One of The Highwaymen: Blake Shelton Reflects on His Dream Moment With Kris Kristofferson, Willie Nelson, and Merle Haggard

Kris Kristofferson won a total of four Grammy Awards during his career. His first Grammy was the Song of the Year award for “Help Me Make It Through the Night” in 1971. Two were Best Country Performance by a Duo or Group for duets with Rita Coolidge in 1973 and 1975. The final and possibly most important was the Lifetime Achievement Award he took home in 2014. That night, he shared the stage with Willie Nelson, Merle Haggard, and Blake Shelton to perform a string of country classics.

First, Nelson and Kristofferson, the two remaining members of The Highwaymen performed “Highwayman.” Then, Haggard and Shelton joined them on the stage for a rendition of “Okie from Muskogee.” The foursome finished their set with “Mammas Don’t Let Your Babies Grow Up to Be Cowboys.” Watch the iconic performance below. It starts at 1:15.

[RELATED: 7 Unforgettable Photos from Kris Kristofferson’s Long and Legendary Career]

Blake Shelton Reflects on Performing with Kris Kristofferson, Merle Haggard, and Willie Nelson

In 2017, the Grammy Awards celebrated its 60th anniversary. As part of the celebration, Blake Shelton looked back on the night he shared the stage with some of his musical heroes. “My manager called me and said, ‘You’ve got an offer to play at the Grammys’ and I was like ‘Whoa! Really? Again?’ and he goes, ‘From what I can tell, they pretty much want you to be one of the Highwaymen to be up there wither Merle, who now we’ve lost, Kristofferson, and Willie was up there. I will never forget this,” he said.

In 2014, Shelton spoke to The Tennessean about that night. “This is an absolute dream come true, well beyond being nominated for a Grammy,” he told the publication. They asked if being onstage with the country legends made him feel like “one of the team.” Shelton said it didn’t. “It doesn’t make me feel like one of them as I can’t imagine how I could be, but what I do know is that it does give me bragging rights to my generation,” he said.

Shelton wasn’t the only one who felt honored to be on the stage with Willie Nelson and Merle Haggard. “I feel like I’ve got to pinch myself up there,” Kris Kristofferson said. “It’s like I’m standing with the Beatles, and I’m treated with respect like I belong up there.”

Featured Image by Kevin Winter/WireImage