It’s hard to imagine a time when the legendary Waylon Jennings didn’t sport facial hair and long, shaggy hair, but when he emerged onto the music scene, he was a clean-cut young man. In fact, he was even part of Buddy Holly’s band!
From there, he transitioned into rockabilly and eventually helped grow the outlaw country movement. He recorded upwards to 50 albums, not counting the 28 compilation albums and 16 collaboration albums.
He often duetted with his wife, outlaw legend Jessi Colter, Willie Nelson, and Johnny Cash, but there are a few that stand out from the rest. Although it was almost impossible to narrow this list down to just five songs, we wanted to feature five of the best duets Jennings ever recorded.
Let’s take a look!
5. “I’m Movin’ On” with Johnny Cash
In 2012, John Carter Cash, son of Johnny Cash and June Carter Cash, found lost recordings of his father’s from the early 1980s. The tracks, according to Paste Magazine, were recorded between 1981-1984.
“We were so excited when we discovered this,” John Carter Cash said in an interview with the Associated Press in December 2013, according to Paste Magazine. “We were like, my goodness this is a beautiful record that nobody has ever heard. Johnny Cash is in the very prime of his voice for his lifetime. He’s pitch perfect. It’s seldom where there’s more than one vocal take. They’re a live take and they’re perfect.”
He put the tracks together to make a posthumous album, Out Among the Stars, which included the Hank Snow cover “I’m Movin’ On” with Waylon Jennings. Although it’s one of Jennings’ lesser known duets, it’s by far, one of the best.
4. “Ain’t No Road Too Long” with Big Bird
We had to include this duet on this list because of how memorable and unique it is! How many times does a country outlaw legend sing with a life-sized puppet?!
Together, Jennings and Big Bird, from the children’s TV show Sesame Street, sang “Ain’t No Road Too Long” in the 1985 movie Follow That Bird, where he played a truck driver that befriends the large bird as he runs away from home.
Many other celebrities made cameos including legendary comedians Chevy Chase and John Candy.
3. “Good Hearted Woman” with Willie Nelson
Rumor has it, in 1969, when Jennings and his good friend Willie Nelson were staying at a motel together, they read an advertisement promoting Tina Turner as a “good hearted woman loving two-timing men”, a reference to Ike Turner.
They turned their little idea into a hit song for Jennings, which peaked at No. 3 on the country charts in 1972. In 1976, the two men recorded it as a duet and took it to No. 1!
2. “The Conversation” with Hank Williams Jr.
These outlaw legends released “The Conversation” in 1983, which is an ode to Hank Williams, Hank Williams Jr.’s late father. They imagine what he might think of today’s country music, and hope that he’s happy wherever he is.
Following Jennings’ death, Hank Jr. has sung the duet with Shooter Jennings, Waylon and Jessi Colter’s son.
1. “Storms Never Last” with Jessi Colter
Waylon and Jessi’s love story is one of country music’s most cherished. They were married in 1969 up until Jennings’ death in 2002. They recorded several albums together, but out of all their duets together, “Storms Never Last” definitely stands out.
A song about the hardships of marriage, which they know about first-hand, and knowing that their love will endure even the toughest of storms.
Which one of these duets is your favorite? Let us know in the comments!