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An In-Depth Conversation With Country Artist Jenny Tolman

Photo courtesy of Jenny Tolman

Connections. I was introduced to Jenny Tolman by our mutual friend Zach LaChappelle. The first thing I asked when we got on the phone was how Tolman knew LaChappelle. “He was working at The Bridge Bar, which was inside the Renaissance Hotel. That was one of the places that I always played. It was one of the first places that I played one of my little shows at. He was always a really good supporter. He even got me to open for Love & Theft there when they had a private party. He’s just always been a great friend and supporter.” Although I never saw Jenny Tolman play at The Bridge Bar, I was there for other shows many times and that’s where I also met Zach LaChappelle. Small world.

That was a tiny matter of curiosity, and with that satisfied, I could move on and find out just what made Jenny Tolman tick. She is a rarity because she’s actually a Nashville, Tennessee native. Tolman said, “They call us unicorns.” Apparently, she also felt being born and raised in Nashville was a bit of an oddity in the country music world these days. She remarked, “I find it to be extremely rare, just like everybody else. I look at it as a blessing and a curse.” She laughed, and this wasn’t the last time she’d laugh either. This interview was saturated with laughter from both of us.

Tolman continued, “Obviously it’s a huge blessing to have grown up in this town and kind of know the ins and outs and not have to move away from family. You know, I was blessed also because my dad was a singer back in the 80s, so he had his foot in the music industry as well. So, I kind of grew up around music.” Of course, she did mention it could be a curse too. So, she elaborated on that with, “One of the funny things I found myself being, I don’t know if ‘jealous’ is the right word, but people that move away from their towns. They have this hometown fan base type of thing. In Nashville I do have somewhat of that, being from here, but it’s so funny because everybody moves here to make this their town.”

That’s something I never considered. Artists are always being told to build up their hometown fan base before they try and make it in Nashville, but what if your hometown happens to be Nashville? Those artists are competing with the world for their own hometown fans. Not an easy situation to be in when you look at it from that perspective. Jenny Tolman really opened my eyes on that.

“I’m so impressed by people that move here because I just would be so terrified to leave everything I know and the comfort of my family, and move to a new town where I don’t know anybody, to follow a dream, you know?” She continued, “I’m just always impressed by that because I don’t know if I could have done that, so I think God had me born here because he was like, ‘Oh, we’re not gonna put this extra stress on this one. She’s a little anxious as it is..'” All the while she was telling me this she was laughing. I couldn’t help but laugh myself. She has impeccable comic timing.

If you look at Jenny Tolman’s website, her bio calls her “quirky and wildly entertaining.” I could already tell that was an accurate description. Something else the bio says is Tolman is her generation’s Roger Miller. I asked her if she agreed with that and what her thoughts were about it. Roger Miller had some pretty big shoes, and anyone that’s going to step into them for a new generation, had to realize that. It’s quite a compliment, but it’s also a tall order.

Tolman gave me her take on all of that. “You know, for a long time I’ve been kind of modeling what I do after artists like Roger Miller and Dolly Parton. You know, Shel Silverstein is one of my favorite writers of all time. I’ve always found that they were able to be humorous while also being enlightening, which I find very fascinating.”

I found it fascinating that Tolman was such a big Shel Silverstein fan because I noticed she had a cover of his song “Still Gonna Die” on her There Goes the Neighborhood (Deluxe Edition) album. She was glad to hear I’d seen that and continued to explain how artists such as Silverstein have heavily influenced her.

Image courtesy of Jenny Tolman

“I’ve always kind of modeled myself after those types of artists, so I really wanted to have that same messaging of being able to make people laugh, but also being able to be taken seriously at the same time. I feel like Roger and Dolly were a couple of artists, and Shel as a writer, who were able to do that, and they’ve had these amazing careers where they’re very successful. Dolly has been someone who has been able to be funny and be taken seriously, but have this persona of being just this kind of blonde, big-boobed woman, but she’s an amazing businesswoman at the end of it. It’s just those really interesting contrasts that I love, that being a little bit of both sides.”

