He’s carrying on the family tradition with a new single from his upcoming Jekyll & Hyde album.
Whey Jennings is proud of his lineage — he’s the grandson of country music icons Waylon Jennings and Jessi Colter — but he’s determined to make a name for himself on his own merits.
So far, the Nashville recording artist and singer-songwriter for Dirt Rock Empire is making admirable progress in that direction, with a new album, Jekyll & Hyde, set for release Aug. 23, and another single from that album, “Girl on a Fast Horse,” now available.
But Jennings is the first to admit he’s encountered a few speed bumps, and survived self-inflicted setbacks, along the way.
“Out of 43 years on this earth,” he says, “I lived 38 of them in the darkness. I was pretty well a functioning drug addict and an alcoholic. I found the light four years ago by the grace of God. I have a beautiful wife who has also stood by my side, and six beautiful children who continue to love me. A wonderful manager who I call my Momager, Mrs. Tammy Carolus. I’ve decided to dedicate this LP and my life to them.”
Here’s the C&I premiere of the official music video for “Girl on a Fast Horse,” featuring Jennings and Charity Bowden.
We recently spoke with Whey Jennings about making music, staying sober, and appreciating life. Here are some highlights from our conversation, edited for brevity and clarity.
Cowboys & Indians: Do you think of yourself as a traditionalist in terms of country music?
Whey Jennings: Well, yeah, I would say I was a traditionalist. But I like to build on tradition as well.
C&I: What was the inspiration for “Girl on a Fast Horse?”
Jennings: I’ve always loved love songs. A friend of mine, David Wade — who’s also my manager, actually — he’s a songwriter and he has a bunch of songwriter friends. And they brought me this wonderful song. It was a great idea in the direction it was headed. I made a few tweaks to it here and there, and I decided it’s going to be a victory song of love. You get the girl. There's a lot of love songs where you don’t get the girl. You know what I mean?
C&I: Yes, we’ve heard plenty of those.
Jennings: But on this one, I wanted to get the girl, and I want it to be kind of inspirational to people who have love in their heart. Because a lot of times love songs don’t have a happy ending. They turn into a “This is what I was going after, and I didn't get it” kind of thing. You know what I mean? But this one, he caught the girl on the fast horse, and I think it’s a beautiful thing.

C&I: Do you ever feel compelled not to record a song because you feared people might accuse you of sounding too much like your grandfather?
Jennings: No. I used to, but nowadays, I’m just going to be myself. If people think that I sound like my grandfather, that’s whatever they think. I’m not going to be someone other than who I am. I just sing songs the way I feel, and I sing the songs that I feel like relate to me in my life. And if that reminds people of Waylon Jennings — hey, I mean, there’s no way to get around genetics. It’s just impossible to do. I've never woke up in the morning and said, “Hey, today I’m going to sing a song, and I’m going to make sure it sounds like Waylon Jennings.” That’s just not the case. I want it to sound like Whey Jennings. Whey Jennings does happen to be the grandson of Waylon Jennings. There's nothing I can do to change that.
I guess the best thing I can say about that is that I don’t understand why, in any other profession on earth, when your family follows in your footsteps, it’s is considered honorable. But in the music business, if you follow in your family’s footsteps, it’s riding coattails. I’ve never understood that. Not ever. I try my best to be me at all times. You know what I mean? I've been blamed, accused of riding coattails. I’ve been told I’m not as good as my grandfather. I’ve been audited. But I’ve never actually set out to be as good as my grandfather. I’ve just only ever set out to be as good as I can be at what I do. And that’s my only goal in life. Whether I sound like him or not, that’s a byproduct of what I’m trying to accomplish.
C&I: The title track for your upcoming Jekyll & Hyde album is a great song, with a sensational music video. But they’re both kinda-sorta autobiographical, right?
Jennings: Somewhat, yeah. I mean, we all have our inner demons. And what I was pretty much going for was trying to show people what would happen if your inner demons win. You know what I mean? I believe what we need to do is keep our inner demons at bay. We’ve got to really keep them in check, because it’s an ongoing struggle in anybody’s life. You could always make wrong decisions. But you can’t allow yourself to make bad decisions. We can’t ever find ourselves in that position.
C&I: Well, you seem to have conquered your demons. At least, as much as demons can ever be conquered.
Jennings: I’m winning the battle at the moment. Yes, I am definitely winning the battle at the moment. But you can’t ever get comfortable with that. You’ve got to know that it’s an ongoing fight. You’ve got to keep winning that battle. You can't just say, “Hey, I won,” and then sit down and then forget about the fight, or the fight will sneak up on you. So you’ve really got to keep everything in check constantly.

C&I: How do you feel right now?
Jennings: I feel great. I’ve got a great arsenal against my demons. I’ve got a beautiful family. I’ve got a wonderful support system, and I got the most Almighty God on earth, so there you go.
C&I: That’s a pretty strong team behind you.
Jennings: It is. It very much is.
Photography: Jonathan Galletti