Hailey Whitters has been asking herself this for a while, spending the last 12 years trying to make it in Nashville. But now, she’s on the fast track to realizing her dreams thanks ironically in part to her song “Ten Year Town,” co-written by Grammy nominee and stellar Nashville songwriter Brandy Clark.
That, coupled with the recent success of her 2020 album The Dream, has the Iowa native gaining traction as not only a songwriter, but artist. She’s written songs for the likes of Alan Jackson and Little Big Town, and she has an impressive catalog of songs she’s kept for herself, too.
She’s a breath of fresh air, really. She’s honest, brash, and eloquent, she has a knack for frank and wise songwriting that cuts to the heart of who she is and where she’s been. If you haven’t heard her name or don’t know her music yet, you need to. She sings about life and love, and ties it all together with a messy bow, wrapped in a little bit of cynicism.
It’s nearly impossible to narrow down her incredible catalog to just a sample, but here’s a small taste of the big bite Hailey Whitters delivers.
1. Ten Year Town
This is one of the most incredible songs I’ve ever heard about the struggle it is to be a struggling artist in Nashville. No surprise that Brandy Clark is a co-writer, the lyrics are incredibly honest about the frustrations that can be generated by following your dreams.
2. Janice At the Hotel Bar
I could never say enough good things about this song. It’s a real-life how-to penned poetically-and it will hit you where it hurts. Janice is a real person, and it comes through quite obviously in the lyrics. We need more Janices in the world… she’s a real badass, and you’ll want to be her best friend once you listen to this song.
3. Living the Dream
Dreams can be defined differently by every single person. They may be simple, like a paycheck at the end of the week, or a one bedroom walk-up apartment. This one’s a Lori McKenna co-write, and it’s well… a dream.
4. People Like You
This song reminds me a lot of Miranda Lambert’s “All Kinds of Kinds.” Hailey wants you to know we all carry things, and that’s okay. Learning to embrace our own problems alongside other people is an important aspect of life. And, if you can learn a lesson along the way, that’s the cherry on top.
5. The Days
The message here is to enjoy every moment of your life. “Don’t count the days, make the days count.” Of course, it’s easier said than done, but Hailey encourages the listener to try and gives a few good reasons why.
6. Get Around
This track finds Hailey rationalizing her pattern of one-night stands and bad decisions. She’s learning how to deal with her demons while being scrutinized by everyone around her. It’s breathtakingly honest as she comes to terms with why she does what she does and internalizes how it truly affects her.
An to ode to growing up in the Heartland, the song reminds you that path you’re on may not be what it’s “supposed” to be, but it’s your dream to chase. And through the highs and the lows, you can always count on going back home to get you back to even.