Whey Jennings – A Real Guy Descended From Country Music Royalty

Photo courtesy of Scotty Logan and Whey Jennings

Some surnames are fairly common. You could be born into a celebrity family and provided you kept a low profile for most of your life, there’s a good chance nobody would even ask if you were related to a superstar with the same last name as you, if your last name was common. Now, if you happened to eventually take up a similar career as that superstar, that might get people more curious.

A good case for this could be Whey Jennings. I was approached by his publicist to see if I would be interested in interviewing him. I was given a decent amount of background information about him, including the fact that he’s the grandson of two country music legends, Waylon Jennings and Jessi Colter. Mind you, not every artist bio includes a partial family tree, but not every artist comes with country music royalty in their blood either. Of course I was very interested in talking with Whey Jennings, but it left me in a bit of a rough spot.

Photo courtesy of Country Thang Daily/countrythangdaily.com

Don’t get me wrong, I have all the love and respect for both Waylon Jennings and Jessi Colter. They sit high atop the tallest peak when it comes to all things great about country music. I just needed to be careful how much I did or didn’t bring into our conversation about them. You’re never too sure about things like that, especially when you’ve never met the person you’re interviewing before. I mean, it was in his bio. He must have approved that, so I guess it wasn’t off limits, but then again, I’m sure he gets asked about it all the time. When does it get to be too much? Or, on the other hand, if you skirt the topic altogether, you risk offending someone. It’s a gamble.

I decided to forego my typical order of asking questions and jump right into that, but I also had two more obstacles. First, it was a phone interview. Always more difficult. You can’t read body language. You can’t see any eye rolls or looks of boredom or disgust. Secondly, when I did get the call, we were on an extreme time crunch. Jennings was at a gig up in New York and the General Lee, the car from the Dukes of Hazzard TV show, had just arrived, so he had to go handle that. I didn’t want to keep him long. I had to do some last minute shuffling of questions on the fly, but nonetheless, the one thing I kept the same was the family question. That was going to be first.

Photo courtesy of Do512

After Jennings told me he was in Bolivar, New York (which I found highly ironic, as it’s not that far from my hometown of Buffalo), and we talked a little bit about the show he was playing, I jumped right in. I told him I needed to address the elephant in the room and then we could move on. I asked him if he could inherit one trait from each of his grandparents, what would it be? His answer was quick and it was the same for both of them. “Their talent and their values.”

Photo courtesy of Jessi Colter Facebook

With that question out of the way we could move on and start from the beginning. Whey Jennings was born and raised in Texas. According to him, he had a really normal childhood. He did normal kid things. He said his grandparents really tried to keep their business and personal lives separate so he definitely had a typical childhood, with the exception of “going backstage and stuff”. When I asked him what he was doing as a teenager, he laughed and said, “as a teenager, I got into trouble.” I guess, to some extent, most of us did, so, maybe let’s say he even had a normal adolescence.

As far as the music he listened to growing up, it wasn’t all country as some might expect. “I listened to country from a young age from my Mom and Dad. Then I started to listen to hip hop, R&B, heavy metal and rock, but what I mostly was geared toward was country rock and the blues.” That led me to ask him whether or not he had ever been to the Shack Up Inn in Clarksdale, Mississippi which, if you’ve never been there, is right there in the heart of blues country and one of the most fantastic places on the planet. Jennings told me he had not been there, but I encouraged him to look into it because I really think he would love it there. I was turned on to the Shack Up Inn by someone else, and as many people as I can share it with, I will, but only if I feel it’s a place they’ll truly appreciate. It’s not for everyone, but I think it has Whey Jennings written all over it.

Shack Up Inn Photo by Daniel George

Jennings plays guitar, but you won’t see him playing it on stage often. He’s said he’s still working on perfecting playing and singing together, so he leaves the guitar to a pro and he handles the vocals. You have to respect an artist that can say that. He even said “I play pretty good, but I just need to keep working on playing and singing together.” Better to check the ego at the door and stick to what your strong suit is at the moment.

Video courtesy of Tammy Carolus and YouTube

You can definitely try and catch Jennings out on the road because he’s touring right now, but while you’re waiting to see him in the flesh, you’ve got the next best thing at your disposal. He has a new album out called Whey Jennings Live at the Nashville Palace. How perfect is that? The album was recorded live (obviously) right at the Nashville Palace in Nashville, except for one studio track that was recorded at Cooter’s Place in Luray, Virginia, and that’s a cover of “Southern Accents”, the old Tom Petty & The Heartbreakers song. Jennings explained, “We tried to do it a little different. We took a song with a good meaning and put a new feel to it.”

When I asked if he had anything else to add about the making of that record that might be of interest, he said on the day they recorded the live album his Dad passed away. It was only a few days before that, his Stepmom called him to say his Dad was in the hospital and might not be able to make the show, and sadly, on the day of the show he died during surgery. Terry Jennings, the eldest son of Waylon Jennings, passed away on January 25, 2019, just four days after his 62nd birthday. Although he left this world way too soon, he did leave something special. Terry Jennings has a book out that Whey Jennings said is “a really good book, you’ll like it”, and I am positive I will, because that is just the kind of book that I gravitate to. Music autobiographies are the first thing I look for when searching for new reading material. The book is called Waylon: Tales of My Outlaw Dad, written by Terry Jennings with David Thomas, and is available on Amazon and just about everywhere.