I wanted to talk about Tolman’s There Goes the Neighborhood album because it’s really something. It’s so unique in the sea of country music records out there right now. It’s the ultimate combination of terrific sounding country music, along with some great comedic songs and also some pretty serious stuff as well. One of the tracks is called “Postcard from Jennyville.” Jennyville is a fictional neighborhood filled with interesting characters straight out of the mind of Jenny Tolman. I asked about that and the whole record, giving Tolman the freedom to ramble about the project how ever she wanted.

She began, “Starting out with my now-fiancee Dave Brainard, who is my producer. He’s a Grammy-nominated producer. He produced 12 Stories by Brandy Clark, Jerrod Niemann‘s first couple of records and Jamey Johnson. So, he’s an incredible producer and songwriter. We had met about six years ago now and started writing together at first. There was nothing romantic going on, ” she laughed. “It was purely just writing and working together. So, it was kind of Dave, as we were writing together, who started noticing, like, ‘Hey, there’s these characters that keep coming out in what we’re writing, and what if we actually just kind of made the town and called it Jennyville, where all these characters lived?’ Honestly, right then it was just supposed to be between me and him and our other co-writers. It was just something fun for us to creatively do when we write. It wasn’t necessarily going to be public-facing at all.”

You may have already figured out that Jennyville didn’t stay an inside joke for long. Tolman went on, “So, we started doing that, and as we started creating this little town in our minds, we were like, ‘Wait a second. For me as an artist, this could actually be fun to turn public-facing and get the fans involved in and invite them into this little crazy town that we’re building.’ So, when There Goes the Neighborhood kinda came together, we were like, ‘Okay, well, I guess this is how we’re gonna do it,’ because on the album we’re talking about Jennyville. That was our starting place for building out this whole imaginary town. We really didn’t try to make it a super heavy concept that people had to really pay a lot of attention to, to pay close attention to follow along with. I wanted people to be able to turn it on and enjoy it, and not have to listen in super hard to ‘get it.’ I feel like we did a good job of that because there are tons of little ‘Easter eggs’ hidden all throughout the album.”

Video courtesy of Jenny Tolman and YouTube

It was important to Tolman that the album made sense to listeners without them having to work too hard at it. I agreed that they did a very good job with that because it’s a record that, quite simply, is easy to listen to. It has the perfect mix of songs that will make you laugh, dance, think and maybe even cry. For those that enjoy songs that throw out a lot of fun tidbits for the listener to try and catch, I would suggest “Work It.” One of the funnier tracks on the album, it really shows off Tolman’s comedic abilities while still allowing her musical talent to shine through.

Video courtesy of Hellooo TV and YouTube

We talked about “Work It” and its charismatic leading lady character and Tolman then explained how that song fits into the entire project . “Something important to me, and to Dave as a producer when he’s making a landscape of an album, is what he calls ‘hills and valleys.’ Having those songs that are kind of more like ‘palate cleansers’ to the concept. Something like ‘Love You Too’ or ‘So Pretty.’ Those are definitely a lot more personal to me because I’m not necessarily playing a character in those, whereas a lot of the sassy songs, those are me stepping into a character role. That’s one of my favorite things to do, I love personifying different characters as an entertainer, but having those songs like ‘So Pretty’ and ‘Love You Too,’ where you know those were truly inspired by personal things, that’s important to me as well.”

I highly recommend “So Pretty.” I told Tolman I thought a lot of people could probably relate to the song, but not many would admit it. I guess you’ll need to listen to it to understand what that means. I also mentioned that it really fit the bill as a “palate cleanser.” It’s a track that lets you down and lets you relax for a bit after some of the wilder rides on the record. “So Pretty” was written by Tolman, Mark D. Sanders and Sophie Sanders and is based on a real-life experience Tolman had. To give you a hint about the song, Tolman said, “The wonderful thing about songwriting and co-writing is you can take ugly feelings into the room and make them ‘So Pretty,'”

Video courtesy of Jenny Tolman and YouTube

One of Tolman’s “go to” co-writers is her fiancee Dave Brainard. They write a lot of songs together. I asked Tolman to tell me a little about that. She responded with, “Yeah. Dave and I wrote one song together we haven’t released yet. We’re saving it for something special, but we both think it’s the best song we’ve ever written and that was the first song we ever wrote together. There was nothing romantic about it at all. We just got together as co-writers and yeah, we definitely have a very strong creative connection. Obviously we live together, so it makes it easy to write together when inspiration strikes. It’s also important to me as a writer to have different co-writers, but also I make it a point to at least have one solo written song on the album, so that I can kind of have a complete thought on my own of what expression that I want to say.”

