In 1966, a baby-faced Waylon Jennings, who was fresh off the release of his debut RCA Victor album Folk-Country, took the stage at The Porter Wagoner Show.
He performed his first two radio singles “Anita, You’re Dreaming” and “Time to Bum Again,” which also resulted in his first significant chart success as both peaked at #17 on the Billboard Hot Country Songs chart.
“Time To Bum Again” was written by Harlan Howard, and “Anita You’re Dreaming” was written by Don Bowman and Waylon.
Of course, this was the very beginning of what would ultimately become a decades-long career as the face out outlaw country, and in some ways, he’s barely recognizable without the beard and long hair that became part of his signature, rugged look.
It’s also pretty rare to see Waylon in a full suit, which is another neat part about this vintage performance.
And even in footage from 57 years ago, Waylon’s unique and distinct voice comes through so perfectly… I mean, it’s hard to argue he wasn’t destined to be a massive star when you watch this, even from so early in his career.
Do yourself a favor and check it out:
Watch Waylon Jennings’ Heart-Melting 1975 Performance Of “It’s Not Supposed To Be That Way” At The Texas Opry
I mean, the last verse alone is absolutely brutal:
“When you go out to play this evenin’ Play with fire flies till they’re gone Then you rush to meet your lover Play with real fire till the dawn
It’s not supposed to be that way You’re supposed to know I love you But it don’t matter anyway If I can’t be there to console you…”
Second of all, I think it’s pretty safe to say that Waylon had more charisma in his pinky finger than most people have in their entire body, and the way he sings this song just takes it to another level.
“It’s Not Supposed To Be That Way” was included on his 1974 album This Time, which he co-produced with Willie Nelson, who originally penned the song as a solo-write.
Willie released it on his 1974 Phases & Stages record, and the duo would later include Willie’s version on their classic 1978 collaborative album, Waylon & Willie.
Waylon knew how to melt a heart and give every single performance everything he had no matter what. I’ll always be a firm believer that he had one of the greatest voices that has, or will ever, exist in country music.
It’s just one of those gut-wrenching sad country songs that somehow simultaneously has healing powers, because you don’t even need therapy after you listen to it on repeat 20 times over no matter your mood… and of course, leave it to the great Willie Nelson to pen such a song.
’70s country is just so damn underrated, and this video of Waylon’s performance at The Texas Opry, which also features him singin’ a little “Slow Rollin’ Low” in 1975, is proof: