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“Rockin’ Years,” her duet with Ricky Van Shelton, reached No. 1 in 1991. It was Dolly Parton’s twenty-fourth. It was also her last chart-topper until 2006. Country radio kept moving away from her through the 1990s, even as her albums went on selling. Then, in early 1999, Decca closed its Nashville office — leaving her without a record label for the second time in a single year. That July she had dinner with her longtime producer, Steve Buckingham. He told her that when bluegrass fans were asked which artist they most wanted to hear make a bluegrass record, they overwhelmingly named her. She told Billboard they were both shocked — then she realized she managed herself now and had her own label, so there was nothing to stop her. The whole album was recorded in Nashville by the end of August. Jerry Douglas, Sam Bush, Stuart Duncan, Bryan Sutton, Jim Mills and Barry Bales came to play. Alison Krauss, Patty Loveless, Rhonda Vincent, Claire Lynch and Dan Tyminski came to sing. The Grass Is Blue reached No. 198 on the Billboard 200. It won the Grammy for Best Bluegrass Album, and the International Bluegrass Music Association named it Album of the Year.

Dolly Parton’s Bluegrass Turn That Changed the Conversation

By the early 1990s, Dolly Parton was still one of country music’s biggest names, but the charts were changing around her. Her duet with Ricky Van Shelton, “Rockin’ Years,” reached No. 1 in 1991 and became her 24th chart-topper. It was also her last No. 1 until 2006, a long gap that quietly signaled how far country radio was drifting away from her even as her albums continued to sell well.

Then came another setback in 1999. Decca closed its Nashville office, leaving Dolly Parton without a record label for the second time in a single year. For many artists, that kind of disruption can stall everything. For Dolly Parton, it became a turning point.

That July, Dolly Parton had dinner with longtime producer Steve Buckingham. He told her something that surprised them both: when bluegrass fans were asked which artist they most wanted to hear make a bluegrass record, the overwhelming answer was Dolly Parton. It was the kind of statement that could have stayed a flattering dinner-table story. Instead, it lit a spark.

Dolly Parton later told Billboard that she and Steve Buckingham were shocked at first. Then she realized something important: she managed herself now, and she had her own label. There was no one left to tell her no. That freedom mattered. It meant she could follow the idea immediately, without waiting for approval from a company that might not understand what she wanted to do.

A Record Made Quickly, and with Purpose

The album came together fast. By the end of August, The Grass Is Blue had been recorded in Nashville. The session list reads like a gathering of bluegrass and roots music royalty: Jerry Douglas, Sam Bush, Stuart Duncan, Bryan Sutton, Jim Mills, and Barry Bales all came to play. Alison Krauss, Patty Loveless, Rhonda Vincent, Claire Lynch, and Dan Tyminski added their voices. The result was not a novelty project. It felt focused, alive, and deeply connected to the music’s tradition.

What made the album special was not just the guest list. It was the sense that Dolly Parton was stepping into a style that had always lived near the heart of her music. The songs sounded like someone returning to a home she had never fully left.

Sometimes the boldest move is the one that sounds the most natural.

The Response

The Grass Is Blue reached No. 198 on the Billboard 200, a modest placement by mainstream standards, but the album’s real impact came elsewhere. It won the Grammy Award for Best Bluegrass Album, and the International Bluegrass Music Association named it Album of the Year. Those honors confirmed what listeners already felt: Dolly Parton had not simply made a side project. She had made a respected bluegrass album that stood on its own.

In hindsight, the story feels bigger than a chart position or an award list. It is about an artist refusing to be defined by the industry’s shifting tastes. When the doors closed, Dolly Parton opened another one. And when she did, bluegrass music welcomed her in.