Image courtesy of Amazon

While you’re shopping for the Terry Jennings book, stop by cootersplace.com and pick up Whey Jennings Live at the Nashville Palace as well. It’s a great album, and while we’re talking about live shows like the one recorded at the Nashville Palace, you’re going to want to check out Jennings’s tour schedule so you can see him on stage for yourself. Pennsylvania’s his legal home, but he said the road is really where he hangs his hat most nights, and he’ll be all over the country this summer. While we were on the phone he was about to play in Bolivar, New York, then he’ll be on to places like Ohio, Michigan and Sturgis. Chances are good he’ll be somewhere near you. If not, you may want to take a little road trip. His schedule is right on his Facebook page (listed below).

If you do get out to one of Jennings’s shows, don’t be shy after the concert. Go say “hello”! He told me he’s always ready and willing to grab a photo with fans and sign autographs. Don’t let his outlaw exterior fool you either. This is one polite southern gentleman, at least he was on the phone with me. I would expect you’ll get the same experience at a show. A very cool guy indeed.

You might wonder what a guy who spends most of his life on the road does in his spare time, if he has any. In the case of Whey Jennings, he writes. A lot. That might not surprise you because he’s an artist who also happens to be working on a new album, but this might. “Lately I’ve been spending a lot of time working on my van, trying to get it livable to travel.” My reply to that was, “Well, that’s good to know. You’re doing real life things because you’re a real guy.” “I do a lot of real life things. I like to work. I’ve worked my whole life. I spent ten years working on a farm before I started doing this and I still like to work.” There you have it. Just because someone is born into a show business family doesn’t mean they’re spoiled rotten and never do anything for themselves. Jennings could have given me about a million other answers, but he told me he likes to work on his van. That’s about as real as it gets.

Yes, Whey Jennings is real. He’s authentically American. I asked him if I invited him over for dinner what should I serve? He told me he was from Texas so he liked meat, potatoes, greens and sweet tea. That’s not only American, that’s easy! I’ve not only discovered what I should serve if he comes over to my house, I’ve just told all of you what you should put on the menu if he drops in at yours. Just trying to make this country friendlier for everybody, one meal at a time.

Before I got on the phone with Jennings, I watched a video on YouTube of him and his grandmother, Jessi Colter, singing “Storms Never Last”, a song that Colter wrote and released on her 1975 album I’m Jessi Colter. That song was later done as a duet with her husband Waylon Jennings and covered multiple times by artists such as Miranda Lambert, Lee Ann Womack and John Prine, but in my own opinion, no cover was ever better than the original or the duet with Waylon.

Video courtesy of ANGELIsFun and YouTube

I had a new question, never asked before, prepared for Whey Jennings. If he were to select an up and coming female artist to sing a duet with, what would he be looking for in that female artist, and what song would he like to sing? He responded by saying, “Well, I’d probably do one we write because duets are kind of a big deal and you don’t want to do one someone has already done, unless you’re gonna do it better than they did, and if you do that, it’s already got a double negative to it. I’d probably like to write one, and the best female artist out here that I’ve come to meet and know is Jasmine Cain. She’s not really a country artist. Or Ashton Shepherd, she’s a real good friend of mine. I’ve also got an aunt that’s got a really good voice I’d like to do a duet with, or my Grandma. Yeah, my Grandma, she’s a great lady. She just gave me a ring of my Grandpa’s the other day, right there in Arizona. It’s cool, I ain’t took it off since.”

One thing Jennings wanted to make sure I got in before we ended our conversation was information about a festival in Shenandoah, Virginia August 10th and 11th. It’s the Cooter’s Good Ol’ Boys Fest at Shenandoah Speedway. I can understand why he didn’t want me to miss this after I looked it up. What a festival this is going to be! The lineup alone is worth it. Check it out. Of course, Whey Jennings will be playing. Then you have Wynonna & The Big Noise, Exile, Confederate Railroad, Billy Dean, Tom Wopat, Cooter’s Garage Band, Catherine Bach and more. There will be two stunt shows on Sunday, rides on the General Lee and even more. I want to go to this thing! All the details and ticket information are available at the link listed at the bottom of the page.

Image courtesy of Cooter’s Place

Finally, when Whey Jennings “Thinks Country”, what does he think? “Life, because that’s what country is, songs about life.”

After I proofread this interview, I was about to leave it as it was right after the quote above. I thought it was a good way to end it, but then I stopped and decided I couldn’t live with myself without adding something more.

There are many country artists that talk about country music being about real life. How could you not agree with that? I believe there are countless artists that have lived the real life and can create from that honest experience, but never have I talked to anyone that struck me as more authentically real as Whey Jennings. I think it was a combination of everything he said and how he said it, but more than anything, there was one aspect of our conversation that left an impression on me.

When Jennings talked about his family, I could feel how much he loved them. He wasn’t over-the-top about it. It was more of an understated way of letting me know they’re the most important people to him. He misses his Dad beyond measure. He adores his Grandma immensely. He misses his Grandpa and is so proud of him. He didn’t go on for days about them, but he just wanted me to know that he’s a real guy that has real feelings for his loved ones. You know, like real people do.