The Fascinating Story Behind the Final #1 Song from Waylon Jennings

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The final hit from a country legend is always a fascinating topic. The sad reality is that whenever a superstar reaches the end of their shelf life according to the cold and soulless assessment of country music’s Music Row, it comes fast and hard, and very often is final. It’s only a very few select performers who’ve had hits in multiple decades, let alone three or four of them.

For Waylon Jennings, his career was the tale of multiple seasons. After coming up playing in Buddy Holly’s backing band, Waylon became a big deal in Phoenix where the original Outlaw Bobby Bare discovered him and told him to move to Nashville. Waylon arrived in town and was marketed as a “country folk” performer by RCA producer Chet Atkins. However, one of Waylon’s early signature hits was the hot and twangy “Only Daddy That’ll Walk The Line,” which made it to #2 in 1968.

This song would portend the more hard country, and eventually Outlaw era of Waylon Jennings in the mid 1970’s when Jennings became one of the biggest artists in all of country music, minting #1’s left and right with songs like “Are You Sure Hank Done It This Way,” “Luckenbach, Texas,” and “Ain’t Living Long Like This.” Along with Willie Nelson, they revolutionized country music in the era.

By the mid and late ’80s though, all of this began to trail off, as it always does. In early 1983, Waylon Jennings had a #1 hit with “Lucille”—the old Little Richard rock n’ roll tune. Interesting note: Waylon once got fired as a DJ in Texas for playing too much Little Richard. It’s not that Waylon disappeared in the ’80s, but he struggled to find that same ’70s magic as country music itself was trying to find its footing, and so was Waylon in the post-Outlaw era.

Songs like “Never Could Toe The Mark” and “America” did well (both hit #6 on the charts in 1984), but his song “Will The Wolf Survive” (#5 in 1986) spoke to how artists like Waylon were becoming an endangered species at that time. The song goes,

Singing songs of passion
It’s the truth that they all look for
The one thing they must keep alive
Will the wolf survive?

Then came “Rose in Paradise.”

The song was co-written by country songwriter Jim McBride, who recently passed away, reigniting interest in the song. Though the big headlines about McBride were how he’d written hit after hit for Alan Jackson—an artist who very much symbolized the shrinking environment for old wolfs like Waylon heading into the late ’80s—McBride had also written songs for a lot of the country legends who came before.

Jim McBride actually wrote “Rose in Paradise” in 1983 with Stewart Harris. Underground country legend Randy Howard had the first recording of it, though it never became a big hit. Then Toy Caldwell of The Marshall Tucker Band heard it, fell in love with it, and recorded it, but his version never was released. Then Loretta Lynn of all people heard it, thought it was great, but not right for her. She thought it would be perfect for Waylon, and took it to his producer Jimmy Bowen.

Waylon then heard the song and loved it, but had just finish cutting a record, and wasn’t really looking for songs. Jim McBride recalled to Country Drive in 2023, “Waylon said, ‘You know we just finished, but tell those guys (writers McBride and Harris) that if they put that song under a rock, I promise I will’—and you know what a promise on Music Row is worth, basically nothing—‘I promise I will cut it next year.'”

Lo and behold, Waylon ended up keeping that promise, and it paid off in his next (and last) #1 song. “Rose in Paradise” spent sixteen weeks total on the charts in 1987. Here’s Waylon singing the song with a backup band that includes Chet Atkins, Emmylou Harris, Mark Knopfler, Michael McDonald, and others.


Nothing else sounded like “Rose in Paradise” when it was released. The song isn’t a twangy, Outlaw country song. It has more of an ’80s contemporary treatment. What’s so fascinating about the song is the intrigue in the story. Did the wife leave with the gardener, or was she buried in the garden by the husband for her infidelity? This is what kept audiences riveted.

Waylon would go on to have other big songs in his career. “Wrong” hit #5 in the charts in 1990, and though it only went to #22, many consider Waylon’s “The Eagle” as his final radio hit in 1991. This meant Waylon had Top 5 hits in the ’60s, ’70s, ’80s, and ’90s. Not a bad run for ol’ Waymore.

For a lot of Waylon Jennings fans and country music fans in general, “Rose in Paradise” holds a special place in their hearts. As country music was shifting away from all the legends of the past and the heroes from the Outlaw era, Waylon Jennings gave them one last song of passion. It was the truth that they all we’re looking for, and it was the one thing that must be kept alive in country music.

For one last time, the old wolf Waylon Jennings had a #1 hit.

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