Country singer-songwriter Whey Jennings’s story contains multitudes, from the depths of addiction to finding sobriety and peace through faith, music, and the people he loves. The grandson of Waylon Jennings, he is putting his own stamp on country music, and helping others along the way. Jennings’s most recent writing is vulnerable and reflects the years of work he has put into improving himself — and the positive that has come from it. His upcoming full-length record, Jekyll & Hyde, due out August 23 on Dirt Rock Empire, includes songs about finding sobriety, country life, horses, family, patriotism, and the future.
Making His Way Back to Music
Country music has always been a part of Jennings’s life, growing up around his grandfather, Waylon Jennings, and grandmother, Jessi Colter. “I learned pretty young that I had a good vocal range. I went on stage with my grandfather a few times when I was young, and I had a great time,” he shared.
Once Jennings became a teenager, fear replaced the excitement he previously felt in the spotlight. One experience stands out in his memory. “I went out there one time when I was around 13 and was becoming a young man. It scared me to death,” Jennings remembered. “I froze like a deer in the headlights.”
Singing remained a part of Jennings’s life, but he didn’t foresee a career in it. As a young man, he moved from his childhood home near Dallas to the high plains of the Texas Panhandle, working on a cotton farm for many years. During this time, he struggled with addiction. It took a call from his mother, Katherine, to bring him back to music. “My mom told me that she had lung cancer. So I moved back to Dallas, and I spent the rest of the time she had on this earth with her. During this time, we talked about a lot of things, and she really wished I would do something with music. She had heard me sing my whole life, so I promised her I would do it,” Jennings remembered.
He returned to the business, but it would be several years before Jennings would find his footing and voice. Music is often the center of the party, and from bars to stadiums, alcohol and other substances are easy to come by. This puts musicians in a particularly unique and often difficult situation since their job requires constantly being around people who are letting loose. Jennings continued to struggle with addiction and admits to many missteps. “I made every mistake you could possibly make. The first mistake I made was thinking it was about a party and not about the music. It took me a lot of years to get over that,” he shared.
Fortunately, Jennings had supportive people in his corner, like his manager, or “momager” as he lovingly calls her, Tammy Carolus, and girlfriend Taryn Rae, who later became his wife. “They sat me down and told me they weren’t going to watch me kill myself, and at that point, I felt like I had a lot to lose because no matter what I didn’t have, I always had them,” he said. He entered rehab and started finding his unique voice as an artist. Jennings chose a faith-based rehab facility, which helped him further discover who he wanted to be and how to navigate his future. “I’ve always been a faith-based person, and I felt like that was the route for me. I went to church for all 28 days that I was there and took my guitar with me,” Jennings recalled. The community he found through music changed his outlook on the future, and he remembers learning Hallelujah, which Jennings now sings for his fans and has recorded on the new album. “We made some beautiful memories in there playing and worshiping God,” he said. Jennings’s wife, Taryn, knew how to support him through this difficult time. “When I met my wife, I didn’t have two nickels to rub together, but she helped me go out and do what I knew I needed to do in my own heart, to make myself okay with the life I’m living,” he shared.
A New Chapter
Taryn’s support was critical for Jennings, and he is now focused on supporting her and his six children while balancing his career in music. “I thank God every day for my family,” Jennings stated. “They have really rallied around me.” His children range in age, from his youngest daughter, who is three, to his oldest son, who graduated from high school in 2023. Being there for his youngest — Jennings always travels home between gigs no matter the distance or cost — and watching his older kids begin their own adult lives brings him great joy. “They don’t live the way I did when I was young. They’re all happy and thriving. To see my family thriving means the world to me. That’s what keeps me on the straight and narrow, knowing that I’m able to support my family in a way that I was never supported,” Jennings reflected.
Faith was important to Jennings long before he entered rehab and continues to be a guiding tenet. “My faith has always been there through life,” Jennings said. “I’ve never found a problem that I needed to solve and couldn’t find the answer to it within the walls of the Bible.”
