George Strait Tips His Hat to Billy Joe Shaver With His Cover of “Willy the Wandering Gypsy and Me”

by Clayton Edwards
(Photo by Matt Winkelmeyer/Getty Images for iHeartMedia)

Live Forever: A Tribute to Billy Joe Shaver will hit shelves and streaming services on November 11th. The record features a laundry list of country music’s finest performing Shaver’s songs. Miranda Lambert, Willie Nelson, Lucinda Williams, Rodney Crowell, Amanda Shires, and plenty more contributed songs to the collection. Today, we get to hear George Strait’s rendition of Shaver’s “Willy the Wandering Gypsy and Me.”

This is more than just a stellar cover of one of Shaver’s best-loved tunes. It’s one Texas legend tipping his hat to another and if that doesn’t give you a warm fuzzy feeling, I don’t know what to tell you.

George Strait is one of the best-selling artists in the history of country music. To many fans, he’s the King. Even folks who aren’t fans of the genre know his name. Here, he pays tribute to one of the integral members of the early Outlaw Country movement.

Billy Joe Shaver didn’t get the public recognition that guys like Waylon, and Willie, did. However, to those who know, he’s a hero. Before Shaver’s death in 2020, Willie Nelson called him “the greatest living songwriter.” Other greats including Johnny Cash also counted Shaver among their favorite songsmiths. To have George Strait cover one of his songs today is like shining a spotlight on Shaver’s work.

It’s One of George Strait’s Favorite Songs

Freddy Fletcher who co-produced the tribute album explained how George Strait ended up choosing this song. “About three years ago, Lou Messina, the promoter, had a big birthday party down in our studio. George came in and sang ‘Willy the Wandering Gypsy and Me’ and it blew me away.”

Later in the evening, Fletcher told George Strait, “I can’t believe you did a Billy Joe Shaver song.” Strait replied, “It’s one of my favorite songs.” That stuck with Fletcher.

So, when it came time to assemble the artists for Live Forever, he called Strait who said he’d appear on the album if he could have this song. “I had a lot of work on my end because there was a lot of people vying for certain songs, but there was no way I was gonna tell George Strait he couldn’t have that song,” Fletcher recalled.

About contributing to Live Forever, George Strait said, “It was an honor to be a part of this tribute to one of Texas’s best. He got down deep into the very soul of country. RIP Billy Joe. See you down the road amigo.”

It’s an Important Song

Billy Joe Shaver wrote most of the songs on Waylon Jennings’ iconic album Honky Tonk Heroes. Before that, though, he was a relatively unknown songwriter. His involvement in the Outlaw Country movement started with a chance encounter.

This is how it happened according to Billy Joe Shaver. It was the summer of 1972. Like many country fans and artists in Texas, Billy Joe was attending Dripping Springs Reunion on Hurlbut Ranch. To escape the sun, Shaver was inside a camper trailer with a few other guys. They were swapping songs and shooting the breeze. Billy Joe picked up the guitar and started to sing when Waylon Jennings popped out of the camper’s bathroom asking, “Whose song is that?”

It was Shaver’s song. He was playing “Willy the Wandering Gypsy and Me.” That interaction led to a partnership that would help shape the face of country music.

In short, George Strait proved once again that he knows how to pick a song.