photo by Mikey Webb

photo by Mikey Webb

Whey Jennings, Turning Heartbreak into Good Medicine with His Music.

                You hear the name Jennings, and you know instantly the family lineage, Waylon and Jessi and their Country music legacy. Whey Jennings, Waylon and Jessi’s grandson, pays homage to their legacy, and honors a promise he made to his mother on her death bed, in his music; whilst he fights personal demons, heartbreaks, and tells the tales of a true gypsy travel, All the while he turns heartbreak into medicine for the people, through his songs. Jennings has been labeled as a private person, and difficult to know by some, and yet I found him to be warm, and open; sharing about his family history, and his own journey with music. In many ways, Jennings is a sage, and has many revelations to share.

                Whey Jennings is playing with a new band, although he has been touring in and out of the past seven years. He recently finished up a performance with Honky-tonk artist Jackson Taylor, and is set to record a new album, scheduled for release this Fall, “Voices from the Gallows.”

                I asked Whey to talk about the new album, and what inspired him to write it, and he shared with me, “about two years ago I got my heart ripped out by a woman, who I loved very much at the time, and I still kind of love her, you know. What happened was I was sitting in a room and my guitar player; he was going through some things with his old lady too. He wasn’t the happiest person, and he started playing guitar, and I turned on my phone to record, and we recorded about three days’ worth of music on that thing.”

                Whey shared the inspiration behind the album title, “Voices from the Gallows,” which is also the title track off the album, and a favorite for Whey. “My Favorite song is called “Voices from the Gallows” which is the name of the album, and the way that song is written is weird because the pedal was still on, (when guitarist Danny Thompson was playing) and he was tuning his guitar, and it was making an eerie sound when he was doing it, so he started singing to it. Whenever I heard it, I could just picture a man walking to the gallows, you know. I put myself in that man’s position, and just left myself feel whatever I was feeling, and it came out really good.  It’s not a Country song, it’s not a Rock song, it’s just stops you in your tracks and makes you think about what you are doing I guess”

                For Whey this album is his breakout album, from the Traditional Country music he was raised with, to creating something all his own. Whey spoke about the creation of the album, saying, “The next album is going to be a full band album, and everybody I’m working with are my brothers, and we have all been through a lot, but we are all on the same page with everything. If you can get wild and crazy all on the same page that’s a rare thing.  I’m really looking forward to what people think about it, these songs right here are my songs, and they are done the way I would do them, and they are all me, I really hope people enjoy it”. He went on to say, “ I really love singing my grandfather’s music, and I do it every night, but I am working on music and creating something of my own, and that makes me feel something, and if I feel it, ya’ll are going to feel it too.” 

                Whey plans to release the album on November 7th, of 2018, if plans go accordingly. The date is special for Whey, as it was his late mother, Katherine’s birthday. Whey cites Katherine as his biggest fan, although she hardly got to see him play. Whey took to touring seven years ago at Katherine’s request. Whey spoke about Katherine’s encouragement for him to pursue music, “my momma was always on me about trying to do something, and I would always blow it off, but on her death bed she made me promise. It took me a year after she died to even try it, but when I did it just stuck I guess”

                Whey shared his mother’s advice to him, “she told me I’d make it, and I should just go out there and be like there I am, and I’d make it, and I was like,” no I don’t think your right”. However Whey reflected, “God Damn if she wasn’t right”.  Whey shared that he often sang and listened to the large record collections that Katherine owned, with her. 

                When asked Whey’s advice to his fans, Whey has come full circle from the young man who once doubted his mother’s prompting, to pursue music. Whey shared advice which echoed the advice his own mother gave him. Whey spoke, with a hint of season and wisdom in his voice, stating, “If you don’t think you can do it you can’t, if you do think you can do it you can, and there is nothing in this world that is  going to come up to your door, and knock on it, and jump in your lap. One thing you got to do to make it in the music business; you may not get a record deal, but look up bars and book shows, you’ve got to have a band of course, put some gas in your truck, and haul ass down the road, and just keep going, and make as much racket anyway you can, everywhere you can.”


