Singer/songwriter Hailey Whitters is coming into her own as an artist. With the release of her first chart single, “Everything She Ain’t,” the Iowa native continues to build momentum with her third album, Raised. After a decade of trying to make a break in Nashville, Whitters had made headway as a songwriter, placing songs with Alan Jackson, Martina McBride and Little Big Town. But cracking open a door in country music as an artist wasn’t happening, as she sang about on her song, “Ten Year Town.” Whitters thought about chucking it all and going back home.
“For the first time in 10 years I was thinking about quitting, and I booked a ticket to the Opry, and I sat as a fan in the audience,” Whitters said. “I remember watching Brandy Clark coming out and performing and just really wanting that still. I knew if I quit now, I would be very disappointed in myself later. I thought…I’m going to make one more record. I’m going to put everything into it. At the very least it can be a cool thing that I put on my shelf some day and show my grandkids. I went in with the mentality of I’m going to make something I love, and I’m going to put everything I have into it, and we’ll see what happens. I think that filled my bowl—making a record for me for whoever needed to listen to it or needed to hear it—that record just changed everything for me. I wouldn’t be here without that record.”
Since then, Whitters has earned her first Grammy nomination as a songwriter and scored her first CMT Music Award nomination for “Breakthrough Video of the Year” (“Fillin’ My Cup” feat. Little Big Town). She hit the road on her debut headline Heartland Tour and traveled the highways and byways with Jon Pardi and Lainey Wilson on his Ain’t Always The Cowboy tour.
We are pleased to feature this new Q&A interview with Hailey Whitters. She talks about trying to fit into Nashville’s music scene, penning songs for her musical idols and the stories behind her single, “Everything She Ain’t” and the Brandi Carlile/Alicia Keys Grammy-nominated song, “A Beautiful Noise” (which she co-wrote).
BC: How did you go about writing “Everything She Ain’t” (with Bryan Simpson and Ryan Tyndell)?
Hailey Whitters: It was our first write back together since the pandemic. We actually were writing a dark spaghetti western vibe, and it felt really dark and moody. We scratched that idea and said, “Let’s write something light…the world feels heavy enough.” Ryan (Tyndell) started playing some of that music. The lines “I’m everything she is and everything she ain’t” jumped out at me. Bryan (Simpson) came out with that first line: “She ain’t a peach you ought to be picking.” We bounced back and forth with some fun quirky lines. We wrote the whole song in an hour-and-a-half. It came together really quick.
Here’s the video of Hailey Whitters’ hit, “Everything She Ain’t.”
BC: I read in another interview that you said, “To me, this song is about being the most authentic version of yourself despite what may or may not be popular at the moment.” Have you been able to remain authentic, or have you had to make some changes to be accepted in the music world?
Whitters: I’ve been in this town for 15 years now. The music has changed a lot since when I first got here. I’ve definitely had a series of tries to be what is popular or what is acceptable on the charts. It took a long time for me to realize that I couldn’t be thinking about all that. I just need to focus on being me and only what I was [musically] and bringing that to the table. I definitely feel like I’ve experienced that. This song to me is like going back to your roots, staying true to who you are, and knowing that you bring something to the table.
BC: To me, your sound gets back to more of the traditional country sound, the way country was earlier on. Was that a hindrance at first?
Whitters: For a long time, what I would hear in town because everything was pop country—I was told often that my rootsy sound was more Americana or more Texas country. I thought it was strange. I just thought I was country. I had people tell me that, and I think it’s quite hilarious because obviously, now we see a lot of those rootsier sounds are making a huge splash in the music scene.
BC: Now you have your latest album, Raised, out, and you’re returning to your roots in Iowa with this one. Why did you decide to go that direction?
Whitters: I wrote a lot of these songs around the time that The Dream record was coming out so a lot of these songs are quite a bit older. I was writing them around the same time I was writing “Ten Year Town.” I think I was very homesick. A lot of my writes were the theme of back home and the Midwest and my family. All these scenes kept popping up. I looked up and I was like…well maybe this is the next chapter. It all really stems from being homesick I guess.
BC: Only so many songs can be released as singles. What songs on the album do you hope people will get a chance to hear?
Here’s the lyric video of Hailey Whitters’ song, “Boys Back Home.”
Whitters: I hope they hear “Boys Back Home.” I hope they hear “Pretty Boy.” Those are two songs that are really special to me.
BC: What is “Pretty Boy” about?