Jenning’s new record, Jekyll and Hyde, comes out on August 23 on the Dirt Rock Empire label and is the culmination of these years of finding his voice and learning how to tell his story. He has released three studio EPs, including 2020’s Gypsy Soul, 2022’s If It Wasn’t for The Sinnin’, and 2023’s Just Before The Dawn. This will be his first full-length record, and Jennings is extremely proud to share it with the world. “When my kids are all grown, and I’m old and looking back on my life, I feel like I’m always going to look back to this album,” he shared.
While Jennings often sings about very personal subject matter, he maintains a grit and honesty that his fans relate to. His baritone voice carries, and like his grandfather, people pay attention when Jennings sings; this attention is going toward a worthy message. Songwriters often say to write about what you know, and Jennings is doing just that. With almost five years of sobriety under his belt, he knows first-hand how difficult it can be to get help and the positive that will come from it. Learning how to share about this in a meaningful way has been a journey in itself. “When I got out of rehab, the first thing I wanted to do was save the world. I found something I wanted to share with everyone,” he reflected. “You feel like you’re healed, but you still have a lot of healing to do before you can try to help others.”
Looking at the bigger picture and discovering how to share the negative things in his past in a way that can help others has taken time. “What I’ve learned is that I can’t just share about where I’m currently at in my music. I have to share about everywhere I’ve been through my music because I want to be able to relate to everyone. I can’t just disregard the life I’ve led. In this new album I was able to do that. I was able to touch on every area of life that’s important to me,” Jennings shared.
Taking responsibility for his own actions was critical. “You can dwell on horrible things. One of the biggest mistakes we make in our relationship with God is that we like to blame our lives on him,” Jennings reflected. “We forget about the fact that the first thing He gave us was free will, and with free will comes responsibility.” His own recovery story also helps him relate to others and meet people where they’re at. “I’ve come to realize that while it’s important to sing songs that push people toward recovery, that isn’t enough,” Jennings reflected. One of the most difficult aspects of recovery, and one of the primary areas where people will fail, is having a support system. Addiction pushes loved ones out of a person’s life and destroys trust, which Jennings experienced himself. One of the songs on his new album, Sleeves, explores this. “I’m trying to show people the life their loved ones keep hidden from them,” Jennings explained. “They hide the bad part of their lives and the good parts. Being an addict doesn’t mean you’re no longer human. I’m trying to open up the hearts of people who may be supporting an addict so they have a better chance of success once they decide to enter recovery.”
Jennings balances this serious message with lighter songs, calling on subject matter that has been a part of country music for generations. One of the tracks on Jekyll & Hyde, titled 10 Day Run, tells a wild, comical tale about an angry girlfriend who has reached her tipping point from being left home alone by her truck-driving man. Jennings enjoys creating music videos to pair with his songs, which bring the stories to life and give listeners a deeper look into each song. The video for 10 Day Run can be viewed on YouTube. Four singles from Jekyll & Hyde are currently available, and the full album will be released across all streaming platforms on August 23. Jennings is playing shows across the country, backed by an all-star band, including Pat Burr on guitar, Jack Dempsey on bass, and Cameron Dudley on drums.
Jennings is grateful to have a supportive team behind the scenes, including Jason W. Ashcraft, who handles publicity and PR; Tammy Carolus, who works as manager; co-manager David Wade, who also assists with song selection and co-writes with Jennings; Brandon Yannotti, representing Dirt Rock Empire; Gary Carter, record producer; and Gio Gotay, who produces videos for Jennings.
While a lot of the music business happens from a distance online, Jennings is passionate about connecting directly with his fans. “If people didn’t come out to my shows, I wouldn’t be able to support my family,” Jennings concluded. “I make friends with people while I’m at shows, and I don’t stay hidden. I love playing music, but I also love interacting with people and supporting my family. I’m grateful.” •
-Article by Lilly Platts