Singer-songwriter Jenny Tolman has long been known for blending humour, heart and honesty into a sound all her own, and her latest single, ‘Maybe Next Month,' may be her most powerful release yet. The emotional ballad — and its moving new video directed by Randy Shaffer — captures the quiet heartbreak and enduring hope of infertility, a topic rarely explored so openly in country music. Since premiering on The Heartland Network, the song has sparked a wave of connection online, with women around the world using the track to share their own stories on TikTok and social media. “This is the most vulnerable song I’ve ever released,” Tolman says, and her unflinching honesty has once again reminded listeners why she’s one of the genre’s most distinctive voices.
With two acclaimed albums — ‘There Goes the Neighborhood' and ‘Married in a Honky Tonk' — Tolman has built an entire musical universe she calls “Jennyville,” where sharp storytelling and southern wit bring her characters to life. Praised by Billboard and Rolling Stone Country for her clever lyricism and authenticity, she’s as much a storyteller as a singer, turning everyday moments into vivid, heartfelt tales. Beyond her music, Tolman continues to champion women in country through her annual Cowgirls at the Cowboy Festival in Jackson Hole, Wyoming, and this fall, she’ll bring her artistry to a national stage as one of twelve contestants on the new CBS series The Road, produced by Blake Shelton and Taylor Sheridan. Whether she’s crafting a poignant ballad or welcoming fans into the world of Jennyville, Jenny Tolman is proving that country music still has plenty of heart — and a few surprises — left to share. We caught up with her to talk all about it.
Hey Jenny, good to talk to you today, many thanks for your time.
Absolutely, I'm excited to talk to you. I'm out here in Jackson Hole, Wyoming, getting ready for the first night of our ‘Cowgirls at the Cowboy' that we do here each year.
Awesome! What a superb bill and set of artists you have this year, right? (Jenny, Willow Avalon, Trannie Anderson, Mae Estes, Ella Langley.)
It's crazy! Oh my gosh, I was literally just having breakfast with Willow and Trannie – it's amazing.
The festival is in its fourth year now. How did you get involved? Tell me about the origins of it all.
The owner of the Million Dollar Cowboy bar is a guy called Bill Baxter. He unfortunately passed away last year but he was instrumental in setting it up. I played out here in Jackson for the first time in October 2020 and he was at the show and became a huge supporter of mine – the festival became his brainchild, he wanted to have the nation's first all-female Country music festival. He called me and said he wanted me to run it and put it together for him.
What a blessing of an opportunity. It's been an incredible four years.
I know all the artists that appear are fantastic but has there been one artist that you, maybe, didn't think you'd be able to get that has appeared on the bill and blown your mind?
Oh my gosh. You know what, Ella Langley being our headliner this year is pretty mind-boggling. In our inaugural year we had Carly Pearce as our headliner, which was pretty cool. She had just won ACM and CMA vocalist of the year too, that was such a huge kick-off for a festival in its first year.
As soon as it's over do you start working on the next year or do you give yourself a break?
Even before it's over! We've already got some offers in the works for next year's line up so we're already working on it! (laughing) You gotta move quick, right!
You've just released ‘Maybe Next Month,' a powerful song about the struggles of infertility. Why did you think it was important to tell this story right now?
Honestly, I didn't even choose to write this song. I woke up in the middle of the night with it completely in my brain, I didn't have to think about it, all I had to do was take my phone and write it down in the notes section! It was kinda like God placed it in my brain and told me to talk about it.
I have a best friend going through IVF right now and it's been four or five years of her trying to conceive and it's been so heartbreaking to walk through it with her. To see how happy she is for other women when they get pregnant whilst holding her own feelings inside is amazing. I wanted to let those women know that they are not alone and that there are women who feel the same way as they might do.
Nobody wants to upset anyone or hurt anybody's feelings or say the wrong thing so a lot of people avoid this subject and it doesn't get talked about. When I started teasing the song on TikTok I felt like it would resonate with a lot of people and it blew up! It was insane to see thousands of women sharing their stories and experiences in the comments. It felt really special – I had no idea what I was doing with it but I decided to be the best steward that I could!
I could see, in this situation, how social media might play a positive role in bonding people together instead of dividing them, which it seems to do most of the time…….
Yeah. I've always seen social media as a blessing and curse – there's a lot of negativity that we all know about but then you get moments like this where you see the community that it can build. I've been trying to dig in and nourish that side of things.
You mentioned about getting inspiration for the song in the middle of the night. Has that happened before?
Never to this level, this is definitely the first song that I didn't have to think very hard to write because it seemed to arrive fully formed. There have been moments of inspiration for a chorus or a verse before but never just a whole thing, all at once!