“Love You Too” is the song that Jenny Tolman wrote by herself for There Goes the Neighborhood. This one was inspired by a deeply personal life experience and Tolman shared that with me. “I had just entered into this new relationship with Dave at the time, and we have a 20 year age difference between us. So, it was kind of this, you know, overjoyous time, also a confusing time for me. I was 20 and that was kind of my first time ever not living with my parents. All of a sudden my world had kind of turned upside down in a really wonderful way, but also in a way that I needed to process some things too. When I had problems or insecurities arise, they would come up as body image issues for the most part, in just the way I saw myself, in my own ability to love myself. I noticed that and I just kind of sat down in my apartment one night, and I wrote that song, because I knew that if I couldn’t love myself that I was going to sabotage everything. It was just kind of a note to myself really, if you listen to it, I tried to make this girl sound as awful as could be, someone you would never listen to, someone you would never be friends with. Then it kind of turns itself on its head when in the bridge you realize that that’s you and that’s the way you’ve been talking to yourself. You realize you would never, ever say those things to anybody, you know…”

I continued her sentence by saying, “But there you are doing it to yourself,” to which she replied, “Exactly.” The song has such a good message and we talked for a minute about how it could be so important for young girls especially to hear. They’re loaded with insecurities about themselves, and practicing self-love from a young age is a real step toward leading a mentally and emotionally healthy life.

Video courtesy of Jenny Tolman and YouTube

Next we moved on to Tolman’s own life as young girl and how she started off playing piano and flute. I was interested to know if she transitioned easily to guitar after having played the other two instruments. She laughed and said, “I don’t consider myself to be a guitar player. I consider myself a guitar accompanist. I was really focused on just being able to play the chords that I needed to write my songs with. I consider myself much more of a piano player than a guitar player. If I considered myself a guitar player, it would be an insult to guitar players everywhere. I just got good enough to be able to accompany myself and write songs myself. I was really focused on perfecting my songwriting and focusing more on the performance aspect, and singing and entertaining, and getting the songs right. I leave the actual guitar playing to the professionals.”

Musical talent runs in Tolman’s family. Her dad was a member of the Indian River Boys quartet. They did some impressive things back in the day, including singing on one of country music’s biggest albums, No Fences by Garth Brooks. At the time of this writing, No Fences has been certified 18x platinum. Another fun fact that I needed some more information about was the Indian River Boys were actually put together by Burt Reynolds. It was time to talk about Tolman’s father, Steve Tolman, for a minute.

Image courtesy of garthbrooks.com

I could sense the pride in Tolman’s voice as she spoke about her dad. “Yeah, they were all singing at Burt Reynolds’ dinner theater in Jupiter, Florida back in the day. So, they got to know Burt really well, and Burt became a huge fan of the four of them because they were performing in The Music Man as the barbershop quartet in his theater. That was actually around the time that The Best Little Whorehouse in Texas was coming out, so Burt and Dolly Parton were at the theater one night and they went backstage after the show and were just so excited. Burt was like, ‘You guys have got to stay together for the rest of your lives. I’m gonna call you the Indian River Boys and we’re gonna go make a record. I’m gonna call Snuff Garrett (record producer)’ and all this stuff, which actually happened. They got together and they were together for probably about a decade. Burt was their biggest supporter and made all of these connections for them, and moved them out to LA with him for a while. They also moved to Nashville to pursue the country market and so that’s how I ended up being born here and becoming a country singer. They sang on Garth Brooks’ No Fences album.”

