Listen Now: Hailey Whitters, Nashville’s Next Big Star

The songwriter behind “Happy People” has plenty more hits up her sleeve—and her forthcoming album, The Dream, is ample proof

Photo: Harper Smith

Hailey Whitters in Watkins, Iowa.

“Everyone always says Nashville is a ten-year town,” says singer-songwriter Hailey Whitters. “That’s how long it takes to get your break.” Whitters should know. After arriving in Nashville in 2007, the sharp-witted Iowa native played whatever stage she could, from downtown honky-tonks to a regular shift at the airport. She wrote constantly, eventually inking a songwriting deal and penning tracks for the likes of Martina McBride and Alan Jackson. But it wasn’t always easy to recognize her own forward momentum. “In my tenth year here, I was questioning a lot of things,” she says. “Am I supposed to be here still? Have I put in my dues? Can I say I tried and go home?”

It’s a good thing she didn’t. Out this month is Whitters’s new album, The Dream, which opens with the track “Ten Year Town.” The song’s self-deprecating humor and ultimately hopeful message make an apt primer for the album, a meditation on both chasing dreams and finding the joy in life’s smaller moments. 

“Happy People,” which Garden & Gun is proud to premiere below, is an ode to the stuff that breeds real contentment: giving to others, cutting people a little slack, and not letting failures get you down. Co-written with Lori McKenna, it became the first of Whitters’s work to hit country radio when Little Big Town recorded it in 2017. “The idea came from a day at a park in the middle of downtown Boston,” Whitters says of the song. “In the bustling city, it was a quiet, serene playground where everyone was just enjoying each other’s company.” She took the idea to McKenna, and as the two began working on it, the song came together quickly. Its success was just as swift. “I hadn’t even left the Boston airport, and I got a phone call that Little Big Town had put it on hold,” she says. “It was a song of so many firsts for me, and I’m really proud of it. I think the message is something that we can always afford to hear.” 

Whitters’s take on it showcases her no-frills vocals—and brings a little more twang. Listen to the song below, and read more from our interview with Whitters, including how Dolly Parton inspired her to keep going and why it’s the little things that make life sing. 

The Dream will be released on February 28 and is available for pre-order here.

Tell me about where you grew up. How did it lead you to music?

I am from a small town in Iowa—grew up in the middle of a cornfield. [Laughs] I come from a very blue-collar family—this giant Catholic family—and no one is musical. But I do think they’re very creative. My grandma used to sing me Irish songs that her dad used to sing to her, and she was a great painter. There wasn’t a huge music scene where I’m from, so I grew up mostly listening to country radio and a lot of the women of the ’90s: Trisha, Patty Loveless, Martina, Lee Ann Womack. I started writing songs when I was 15 or 16, and then started playing random places in my hometown. I played, like, a sushi bar in Cedar Rapids, sports bars, anywhere that would give me a spot. I moved to Nashville right after I graduated high school. I didn’t know a soul.

In addition to “Happy People,” you also wrote the track “Janice at the Hotel Bar” with Lori McKenna. What inspired that song?

The real Janice, who is well and kickin’ up in New York City right now, was the inspiration for a lot of those lines. But we started pulling advice from women who we’ve come across, or women who were important figures in our lives and had changed us. There is a 95-year-old woman in my hometown who still mows her own lawn. She has the best Christmas light display of anyone, and she puts it all up herself. And then my grandma always told me a glass of red wine each day is good for the heart. The hook, “Go on and make a good livin’, but don’t forget to make a good life,” was just something I needed to hear. The year I was making this record, I was feeling really broken, really low. I’d spent ten years, twelve years, chasing this one particular dream, and I didn’t know if it was ever going to happen. I was thinking, Hey, this may not work for you, so you need to make sure you’re living a great life outside of this one thing that you’ve been putting all your energy into. It took me back into being intentional, making sure that I wasn’t missing out on all this life outside of chasing this one dream. 

The album takes its name from the song “Living the Dream,” which lists a lot of things people might find not so dreamy— tiny apartments, small talk, post-break-up smokes. 

You know, everyone always says, “Being in Nashville, being in country music, oh you’re livin’ the dream.” And there’s a lot that wouldn’t necessarily be considered positive. I was at this point in my life when I had been trying really hard to be intentional with my time and with my energy. After having been desensitized for so long, I was regaining feeling—now with a deeper, fuller understanding of the preciousness of life. All of a sudden, the most mundane and common occurrences felt grand. I wanted to celebrate the positive and negative because both shape who we are. On the most fundamental level, I wanted to say, “I’m glad to be here.”  

You said the women of ‘90s country led you to music. Who is inspiring you right now? 

When I was feeling really stunted with my writing a while ago, I started going through Dolly Parton’s catalog, top to bottom. I know: Everyone’s obsessed with Dolly. But I’ve been listening chronologically, which takes a while because there were times when she would put out five records a year. Doing that taught me that you can’t really negate what is or isn’t worthy of a song. She wasn’t holding anything back. She was bold. She covered a lot of different topics, including some really dark topics, and she made it look effortless. She inspired me to just write what I was feeling and what I was seeing—to never think, “Well, this isn’t gonna be a hit.” Because you just never know.