Something else that is really special is your involvement in the new CBS show ‘The Road.' Tell me about the show and how you came to be involved with it?
Yeah! Oh Gosh. There's 12 of us artists going on tour with Keith Urban and you follow us around every night, getting to know us as people, which is a huge part of the show – it's like a docu-series with a competition element. Hopefully, by finding out the stories of each artist it will help the viewers become connected to us. We get to play original music, which is massive and Gretchen Wilson is out tour manager and Blake Shelton is the host – it's a pinch yourself moment which I was grateful to be a part of.
At the end of last year they reached out to my team and asked if I was available for a zoom call to discuss the show. I interviewed over zoom and then we progressed to call backs in February of this year out in Burbank, California and then the 12 were chosen and then we started filming in March, it was all very quick.
The NDA's that you've all had to sign must be like, water-tight, death level then?
(laughing) Yeah! I keep telling people that it's like I was on ‘The Batchelor.' I know everything that happened but I just can't tell you! It's been a long time to keep secrets I can tell you.
So, somebody who watches and sees ‘Jenny Tolman, the contestant.' What are you hoping they take away from watching you?
I think, for the most part, my story will focus on me being a mom on the road and showing that it is possible to follow your dreams of motherhood and have a career at the same time. It's not always easy but it's worth it and it's possible. I have a great support system around me, which you'll see on the show – they feature my family also.
Musically, I love Country music and I love storytelling with characters. I enjoy making people laugh, I'm a good time! (laughing) When you come to a Jenny Tolman show you are gonna have a good time.
Talking about characters and storytelling – you created the whole ‘Jennyville' concept in which a lot of your songs are set. When did that fictional, cinematic neighbourhood first begin to emerge as an idea for you?
You know, my husband, before he was my husband when we were writing together, we both loved the same style of music. He was a Grammy nominated producer on things like Brandy Clark's '12 Stories' album. We both love female storytelling and as we were writing he brought up things like Dennis Linde's ‘Lindeville' concept and he said ‘what if we created Jennyville? We have all these characters in our songs, we should find a place for them all to live.'
It gave us the space to explore the creative edges and see where it took us with the writing. It gave me this freedom which has carried down through the years with what I write. I also get to say things which are a little ‘outside the box' sometimes or quirky, which is cool.
I really love ‘High Class White Trash' which might fall into that latter category you just mentioned. What is high class white trash as a concept?
I would say it's all explained in the first line of the song. ‘There's nothing like a sample at the bottom of a purse, to cover the Pall Mall reeking from your shirt.' (laughing) I've never smoked but I was inspired by cleaning out my purse one day and finding all these perfume samples in there that I'd had for years! That line came to my head as I thought about the type of woman that would have these in her purse.
It's a little survey of myself mixed in with a little embellishment! (laughing)
You are not afraid to use humour in your music in the same way that Brad Paisley does in his. Songs like ‘World's a Small Town' have cutting lyrics. What things make you laugh outside of music?
My husband! He's really funny. My son is hilarious too. You know what's funny? When I look back at how I grew up – I learned a lot of funny from my dad. He managed comedians and he was the one who I grew up around – he was a singer at Disney World and was very much around the show and theatrical world and then he managed a comedian and so I got a lot of very vivid, humorous storytelling and I look back now and guess that that is where I got it from!
I'm presuming you're working towards a new project now after last year's ‘Broke Down in Jennyville' release. Is that new project set in the same world?
I don't think I will ever, necessarily, shut down Jennyville. It's a continuous place where I will always be creative from. There might be different elements to the next project but it will still be influenced or adjacent to Jennyville.
‘Maybe Next Month' will be part of that project also but I can't say too much more about it right now.
You always have a history of releasing Christmas songs, from ‘Rockin' Around the Christmas Tree' to ‘Mary, Did You Know?' Will there be one this year or will the promo for ‘The Road' and the show itself, which starts October 19, be dominating this year?
I'm not releasing one this year. I'll repost stuff I've done in the past. With the show coming out and the ‘Cowgirls….' festival my brain has been in twenty different places at once!
Is there a Christmas song you've always wanted to record that you haven't got round to doing yet?
Well, we actually hinted at this in ‘Mary, Did You Know?' but I love ‘Oh Come O Come Emmanuel.' That's a beautiful song to sing with a haunting melody, I'd love to do a version of that in the future. Dave, my husband, is so talented. When we were recording ‘Mary, Did You Know?' he ended up combining a little bit of it at the end but I'd love to do a full version.
‘The Road' starts on Sunday 19th October. Find out more here. It will also be streaming on Paramount +
