MUSIC REVIEW | Waylon Jennings – Dreaming My Dreams (1975)

Where do you start when you’re making your first steps into not just an iconic artist, with dozens of albums from a decades long career, but an entire genre? A genre filled with iconic artists, and hundreds, if not thousands of albums considered classics? For me, I always start any major decision making with one question, “Is there a connection to The Dukes of Hazard?” When putting my Hazard Theory (patent pending) to the test in regards to 70s country music, it lead me straight to Waylon Jennings, and his album, Dreaming My Dreams.

Track 1 is the song that made me want to hear more of Waylon Jennings, know more about Waylon Jennings… And I didn’t even know it was a Waylon Jennings jam. I came to it via a cover by Chris Shiflett and the Dead Peasants. On an album full of songs I really dig, Are You Sure Hank Done it This Way? is by the stand out and by far the song I’ve listened to the most from Shifflett’s country outfit.

At first, I found Jennings’ version kind of underwhelming compared to the bigger, rockier sound of the Dead Peasants take. But the more I listen to the original, the more I can hear Jennings’ middle finger raising, outlaw edge, basically telling the country music industry to go fuck themselves. He was there to do things his way, not worship at the altar of the old guard, personified by Hank Williams. It’s all about respecting those who came before and everything they accomplished, without becoming a slave to it.

Country music loves to tell a story in the first person. Whether it’s autobiographical or complete fiction, all the I/me/my lyrics, combined with the worn out drawl of Jennings, makes those stories seem so real and lived in. Waymore’s Blues and I Recall a Gypsie Woman add to that authenticity by combining the first person storytelling with a slowed down approach that adds a little vulnerability to Jennings’ usual cocky swagger.

Then comes High Time (You Quit Your Lowdown Ways), exactly what you want from one of the Nashville shit kickers of the 70s. It’s upbeat and jaunty, with a story about an unapologetic prick who you can’t help but like. He’s selfish, he’s impulsive in all the wrong ways, he’ll never act on the song’s title, but I’ll be buggered if he doesn’t sound like a fun bloke to hang out with.

Things get really sentimental on Let’s All Help (the Cowboys Sing the Blues). When read as a title, I found it pretty hokey, corny and on the nose. But when you hear the tender music, big harmonies and the Jennings’ take on lyrics like, “So ladies, if they ask you don’t refuse, let’s all help the cowboys sing the blues”, it all of a sudden sounds a lot more genuine and sincere.

Of the thirteen tracks on Dreaming My Dreams, only three crack the three minute barrier. Usually, I’d see that as good thing. Brevity is generally underrated and under used in music. Too many bands feel like the key to making a good song is making an epic song. But punk has taught me that in my most cases, if a song hasn’t been good within the first two minutes, it’s probably not gonna improve with an extended length. But here, it’s one of the only weaknesses of Dreaming My Dreams. Almost every song fades out, mid chorus, with no definite ending. And in every case, I could have down with a little more. Give me another chorus, a little guitar break, then cap it off with an actual ending.

Late on the album, Bob Wills is Still the King sounds like the flip sideto Are You Sure Hank Done it This Way? I have no idea who Bob Wills is, but the crowd on this live recording sure does. I also now know, thanks to this song, that he was a Texan. Jennings’ reverence and the crowd’s apparent love is enough to make me think Wills is probably worth a listen.

As an introduction to the outlaw country dudes of the 70s, people like Jennings, Johnny Cash and Willie Nelson, Dreaming My Dreams is a pretty good gateway. I’m a novice in this genre, and while bands like Drive-By Truckers have made me appreciate the idea of country music a lot more now than I did only a few years ago, it’s a genre I still approach with a lot of caution. And Waylon Jennings seems like the guy to ease me into this world.

Waylon Jennings