Hailey Whitters: From Songwriter To Star

Hailey Whitters’ “Everything She Ain’t” already has more than 34 million streams on Spotify. Before she launched her own career, she wrote songs for Little Big Town, Alan Jackson and more. This summer, Whitters set out on her first-ever headlining tour, “The Heartland,” and Jon Pardi’s “Ain’t Always The Cowboy Tour,” – all success she attributes to “Everything She Ain’t.” 

“We just wrapped the Jon Pardi tour and we’re about to go out with Cody Johnson,” Whitters tells Pollstar. “I will say next year is looking pretty stacked with festivals. I think that’s a good sign and a result of the song doing well.” 

The track became one of Whitters’ first songs to land on the Billboard charts, peaking at No. 3 on the all-genre Bubbling Under chart. “Everything She Ain’t” has proven to be her career catalyst, catching the eye of other musicians and expanding her fanbase.

“Her most recent [headline dates] were in the spring,” Whitters’ agent, Justin Cahill at CAA, tells Pollstar. “So we had a run in February, March and April. I think for the most part, they exceeded everyone’s expectations. She did two sold-out nights in her hometown in Iowa, which is 1,500 in a town that has a population of 800. That’s a pretty good ratio. And the second half of the tour on the West Coast was incredible.”

While the success of “Everything She Ain’t” has propelled Whitters’ career, it was her prior experience as a songwriter that allowed her to foster relationships with various artists. In 2020, she joined Alicia Keys and Brandi Carlile on the Grammy-nominated “A Beautiful Noise,” which is competing in the Song of the Year category. Whitters joined seven other songwriters for the single, which works to encourage more women to get out and vote.

“The wonderful thing about Hailey is that artists love her,” Cahill says. “And so we had a lot of really incredible support opportunities starting with Maren Morris at the end of 2019, because Maren heard ‘Ten Year Town’ and fell in love like the rest of us did. She had her out when no one knew who she was. And going into Midland at the end of last year for about three months, and Jon Pardi this entire summer. I think we’ve just been lucky to have some really strong support that I think suits Hailey’s style. We’ve been taking those rather than putting a ton of headline stuff on sale. But we’re working on some headline shows in the future.” 

Whitters has been in the Nashville scene for years, moving to the city at only 17-years-old. Whitters laughs and calls herself naive at the time, saying, “I think I was just young and dumb enough to go for it and chase it.” Now, 15 years after moving nine hours away from the rest of her family with a vision of her name in lights, her dreams came true. 

Whitters and managers Matt Graham and Chris Kappy have been working together the past three years, with Graham emphasizing how she’s grown as an artist in that time. 

“She started as maybe a little more reserved and still finding her voice on stage, getting her breathing techniques right,” Graham says. “It’s a big difference cutting in the studio and performing for a live audience, moving around the stage and being able to make sure you can vocalize your songs in the way they sound in the studio. Now, she’s really just come into her own as this incredibly dynamic performer that can work the entire stage. She’s figured out her breathing, she’s really mastered her own voice. It sounds like the records when she’s out there. She’s the consummate female entertainer who knows how to work the crowd, move a little bit, connect with her band on stage and with her audience. It doesn’t matter if she’s headlining or opening, she just seems to get tremendous applause and adoration and long lines at the merch booth.”

Whitters still finds it surreal to reflect on all she has achieved in the years since. She thrives in midwest markets. Her agent, Cahill, speaks of how for 10 years before she hit the stage, she had been one of his favorite songwriters in Nashville. 

“Hailey’s everything you look for in an entertainer,” her manager, Graham, says. “There’s pageantry, there’s incredible songs, there’s incredible musicianship. Her music transports you to the place she grew up in the midwest, it’s so her landscape both visually and sonically.”

Whitters’ first headlining tour took place last spring, with the “Heartland Tour” honoring her hometown and proving her chops in live music. As she looks forward to what comes next, she’s leaving her heart open.