Hailey Whitters
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Cuts The Deepest: Hailey Whitters

By Thomas Mooney

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"They were all Hail Marys" is how Hailey Whitters describes the five collaborative additions to Living The Dream - the deluxe version of her 2020 breakthrough record that was released earlier this year. "We were so lucky that every person that we asked to collaborate said, 'Hell Yeah! Sounds awesome' - I was fully expecting a no from each of them”.

The Dream found Whitters very much on the cusp of change. It was a culmination of her life up to that point as a struggling yet aspirational songwriter and artist. Full of small-town sketches, late-night letdowns, contemplative daydreams, and rushing anthems, The Dream is the epitome of the life of a young artist. Despite the deluxe edition only possessing an additional five songs and a slight change in title, the weight of progression between them is monumental. "I think of The Dream as a question mark and Living The Dream is an exclamation mark," says Whitters. "It's the end of the chapter and brings my story full circle".

On ‘Ten Year Town’, the centerpiece of The Dream, Whitters notes time and again that she’s “12 years into a ten year town.” It’s easy to focus on the down-and-out demeanor of the dejected ballad, but nestled deep within is a glimmer of hope and an unwavering desire. Whitters is steadfast in her intentions of breaking on through, and that constant aspiration now seems to finally be paying off. The Grand Ole Opry have named Whitters as their Opry NextStage Artist, spotlighting the “most exceptional talent on the forefront of their careers”, an accolade that hints at a great future for Whitters in one of the most esteemed of institutions. While headline tours, award nominations, and the starry spotlight are beginning to surface from her constant will to succeed - the fact she is a brilliant balladeer and storyteller certainly doesn’t hurt.

“Some of these songs are from before my time in Nashville, but they’re the reason that I am here today,” explains Whitters, as she begins to delve into her five favourite songs and records that have inspired her for Cuts The Deepest. “When I first got to Nashville, I learnt very quickly that it’s a songwriter town. I wasn’t listening to records as much - I was going out every night to writer’s nights and hearing live music from these great songwriters.” We could happily put money on Whitters being just as much of an inspiration to new songwriters in the years to come.

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The Chicks - Home

First and foremost, it has to be this record. It came out when I was in high school and I just had it constantly spinning, from top to bottom. That record shaped me as a young girl in Iowa, wanting to move to Nashville to make country music. That's probably the one that lit the spark in that way. The Patty Griffin songs, 'Truth No. 2' and 'Top of the World' are just such great songs. There's a thing as a songwriter where you realize these artists aren't just writing their own songs - but out of all their records, that was the one that I just could not get enough of. That record influenced me so much when I was that age and now look - I packed my bags and moved to Nashville to basically do the same.


Gillian Welch - (Time) The Revelator

That's my get drunk in the bathtub record. It's my spiritual record in a weird way. I put that on and I think it just intrinsically does something to my body and mind, it sends me to this spiritual place. If I'm ever stressed or overwhelmed, I just take a bottle of wine, fill the bathtub and just get drunk in the bathtub while listening. Dave and Gillian are just so brilliant and it just puts me at ease - it's my reset record.

Jason Isbell - Southeastern

I remember when Southeastern came out, I think the first song I heard was ‘Elephant’. That's just "slap you in the face" kind of songwriting. It changed the way I thought about songs. It's so raw, so candid and so real. It’s one of those records where you can feel every word.

Lee Ann Womack - There's More Where That Came From

Solid country gold. Just top to bottom, solid country gold. I remember listening to that record on repeat on a drive from Nashville to Texas once. It’s just such great craftsmanship and country songwriting, with such a simple yet powerful country hook. There are great twists throughout, like on 'I May Hate Myself in the Morning'. Lee Ann also has the country-of-country voices to me, so much so that those songs are going to live forever.

Brent Cobb - Shine On Rainy Day

I'm leaning heavily on songwriting here, but 'Shine On Rainy Day' was, again, another lesson in it. To me, Brent Cobb is the best songwriter of my generation, he's simple but profound. He speaks the common folk language and there's a lot of brilliance in that. My absolute favorite thing about Brent is that he can circle around a thought or topic and make the listener feel as if they're thinking about it for the first time. He’s so great.



Hailey Whitters' latest album, The Dream: Living The Dream, is out now via Pigasus Records / Big Loud Records / Songs & Daughters. Watch the video for 'Fillin' My Cup', featuring Little Big Town, below.