We talked about the enormity of that 1990 record for Garth Brooks and how it still holds up strong today. Tolman shared this, “It’s crazy. So, growing up, I would walk up my bonus room steps to this multi-platinum record plaque that my dad had on the wall. I had no idea who that guy was. You know, it was just kind of the guy on the plaque. Once you grow up and start learning about society a little bit more, you start being, ‘Oh, so my dad’s kind of cool sometimes.'” She followed that with a good laugh.

From a kid that didn’t have a clue who Garth Brooks was to an adult getting engaged in Jackson Hole, Wyoming. That’s the topic we visited next. I was verifying what I’d read online and yes, it was true. That’s where Jenny Tolman and Dave Brainard were engaged. I let her tell me the romantic story.

Photo courtesy of Jenny Tolman

“We got engaged last October. We were out there in Jackson Hole. It was my first time ever playing a show out there and ever being there. I played a show at The Silver Dollar Showroom. I had a sold-out show. It was an amazing weekend. The owner of that venue, his name is Bill Baxter, he’s just an incredible man, an incredible fan, and he put us up for a few extra nights. I guess when Dave heard there was a Jenny Lake Trail, he was like, ‘Aha! Ding, ding, ding!’ We were hiking for about 15 minutes and we came upon this incredible opening at the base of the Grand Tetons where Jenny Lake started, which is the most beautiful thing I have ever seen. That’s where he did it. It was very nicely done.”

The couple returned to Jackson Hole just recently where Tolman played another sold-out show on her own and had the opportunity to open for Runaway June and Midland on separate nights at the Million Dollar Cowboy Bar. They stayed a few extra days so they could plan their wedding which will take place there in March.

Photo courtesy of Jenny Tolman

Photo courtesy of Jenny Tolman

In addition to all of this, during quarantine, Tolman launched her own online cooking show, Hey Good Cookin’, which can be seen on her YouTube channel.

Video courtesy of Jenny Tolman and YouTube

Asked whether she cooked normally or if it was just something she started during the pandemic, Tolman told me she’s been cooking for a long time now. “It’s something that I’ve loved to do for a long time because I’ve had to be gluten-free for over ten years now, way before it was cool and trendy. Back when I was in school and I was kid I had to do it. It was really hard back then to find anything, and my mom actually had to go gluten-free as well with me. So the two of us just kind of learned how to start making things that we couldn’t have anymore, and through that process I really fell in love with baking and cooking. It became just another creative outlet for me because it is a very creative process. It’s just a little bit different than singing, so during quarantine I was like, ‘Well, I can’t play any shows. I’m getting really sick of all these livestream shows. They’re just not the same. What else can I do and be entertaining and keep people engaged?’ Then it was like, ‘Wait a second…’ Everybody was at home and we all have to cook a lot more, so I’m sure there’s people who don’t know what they’re doing at all. I’ve got all these ‘healthy recipes’ to share. Doing a video of them, I get to be a little bit entertaining and put little personality pieces in there. It just became a way for me to almost perform and also be helpful in a way.”

With all of this, you’d think there was absolutely no time left for anything else, but Tolman is also working on her next album right now too. When it will come out is still undecided, but she did give me a few details. “We’re still working on it. So, we’re just starting to put together the new album. The album probably won’t be coming out until early 2022. We may be putting a single or two out before the end of the year. I’m not sure yet. Stand by for more info.”

After listening to Tolman’s There Goes the Neighborhood album and everything else I could find to stream, it was so obvious that she has a tremendous talent for both country music and comedy. I thought the musical ability might have come at least partially by nature. She grew up in a musical family, and was raised in a city soaked in all things country music. What about the comedy side though? Did she feel that was something she was born with or was she influenced by something along the way? Her answer was better than I ever could have imagined.

“Well, it’s funny you ask that question,” she responded with her signature laugh. “My dad actually has managed a comedian named Dick Hardwick for my entire life. He’s actually the one that saw my first steps when my dad was at work. He called my dad because he was watching me. So, I like to say that I was raised by a country singer and a comedian. My bass player, she’s amazing, she’s one of my best friends, her name is Amanda McCoy, she was at a show of Dick’s that we were opening for him. She looked at me during his comedy set and she goes, ‘Your life makes so much sense to me now.'”

