennings died at his home in Chandler, Arizona. He was 64 years old. That same evening, Willie Nelson had a sold-out show at the Feather Falls Casino in Oroville, California.
Willie did not cancel. He walked onstage and played for more than two hours, over 40 songs. He never stopped the show to deliver a eulogy. Some fans may have wondered why.
After the concert, a local reporter asked him. Willie Nelson looked up and answered without hesitation. He said he had mentioned Waylon, and that people already knew what Waylon meant. Then he explained that he mentions his friend in the songs he sings every night.
He also described Waylon Jennings in a way only a close friend could:
“He was ornery, mean and loveable, all in equal parts.”
To understand what Willie Nelson meant by “the songs I sing every night,” you have to go back to a motel room in Fort Worth, Texas, in 1969.
A Poker Game at the Fort Worther Motel
Waylon Jennings was staying at the Fort Worther Motel between shows when a newspaper ad caught his eye. It was promoting Ike and Tina Turner, and it described Tina as a singer of songs about good-hearted women loving good-timing men.
Waylon Jennings thought that line was a perfect country song title. He went looking for Willie Nelson and found him in the middle of a poker game. Waylon sat down, joined the game, and told Willie about his idea.
The two men worked out the song right there at the card table. Willie’s wife at the time, Connie, wrote the lines down on paper while the hands kept going around. That is how “Good Hearted Woman” was born. It was not written in a quiet studio or a publishing office. It was written between bets, by two friends who could not leave a good idea alone.
The No. 1 Duet They Never Sang in the Same Room
Here is the part many fans never heard. Waylon Jennings first recorded “Good Hearted Woman” by himself. Released in late 1971, it became the title track of his 1972 album and reached No. 3 on the Billboard country chart.
A few years later, Waylon decided the song should be a duet. But instead of booking a session with Willie Nelson, he took an existing recording and had Willie’s voice added in different places. Waylon later explained it simply:
“I just took my voice off and put Willie’s on in different places.”
Willie Nelson was nowhere near the studio when Waylon’s part was recorded. Even so, that version landed on the 1976 album Wanted! The Outlaws and climbed to No. 1 on the country chart in February 1976, where it stayed for three weeks. It was named Single of the Year by the Country Music Association. Later that year, Wanted! The Outlaws became the first country album ever certified platinum, for sales of one million copies.
The duet that helped define the outlaw movement had been stitched together in the mixing room, from a song written at a poker table.
“Stay Where You Are”
The friendship itself began years earlier in Phoenix, Arizona. Waylon Jennings was the star attraction at a busy bar there in the early 1960s, and Willie Nelson came to see him play. Willie liked what he heard. He later said Waylon played good guitar and sang good.
After the show, Waylon asked Willie a serious question: should he move to Nashville? Willie asked how much money he was making. Waylon said around $400 a week. Willie’s advice was short: stay where you are.
Waylon Jennings did not listen. He moved to Nashville in 1965 and signed with RCA. As Willie Nelson later put it, his friend went on to Nashville and did great.
Two Old Married People
Through the 1970s, the two men toured and recorded together. In 1978 they released their first full duet album, Waylon & Willie, which spent 10 weeks at No. 1 on the country albums chart. Its biggest hit, “Mammas Don’t Let Your Babies Grow Up to Be Cowboys,” was written by Ed and Patsy Bruce. Ed Bruce’s own version had peaked at No. 15. Waylon and Willie took it to No. 1 and won a Grammy for it.
Later came The Highwaymen with Johnny Cash and Kris Kristofferson, and a final duet album, Clean Shirt, in 1991.
They did not always agree. Willie Nelson often said they fought about almost everything. Waylon even wrote “Bob Wills Is Still the King” when he was annoyed with Willie, and Willie disarmed him by saying the song was right on the money.
“Waylon and I were like two old married people. We fought about everything… But we were great friends.”
When Waylon Jennings celebrated his sobriety in 1983 at a party hosted by Johnny Cash and June Carter Cash, Willie Nelson was on tour and could not attend. So he cut off his famous braids and sent them with Connie, who handed them to Waylon as a gift.
The Songs He Sings Every Night
On that February night in Oroville, the biggest ovation of Willie Nelson’s show came when he sang “Luckenbach, Texas,” the 1977 hit on which Willie sings the closing verse alongside Waylon.
Willie kept the promise he made to that reporter. In 2015 he took part in a tribute concert, Outlaw: Celebrating the Music of Waylon Jennings. And at Willie’s 90th birthday concerts at the Hollywood Bowl in 2023, his son Lukas Nelson and Waylon’s son Shooter Jennings sang “Good Hearted Woman” together, a song first written down on paper at a motel poker table more than 50 years earlier.
Do you remember the first time you heard Waylon and Willie sing together on the radio? We would love to hear your memories in the comments.