Whitters: It’s a special song about people being who they are unabashedly and unashamedly and being strong to fight the societal norm I guess we place on boys and on gender.
BC: You have a funny one called “The Grassman,” about your grandfather’s farm. Can you tell me about that one?
Whitters: I wrote that song about my grandpa’s sod farm. He sold sod, and everyone in our small town was calling in for pot and thought he was selling grass. He was selling grass, just a different kind of grass. So he made his business motto, at Whitters Turf Farms, “Our Grass is Legal.” I just thought that was hilarious, and I turned that into a song. That song’s about being a hard-working, blue collar grass farmer in the middle of America and reflecting on the lifestyle.
BC: As a songwriter, you were nominated for a Grammy for Song of the Year for “A Beautiful Noise” (performed by Alicia Keys and Brandi Carlile). What did that mean to you, and how did that song come together?
Whitters: That song was such an interesting process. That was the first time I had written a song with that many writers on it. I got approached by Brandy Clark, and she said she had been approached about writing a song for the 100th anniversary of women’s right to vote, and she asked if I’d be interested in writing something with her and Hillary Lindsey, and Lori McKenna. I said, “Absolutely! I’m there.”
It was in the middle of the pandemic, and we wrote a verse/chorus and seeing where it lands. I think Brandy then pitched the idea to Brandi Carlile, and Brandi Carlisle brought Linda Perry, Ruby Amanfu, and Alicia Keys. The song took on a whole life of its own. It was a very interesting thing for me. Typically, you sit down with somebody, and you write from start to finish, and this was kind of a living, breathing song for a while. There were so many different voices on it. I think it’s so cool. We got to watch it on TV one night, and I thought that was pretty dang cool. I thought that was it.
Here’s the lyric video of Hailey Whitters’ song, “Pretty Boy.”
Then a few months later, I got a call from Brandy Clark saying it was nominated for a Grammy. I was like, “Holy Cow!” That’s the thing you dream about as a young singer/songwriter but one of those things that feels like a total shot in the dark. To have that opportunity and to share that moment with all of those women was one of the highlights of my career for sure.
BC: What’s it like writing for yourself as compared to writing for others?
Whitters: I’m really bad at writing for others. I get too inside my head when I think about that. I, honestly, try to write great songs and hope that they land with the people who are meant to sing them.
BC: One of the hit songs you wrote was Little Big Town’s “Happy People.” How did that song develop?
Whitters: I wrote that song with Lori McKenna. It was the first song we had written together. I had that title and thought it was interesting and threw it out to Lori. We gelled on that idea and finished our write that day. I was sitting in a Boston airport, and my publisher called me and said, “Karen Fairchild had already heard it and wanted to put it on hold.” That had never happened to me before. That was a quick turnaround. I’m so proud of that song—I love the positive message that it has.
BC: You’ve also written songs that Alan Jackson (“The Older I Get”) and Martina McBride ““Low All Afternoon” and “The Real Thing”) decided to cut. That must have been a dream come true, considering you were raised on that kind of music.
Whitters: For sure! Martina was the first person to record one of my songs, and she recorded a song that I wrote called “Low All Afternoon.” I had been in town for 6 or 7 years at that point, and I didn’t know if anyone was ever going to record something of mine. So that was a cool feeling to have that happen. The Alan (Jackson) thing was absolutely mind-blowing. I wrote that song with Adam Wright and Sarah Turner. We finished our write that day, and Adam was like, “You know who would love this? Alan Jackson.” He called me the next day and said, “Hey, I sent that song to Alan. He actually wants to record that.” That was so surreal to see someone I grew up idolizing, probably one of my biggest songwriting heroes, to have him sign off and approve of a song that I had written.
Here’s the lyric video of Hailey Whitters’ song, “Raised.”
BC: Finally, you’ll be kicking off the new year with your first headlining tour in support of Raised.
Whitters: I am so excited about that. I haven’t really had an opportunity to play this record top to bottom. I’m excited to get this record out there and to really get to connect with the fans. We did a tour last spring called the Heartland Tour, and we were teasing a few of the songs. It was really cool. It was a good response, but I’m excited to get out there now that the record’s out and they’ve been able to live with it for a while and see what songs are hitting people.
Bill Conger is a freelance writer for various publications including Bluegrass Unlimited, ParentLife, Homecoming, and Singing News and is currently writing a biography on The Osborne Brothers with Bobby Osborne. He can be reached at [email protected].