Jenny Tolman: 5 Songs That Shaped the Songwriter

by Jim Casey

I’ve said it once, and I’ll say it again: singer/songwriter Jenny Tolman is one of Nashville’s hidden gems. Her 2019 debut album, There Goes the Neighborhood, was among the best albums of the year. The Music City native brought her fictional town of Jennyville to life with songs like the title track and “High Class White Trash.”

As Jenny gears up for her sophomore project (more on that down the road), she is releasing new song, “I Know Some Cowboys,” on October 22.

“‘I Know Some Cowboys’ is a song that was born out of my very first tour throughout Texas,” said Jenny to Outsider. “Everywhere I went, there would be cowboys opening the doors for me, carrying my gear, tipping their hats—on and on. They would try to teach me how to Texas two-step—which I was horrible at—but it was so much fun. So, when I came home, I said to my sweetheart/producer, Dave Brainard, ‘Honey, you better step it up! ’Cause I know some cowboys!’ And we always love to laugh and be able to poke fun at each other like that, so we ended up writing this song with our dear friend, Bill Whyte. It’s always a crowd favorite on the road. And a personal favorite of mine, because I like to show that girls can play honky-tonk songs too.”

As we eagerly await Jenny’s new single, we got her to sit down with Outsider to talk about the 5 Songs That Shaped the Songwriter.

1. ‘We Danced’ – Brad Paisley

Jenny Tolman: I first heard this song on the radio while my mom was driving me home from dance class, when I was probably five or six. It’s my earliest memory of actually listening and understanding lyrics to a song. I remember how I could literally see the movie in my head of everything that was happening in this song. I told my mom once it ended, “Mom, I love country music because it tells stories.” Ever since then, I’ve been obsessed with telling stories through country music.

2. ‘The Fool’ – Lee Ann Womack

Jenny Tolman: I love songs that are a woman-to-woman narrative, like this one. I think some of the most overwhelming emotions that can be related to are jealousy and insecurity of some type, when it comes to women comparing themselves, or their love. This song is one that does it so well, because it not only has that powerful narrative, but it also turns it on its head and the singer points the finger at herself for being the “fool.” I find these uncomfortably relatable, complex storylines super intriguing.

3. ‘Still Gonna Die’ – The Old Dogs

Jenny Tolman: Shel Silverstein is my favorite writer of all time. So, it only makes sense that he is on this list with “Still Gonna Die.” I have always loved humor in country music, but better yet, humor that delivers a deeper, more meaningful message. This song is one that is chocked full of potentially dark comedy and laughs, but also good intentions on living your life to the fullest. I have learned a lot from studying the way Shel crafted songs to be so diverse and wacky, yet so simple and relatable. And this is one of my favorite examples. Plus, I end every show of mine with this tune.

4. ‘Bible on the Dash’ – Corb Lund

Jenny Tolman: Corb Lund has some of the coolest, most unique lyrics of any current writer that I’m aware of. This song has such a fun storyline to follow, and it’s like nothing you’ve ever heard before. I love songs like this that continue to inspire me to come up with cool ideas that nobody else has ever sung about. 

5. ‘Love Is a Losing Game’ – Amy Winehouse

Jenny Tolman: I’m a big fan of Amy Winehouse’s music in general, but this particular song I just think is so simple and heartbreaking, that everyone who listens to it just has to stop and close their eyes for a moment. I think we have all felt this way at one time in our lives. And to hear it in such a raw delivery is breathtaking to me. Amy’s writing definitely taught me to not be afraid to say exactly what you think—especially if you listen to her full body of work.