 

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John Denver Wrote “Annie’s Song” in 10 Minutes — But Annie Named a Different Song as Her Favorite

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People once expected Kris Kristofferson and Merle Haggard to clash. Nearly fifty years later, Kris stood at Merle’s funeral and sang him home. When they first met, Kris was the long-haired songwriter some in Nashville saw as a hippie. Merle was already one of country music’s biggest stars. People expected them to be at odds. Kris remembered it differently. “From the first handshake we were best friends,” he later said. That friendship lasted for decades. They toured together, and less than two months before Merle died, they were still sharing a stage in California. Merle died on April 6, 2016, his 79th birthday. Three days later, at his private funeral, Kris picked up his guitar and sang “Sing Me Back Home.” It was one of Merle’s most personal songs, drawn from his memories of San Quentin and a fellow inmate facing death. Nearly fifty years after that first handshake, the man everyone expected Merle to clash with was there for one of his final goodbyes.

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Hours before Buck Owens died, he was already walking toward his car because he felt too sick to perform. Then some fans from Oregon stopped him. Buck had eaten his favorite chicken-fried steak at the Crystal Palace in Bakersfield, but told his band he wasn’t feeling well enough to go onstage. On his way out, he met fans from Bend, Oregon, who told him how far they had traveled just to hear him sing. Buck turned around. “If somebody’s come all that way, I’m gonna do the show and give it my best shot,” longtime Buckaroo Jim Shaw remembered him telling the audience. Buck performed that night, then went home. A few hours later, he died in his sleep. He was 76. There had been no farewell announcement. No one knew they were watching his final show. Buck had been too sick to play. But when he heard how far those fans had come, he turned around and gave them the show. It turned out to be his last.

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John Denver Wrote “Annie’s Song” in 10 Minutes — But Annie Named a Different Song as Her Favorite

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People once expected Kris Kristofferson and Merle Haggard to clash. Nearly fifty years later, Kris stood at Merle’s funeral and sang him home. When they first met, Kris was the long-haired songwriter some in Nashville saw as a hippie. Merle was already one of country music’s biggest stars. People expected them to be at odds. Kris remembered it differently. “From the first handshake we were best friends,” he later said. That friendship lasted for decades. They toured together, and less than two months before Merle died, they were still sharing a stage in California. Merle died on April 6, 2016, his 79th birthday. Three days later, at his private funeral, Kris picked up his guitar and sang “Sing Me Back Home.” It was one of Merle’s most personal songs, drawn from his memories of San Quentin and a fellow inmate facing death. Nearly fifty years after that first handshake, the man everyone expected Merle to clash with was there for one of his final goodbyes.

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Hours before Buck Owens died, he was already walking toward his car because he felt too sick to perform. Then some fans from Oregon stopped him. Buck had eaten his favorite chicken-fried steak at the Crystal Palace in Bakersfield, but told his band he wasn’t feeling well enough to go onstage. On his way out, he met fans from Bend, Oregon, who told him how far they had traveled just to hear him sing. Buck turned around. “If somebody’s come all that way, I’m gonna do the show and give it my best shot,” longtime Buckaroo Jim Shaw remembered him telling the audience. Buck performed that night, then went home. A few hours later, he died in his sleep. He was 76. There had been no farewell announcement. No one knew they were watching his final show. Buck had been too sick to play. But when he heard how far those fans had come, he turned around and gave them the show. It turned out to be his last.

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CONWAY TWITTY FINISHED A SHOW IN BRANSON ON JUNE 4, 1993. BY THE NEXT MORNING, IT HAD BECOME HIS LAST. That Friday night, Conway was still doing what he had done for decades — standing in front of a country crowd and singing the songs that had made him one of Nashville’s biggest stars. After the show, he climbed aboard his tour bus for the trip back toward Tennessee. Nashville’s Fan Fair was ahead. He never made it. During a rest stop in southwest Missouri, Conway collapsed on the bus. He was rushed to a Springfield hospital, where doctors operated after an abdominal aneurysm ruptured. On June 5, Conway Twitty died from complications following surgery. He was 59. There had been no farewell tour. No announcement that Branson would be the last time. The audience had simply watched Conway Twitty sing, applauded, and gone home. By the next morning, they were part of a farewell none of them knew they had witnessed.