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                That advice is exactly how Whey has lived for the past seven years. Whey does not discriminate and travels to, and performs where ever the music takes him, and people want to see him play. He shared that mentality by saying “I go about this different than most folks do, most folks go somewhere and make music and work their way out, I just sort of took everything I could get, and play everywhere I can get, mostly.  I’ll do shows in the middle of nowhere where people don’t even do shows.” For Whey it is getting to know the fans and making them friends in the process. Whey comes in through the front door, and he is not someone hiding inside his tour bus. Whey talked at length about his relationship with his fans.

I come in through the front door and set my equipment up, I go out front and I meet everybody, and at the end of my first set I introduce my guitar player, and my bass player; they do a couple songs, and my drummer; and after that I go shake everybody’s hands, and get to know them. When you go out there and you meet everybody, and you look in their eyes you know what you’re dealing with, you meet everybody, and find out what they are expecting, and what they are not expecting, and what they need to hear. I wanted to go out there, and I wanted the voices in their heads to tell me what’s going on.


Whey shared that at first, he took to meeting the fans and shaking their hands to overcome nervousness on stage. One would think that being the grandson of Waylon Jennings, and having music in the blood that it would be effortless for Whey. One would assume that Whey grew up on the back of a tour bus, for Whey that was not always the case. When asked about his childhood Whey remarked, “It’s been different, my mom and my dad got divorced when I was about three years old, and my momma raised me in Texas, and I went back and forth, and back and forth, and it was like living two lives, you know.  I went back to Texas and there was no music around hardly, and then when I went to Tennessee to visit, there was music everywhere, and every time I would see my grandparents it was like at airports and up at Billy Bob’s Texas, backstage there, and we would get on the bus and go for a little while, and then head back. You know, I am fortunate for it, but I was an old age before I realized what was going on and it didn’t really affect my childhood, you know what I mean.” For Whey as a child he wanted to be a Dallas Cowboy. Stories about Whey tell a tale of how he took the mic, on stage at the age of eight, and picked it up and began singing “Momma’s Don’t let you babies grow up to be Cowboys” but Whey also tells a story of how, performing with grandpa Waylon he froze, and put music aside for some time. Whey remembered, “, when I was 13 I went to one of his shows, and I came out there and I froze, and it scared the hell out of me, so I went back home and I got a job and I worked my whole life.  I was a cabin installer, and I worked on a cotton farm for like ten years, but I always kept singing you know, at barbeques and joking around,” Whey remarked that he was a “closet singer”. 

Whey shared what it has been like for him the past seven years pursuing music professionally.

My mom asked me to do this seven years ago, before she died and I never thought that music would change my life the way it has. It’s been an emotional rollercoaster the last seven years.  I’ve had some great times, and I’ve been on top of the world, I’ve had some low times; I’ve been on the bottom of the barrel. My heart feels so much better, I feel like I’m using that organ now.  I’m not used to using it, it’s taken a damn beating and its stretches and retracts, and all that kind of stuff.  I can be up there singing a song and all of a sudden feel like crying, but it’s such a good thing, I’ve found something that I have been missing my whole life, I know it’s there, and I’m going to do something with it;  but I just hope everybody likes what I do beyond that.

When asked if he had received any advice from the Jennings side of the family, Whey shared, “My daddy told me. “ listen, the music business is not what you think it is, they show all of the good stuff, they film all the good stuff and put it out there, but it is a hard road”, you know what I mean?  In between is a lot of headache, a lot of driving, it is rough, and he warned me about a lot of that, and I told him, “ I am doing this”, and he is right it is hard work, but its work”. Whey also shared he was advised, “Don’t let anybody change you, what you are is what you are, everything else is all but good.”

