MUSIC

Hailey Whitters pauses on the road to stardom at Brooklyn Bowl

The 33-year old small-town Iowa native and Nashville singer-songwriter showcases her growing skills as a country artist.

Marcus K. Dowling
Nashville Tennessean
  • The 33-year old Shueyville, Iowa native is a 15-year Nashville veteran finally experiencing greater renown.
  • Her songs like "Ten Year Town" and "Everything She Ain't" spotlight her as one of Music City's finest rising songwriters..
  • 2022 has seen her opening for country music touring favorites like Cody Johnson, Midland and Jon Pardi.

Five of the 20 songs that Hailey Whitters played while headlining a 90-minute set after opener Jordan Fletcher at Nashville's Brooklyn Bowl on Thursday evening were not of her writing. However, the songs by The Chicks, John Denver, Alan Jackson, John Mellencamp and Trisha Yearwood were on acclaimed albums that sold an average of five million copies.

Small-town-born country artists 15 years into life in a ten-year town playing "Wide Open Spaces," "Take Me Home, Country Roads," "Gone Country," "Small Town" and "She's In Love With The Boy" is commonplace in Music City. However, when you're Whitters and it's 2022, it's different.

In this case, they are familiar light posts headed down a metaphorical winding road of story songs that leads to potential superstar success.

33-year old small-town Iowa native and Nashville singer-songwriter Hailey Whitters headlined Nashville's Brooklyn Bowl on October 13, 2022

She played downtown Nashville on a rare "night off" amid celebrating a year that's seen her on the road nearly every weekend, opening for multiple-time country chart-toppers like Cody Johnson, Midland and Jon Pardi. As well she's now a radio-charting artist via ear-worming and the hook-laden pop-country song "Everything She Ain't." Plus, she's added "Grammy-nominated songwriter" to her resume. COVID-19's quarantine saw her pairing with Ruby Amanfu, Brandy Clark, Hillary Lindsey, Lori McKenna and Linda Perry to craft 2021 Song of the Year nominee "A Beautiful Noise," performed by Alicia Keys and Brandi Carlile. Plus, her first headlining gig in Nashville since March 2020 also saw her returning from Shueyville, Iowa -- her hometown of roughly 600 people -- where she married her fiancé, music publishing executive Jake Gear.

Whitters hit the stage at Brooklyn Bowl holding a beer aloft and singing a solo version of her Little Big Town duet "Fillin' My Cup." Her 2020-released album "The Dream" began what has emerged as a prolonged, star-making moment stretching now to nearly three years. For the average aspiring country star, lyrics like "It's all my people sittin' 'round a table / Real sad country on the radio / My go-to blues and my old faithful / Barely pushin' twenty, but still carryin' me home" would be the makings of impressive talent. However, the song's greatest strength is that brevity is at the soul of its wit: a well-developed story of who, what, when, where, why and how is answered in 30 words. Moreover, it's simple enough to be easily heard, remembered and repeated by an audience. Add in a talented band of seasoned players and resonant vocals, and it's a recipe for success.

33-year old small-town Iowa native and Nashville singer-songwriter Hailey Whitters headlined Nashville's Brooklyn Bowl on October 13, 2022

However, 20 minutes later, she played "Janice At The Hotel Bar," a song whose abundant gifts in all the previously-mentioned categories eclipsed the show's opener. The catch? These songs are on the same album -- the one released before 2022's "Raised." Her current album has now captivated tens of thousands of people nationwide, hundreds of millions of people on streaming platforms, plus received critical acclaim everywhere from the New Yorker to the publication for which this review is being published.

If a listener to albums like Ashley McBryde's recently released "Ashley McBryde: Presents Lindeville," Janice -- of slinging drinks from behind the bar at a quaint motel -- feels familiar. After all, she buys her face cream at Walgreens and is a non-smoking fitness-conscious older woman whose language often errs blue, foul and loose. It turns out that Janice -- like McBryde's often fanciful and unquestionably vividly written about -- Lindeville characters, is a real 80-year-old woman who, as the song's hook points out, knows how to "make a good living" and "a good life." When performed in a 1,500-person venue, a song like this feels like everyone's favorite secret spot, exposed to a cadre of good friends who deserve to know it -- and she -- exists.

33-year old small-town Iowa native and Nashville singer-songwriter Hailey Whitters headlined Nashville's Brooklyn Bowl on October 13, 2022

Deeper still, Whitters' set continues and she plays a stripped-down version of her breakout 2020 hit "Ten Year Town." The missing piece to already phenomenal songs emerges at this point: Whitters herself.

In a March 2022 Tennessean interview, Whitters recalled the moment after the success of a song predicated around the idea of cutting deep into how personally impacted she was by the idea of not achieving her goals ("I didn't come this far / To only go this far") left her:

"I was homesick and longing for home. I needed space to sit, think, and have the muse pop out of the sky and just hit me," she adds. "I had to refill my well to inspire myself again. Some may think that's counterproductive, but there I was, spending more time with my friends and family, hearing gossip at my local bar back home, reading books, planting flowers, hiking east of Nashville, and living real life. I couldn't just sit in my room, stare at the wall, and hope a song would jump out from it."

The key to Whitters' finally emerging stardom reaching fruition on top of Billboard's radio charts does not involve making her songs simpler or more pop-appealing. Instead, it's blending who she uniquely is -- as a less melancholy and more bittersweetly positive person -- into a three-minute treatise on the human condition.

33-year old small-town Iowa native and Nashville singer-songwriter Hailey Whitters headlined Nashville's Brooklyn Bowl on October 13, 2022

It wasn't until hearing these songs live, personal, and (somewhat) intimate -- in the way they played in the context of her live show -- that the profound power, and ultimately the massive potential success, of songs like "Raised" album single "Everything She Ain't" could have and why that is the case.

A handclap boosts a hook on the previously-mentioned "Raised" single that, when added to a chorus that states, "I can be the whiskey in your soda, the lime to your Corona / Shotgun in your Tacoma, the Audrey to your Hank / She's got a little style and a Hollywood smile / But believe me, honey, good as money in the bank / I'm everything she is and everything she ain't," it improves and evolves all things previous and current that Whitters -- and her team, plus her live band -- have learned in the past five years, as highlighted through her setlist.

Whitters' first headlining Music City set in 31 months highlighted not just where she is as a person and professional at 33 years old. Instead, it offered a sense of how successful her next 31 months and 33 years could potentially be.

Ironically, they likely represent everything she is and is yet to become.