Today, Waylon Jennings is considered to be one of the greatest country artists of all time. But it wasn’t an easy road to stardom for the “Good Ol’ Boy.”
15 years passed between the release of Jennings’ first single, “Jole Blon,” and his first number one hit, “This Time.” After the release of “This Time,” Jennings managed to score many more number ones and Top 10 hits on the charts up until his death in 2002.
Even though it took some time for Jennings to secure a number one hit, he was quick to make a name for himself in country music. One of the first singles that helped make him a household name was his 1965 release off of his second album Leavin’ Town, called “Anita, You’re Dreaming.” The song was one of Jennings’ earliest hits, and peaked at the 17th spot on the country chart in the U.S.
Co-written by Jennings and Don Bowman, the song sounds quite different from some of his later material. Arthur Michael Striessguth describes the song’s style in his book Outlaws: Waylon, Willie, Kris, and the Renegades of Nashville:
“One of the early hit singles, ‘Anita, You’re Dreaming’…found Waylon in a serious and cautious vocal mode that remembered Jim Reeves, only this time with a trace of Marty Robbins, whose famous Latin sound rose up on Waylon’s albums more than a few times in the 1960s.“
Jennings was still in the process of developing his own sound at the time that he released “Anita, You’re Dreaming.” As Stephen Thomas Erlewine of All Music wrote, the Leavin’ Town album as a whole showcased Jennings working on “developing a distinctive blend of country and folk .”
Since “Anita, You’re Dreaming” is not as well-known as some of Jennings’ other songs, it’s a rare thing to find footage of him performing it live. But we managed to come across a spectacular, full-color clip of Jennings performing it during a televised appearance.
For those used to watching Jennings’ performances from later in his career, the fresh-faced young man singing in this clip will look unrecognizable to you. But the one thing that can’t be mistaken is Jennings’ voice, which was just as gritty and powerful as you’ve always known it to be.
Jennings ended up delivering a brilliant performance of his early hit, proving that he had all the makings of a major country music star. What a treat it is to watch this footage with the knowledge that he went on to become just that and so much more!
Scroll down below to witness history unfold before your eyes as a young Jennings sings “Anita, You’re Dreaming.” There will never be another one like him, that’s for sure.