We were both laughing hysterically at this and I managed to say she really came up with the best stuff. Either that or I was just asking exactly the right questions. Tolman answered that by saying, “Nobody ever asked me that question before, so I’ve never had to come up with that answer before. It’s funny that I turned out the way that I have, but I guess when you look back on it, it’s really not.”

With just a few minutes left, I asked her about touring. With life opening back up, I was anxious to hear what her road schedule looked like. She was really excited to talk about this. “We’re playing Country Thunder Wisconsin, Country Thunder Florida and opening for Toby Keith out in Reno. We’re going to Pennsylvania and Owensboro, Kentucky. We’re just kinda all over the place the next couple months. In August it kinda slows down for a second, which is good because we’re making a record. September and October starts a little bit back up for the fall. Yeah, we’re rockin’ and rollin’ and it’s just my favorite thing to be out on the road. So, I’m excited to have live music back and touring back.”

Photo courtesy of Country Thunder and Jenny Tolman

There was time for a little fun so I spun the random wheel of cities. Actually it’s just asking Siri on my phone to give me the name of a random US city. I did that five times. I had a list of five random cities and I asked Jenny Tolman if she had ever played in each of those cities. Here’s how that worked out:

Patti McClintic: Charlotte, North Carolina?

Jenny Tolman: I haven’t.

Patti McClintic: Jacksonville, Florida?

Jenny Tolman: I have not.

Patti McClintic: Jersey City, New Jersey?

Jenny Tolman: Definitely not, but that would be a fun one.

Patti McClintic: Fort Worth, Texas?

Jenny Tolman: I have played Fort Worth.

Patti McClintic: Kansas City, Missouri?

Jenny Tolman: I don’t think I’ve actually played in Kansas City. We always drive through there on our route out to Omaha, but I don’t think we’ve actually played there.

The whole point of that little exercise is perhaps the universe is trying to tell the artist they need to book a show in one of those cities they haven’t yet played. It might just turn out to be something great.

I then asked what was something she’d experienced recently, absolutely anything at all, a book she’d read, a movie she’d seen, anything that she would recommend to others? She replied, “Going to Jackson Hole! That one is definitely at the top of my list, but it’s funny you say movies. I just watched The Bridges of Madison County for the first time. I know it’s a really old movie, but it’s got Meryl Streep in it and I was so bawling at the end of that movie. I looked at Dave, because he recommended it, and I was like, ‘What have you done to me?’ It was amazing. I’m always asking everybody, ‘Have you seen this movie?’ They’re all like, ‘Yeah Jenny. It’s super old.’ It was so good.

One more fun question. Did she ever ride a pedal tavern? Her answer was, “I have not. You know, it’s funny. My cousin who’s from Massachusetts, she loves country music and Nashville. I guess it must have been two years ago now, I was playing CMA Fest and she came down for it and she rode a pedal tavern. She was all excited about pedal taverns. So, I feel like I vicariously did a few things through her.”

Last but not least, when Jenny Tolman “Thinks Country,” what does she think? “Storytelling is what country is to me. Going back to kind of how I ended up being a country singer, I specifically remember listening to Brad Paisley‘s song ‘We Danced’ on a ride home from dance class when I was probably like seven. I remember after that song I said to my mom, ‘Mom, I love country music because it’s all stories.’ I have always written stories since I was little. I used to get up and read my stories to the class. So, I thought maybe I’d be a children’s author someday, but it’s always brought me back to country music, so country music to me is storytelling.”

With a quick sense of humor that will keep you laughing and a voice that’s made to sing country music, Jenny Tolman is one to keep firmly on your radar. Her songwriting skills are top-notch too. She strikes the perfect balance of not taking herself too seriously while at the same time navigating a career in the music industry like a true professional. If you listen to her music, you’ll know what I mean. Jenny Tolman is proving even a Nashville native can make it in music here, even with the toughest hometown fan base on the planet.

JENNY TOLMAN can be found:

Website: jennytolman.com | Facebook | Instagram | Twitter | YouTube

Photo courtesy of Jenny Tolman

For more news, interviews, reviews and features that always bring country closer, please visit thinkcountrymusic.com.

*Featured photo courtesy of Jenny Tolman


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