Whey shared a bit about his musical direction when he said, “What I want to do is go back to where music took a wrong turn and take a right turn”. Whey said that in relation to the loss of appreciation in the Country music industry for Traditional Country. Whey went on to say, “I don’t see why in order to have this new genre they have, they had to completely kill another genre, was there only so much room for genres? I don’t get it, because I loved the way my grandfather sounded and my voice sounds a little bit like his” Whey discussed the contrasts between himself and his grandfather’s music by saying, “ I try to Rock it up a little bit more, because I love Rock N Roll, my grandfather he did not want to lose the Country, or the Country fans because he loved Country music and he was good at it, you know what I mean, I am good at it too, but I don’t want to be something that has already been you know?  My granddaddy did that great, he was the best at it so I just want to do my version of it, you know, just like anything when one generation grows the next generation is the same thing but they are going to improve on what you have already done, I want to complement it not tear it apart.”

When asked about walking in Waylon Jennings shadow Whey thought for a bit and said, “It’s a big deal you know what I mean; it bothers me; I fight with it back and forth. I love my grandfather he was a good man, and he was like a big old kid and we connected, well let’s put it that way, I know that he would want me to break out of his shadow but at the same time I don’t want to”

                Whey reflected on the music business today, and the fact that so many singers do not write their own songs. For Whey he not only writes his songs, he has lived what he writes about. Whey shared about the music industry, “When you hand (a song) to a fifteen year old kid and say, “go sing this” it’s not going to come out that way.  It’s not going to come out the way I feel it you know what I mean, you’ll be able to dance to it, and it’s going to sound good, and there will be pretty people up there doing it, but it is going to be hollow because the person who is giving it to you, they don’t even know where it came from.  Somebody gives it to you, and its like, “we are just going to do this now.”  Whey’s songs are far from Pop Country, and his sources of his inspiration can be traced.

                When asked about what inspires Whey to write he reflected, “Pain, I’ve been through some things in my life man, you know, I’ve built some walls, I’ve dug some holes, and I’ve done right and wrong;  when regret sets in and remorse, something things like that, you have got to get that out of you, your poisoning your body and you can take that poison and turn it into a potion and actually make people feel better, and make them feel that they are not going through it alone. That is the best medicine on earth”.  When asked Whey shared that he could not imagine his life now, without music, Whey said, “I don’t think I could ever go back to doing something different because I love creating music, it comes out of what I have been through, and giving it to people in a way it makes them feel better, you know what I mean.”  For Whey Jennings fans they know exactly what he means, and he gives a bit of himself in every song he does. When asked about music, Whey agrees it has been a journey for him, and that it “hurts like hell”. However, Whey continues to turn that pain into medicine, medicine which has the power to uplift, move, and to soothe someone else’s heartache. When asked what Whey would like to be remembered for he thought for a while, and finally said, “I would like to be remembered as somebody who screwed up everything in his life once, and went back and did it right.  How can you do it right, if you didn’t do it wrong?” For Whey he would like his fans to remember his music and to be inspired to create their own. “I want somebody to remember something I did and make something better out of it than I did, you know” Whey shared. 


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                Whey is a true troubadour of his trade, what you see is what you get with Whey, and he is as authentic as they come. He has had support from other seasoned song writers in his genre like “Bad ass” Billie  Gant, and Michael Stacey. However, he has not had support from major record labels or radio. Whey has taken to the road with momma’s advice, and grandpa Waylon’s legacy, and is creating a legacy all of his own. You have only to listen to one of Whey’s songs, that lonesome sound in his voice reflective of Waylon’s, but with a tone all his own; and to hear the tales he tells; and to feel the heartbreak, and revere in his music to know he knows what he sings about first hand. To see him perform that raw emotion emanates from him. In the moments he shares in his music you might just find yourself, you might reflect on something you have not thought of, or perhaps something pulls just a little more, on your heart strings; through that Whey has done just what he has set out to do, to take what he feels, and to make you feel it too.


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