Bizarre Billboards Pop Up In Hometown of Late Country Music Star originally appeared on Parade.
It’s not unusual for a legendary artist to have a symbol that fans know on sight. Elvis Presley had his iconic jumpsuits, Hank Williams his signature cowboy hat and Johnny Cash was always the man in black.
What is unusual, though, is to see that symbol emblazoned across billboards over two decades after their death.
Country music icon Waylon Jennings passed away in 2002 at the age of 64, just four months after he was inducted into the Country Music Hall of Fame. His fans were in for a shock on Monday, though, when Whiskey Riff reported that a reader had sent in pictures of billboards prominently featuring Jennings’ signature “Flying W” that had cropped up in his hometown of Littlefield, Texas. The billboards featured quotes from Johnny Rodriguez’s deep cut “The Cowboy”. Underneath the lyrics was the “Flying W” which, according to Jennings’ official store, is “more than a logo, it represents Waylon’s freedom in being an outlaw country musician.”
“My long, shaggy hair and the clothes that I wear ain’t fit for no big fancy ball,” reads one of the billboards. Another is emblazoned with, “I’m a cowboy who came here from Texas just to play you my music that’s all.” Though the lyrics come from Rodriguez’s hit, the addition of Jennings’ iconic symbol suggests a possible message to his fans–particularly when combined with their location in his hometown.
Just over a month ago on June 15, Jennings’ son, Shooter Jennings, 46, announced that he had discovered among his father’s old tapes a “plethora of music” from the “peak” of Jennings and his band, The Waylors, glory years, and with the help of four original band members, would be releasing three albums of his father’s previously unreleased music.
In response to a Facebook post of the billboards, one fan commented that they could come from “Shooter or someone in his camp” as only the star’s son “knows what’s in the songs.” There is no proof that “The Cowboy” or any other Johnny Rodriguez song will feature on the future album, but the timing of the billboards is curious, as are the chosen lyrics, which speak to the country star’s iconic rebel country-turned-outlaw image, as well as his humble beginnings.
Born into poverty in West Texas, Jennings first rose to fame in the 1950s as Buddy Holly’s bassist before moving to Nashville where his star rose for five decades as he performed alongside other country greats like Kris Kristofferson, Willie Nelson and Johnny Cash in the group The Highwaymen, won multiple Grammys and CMAs, and came to be known as the “outlaw” of Nashville.
No one has taken credit yet for the mysterious billboards. If there is a connection between “The Cowboy” and the upcoming new Jennings music, it seems fans will have to wait until October 3 and the release of Songbird to find out what it is.
Bizarre Billboards Pop Up In Hometown of Late Country Music Star first appeared on Parade on Jul 22, 2025
This story was originally reported by Parade on Jul 22, 2025, where it first appeared.
