Over the last few decades, we have learned that country music really is countrywide... or more accurately worldwide. While an overwhelming majority of today's country crop comes by way of the southern region of the U.S., Hailey Whitters has brought a unique flair of midwestern charm to country music since making her first waves in the format in 2020.

Iowa-born and Nashville-based, the rising tunesmith first gained notoriety through her golden pen, notching songwriting credits for the likes of Little Big Town, Marina McBride, Alan Jackson and more. After a decade of grinding it out around town, her breakthrough moment finally came in 2020 with the release of her sophomore album, 

, which found its way onto more than a dozen year-end best of lists. The deluxe edition, 

, saw Whitters commissioning some of her frequent collaborators and friends on five new tracks, including Brent Cobb, Jordan Davis, Trisha Yearwood and Little Big Town, who appeared on the CMT Music Award-winning song 'Fillin' My Cup.'

Following a momentous 2020, the subsequent year took Whitters out on the road with acts like Luke Combs and Midland, as well as saw her notch her first Grammy nomination for Song of the Year for Alicia Keys and Brandi Carlile's 'Beautiful Noise,' written by Whitters with Carlile, Keys, Ruby Amanfu, Brandy Clark, Hillary Lindsey, Lori McKenna and Linda Perry.

Building off her success thus far, Whitters brought everything to a head in March of 2022 as she released her third album, 

, which features her debut single to country radio, 'Everything She Ain't,' as well as the moody heartbreak departed anthem of 'The Neon' and her ode to the guys who taught her some lessons about love and life on 'Boys Back Home.'

Though still in the beginning stages of what will surely be a lengthy career in the left of country Americana space, Whitters has spent the last few years truly honing in on her craft and her sound, all while growing a dedicated fan base and quite a killer catalog along the way.

Home of all the latest news, information and coverage of Hailey Whitters on Holler

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Hailey Whitters has brought a unique flair of midwestern charm to country music since making her first waves in the format in 2020.

Hailey Whitters: News, Songs & Reviews | Holler

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Hailey Whitters is the kind of artist Holler would dream up just to write about.

The Iowa-born, Nashville-based singer-songwriter picked up our coveted 

 which we described at the time as being “a generous and unabashed celebration of growing up in a big family in a small town, that cements 

 as a true country songwriter of note.”

Initially making a name for herself as a songwriter - with cuts for Alan Jackson, Little Big Town and Martina McBride - the crystalline voiced singer-songwriter finally broke through with one of her own when ‘Ten Year Town’ became the surprise breakout country hit of 2019 and made her into the corn star she is today!

Choosing between her songs feels so personal, it’s a bit like picking a favourite child, but nevertheless we’ve done it. Here are Holler’s 15 Best Hailey Whitters songs.

American Gothic with Stephen Wilson Jr.

Black Sheep

The Ride (feat. Jordan Davis)

Heartland

Loose Strings

Beer Tastes Better

Happy People

The Days

In A Field Somewhere

Middle of America (feat. American Aquarium)

How Far Can It Go (feat. Trisha Yearwood)

One More Hell

Janice at the Hotel Bar

Everything She Ain't

Ten Year Town

Subscribe and listen to Holler's Best Hailey Whitters Songs Playlist Below:

A list of the 15 best Hailey Whitters songs, according to Holler.

The Best Hailey Whitters Songs

15 of the best songs from the country music's very own corn star

Hailey Whitters: A List of 15 of the Best | Holler

They say it takes a decade to make a name for yourself in Nashville. After closing in on the milestone without the artistic trajectory she’d hoped for, Iowa-hailing singer-songwriter Hailey Whitters started to question her fate. Though the 31-year-old’s pursuits of becoming a country star were certainly never idle – she’s racked up numerous song-writing credits for artists including Alan Jackson, Martina McBride and Little Big Town – something wasn’t quite clicking. Stepping back from the daily grind, Whitters realised that instead of waiting for Nashville to write her story, she had to write it herself. It was then that she became the fearless songwriter she is today – bold, inspired and truly independent. 

What inspired you to make the move to Nashville?

I come from a town in Iowa of about 600 people. It's very small, everybody knows everybody - we don't even have a stoplight! Growing up I always had this really odd inkling that I wanted to make country music, and I think that probably stemmed from having country radio as one of the only sources of music. I just grew up with my ear to the radio, and to a lot of the 90's country icons: Alan Jackson, Lee Ann Womack, Trisha Yearwood. I was hellbent on figuring out how to be in country music someday.

When I was in elementary school, I asked my guidance counsellor how you become a country music singer, and he told me that a lot of country music singers write their own songs. So I thought, "Ok, well, I'm going to start writing songs then". I got a guitar, I started learning a few chords, putting a few things together, then when I was 15, my mom brought me down to Nashville and just unveiled this whole new world to me. I remember we went on a tour of the Opry and the curtain went up, and it was just like, "This is what I want to do for the rest of my life" - that was the moment that I just knew. As soon as I graduated high school I moved to Nashville, and I've been here now for 13 years.

16 is such a young age! Was it a warm welcome to Nashville, or did you have to fend for yourself until you found the right people? 

It's incredibly young! I'm a pretty strong-headed person and it served me well in this case. I owe a lot of credit to my parents because they really supported and encouraged me. It was interesting though, because I didn't know a single soul. So not only was I moving away from my entire family and friends, but I was also moving to a brand-new city - and I'd never even been to a city at all. I just started knocking on doors – I’d go down to Broadway and walk into the honky-tonks and ask the club owners for a show. MySpace was a thing then too, so I got on there and started messaging songwriters, venues and anyone I possibly could co-write with. I learnt very quickly that Nashville is a co-writing town, and I knew I needed to meet people, so I really just started asking anyone who would listen if we could collaborate. Nashville is a very friendly community, but it is also very hard to break into that industry for a while - it's very tight, but once you can get an in, you're in. But it did take me several years to get an in. I was just spending a lot of time honing my craft and trying to write some songs before I had those meetings.

Initially, was your time in Nashville more dedicated to writing than performing?

Absolutely. I thought that if I could write great songs then that was what would grab people's attention first, so that was the focus. I don't know if that came from looking around and seeing that all my favourite artists were songwriters first. I was looking at Eric Church and Miranda (Lambert) and some of these Americana artists - everyone was writing their songs, so I thought I had to have a good handful of my own songs before I could really pursue the artist thing.

You’ve had some experiences of going to record label meetings in Nashville and experiencing sexism and misogyny. It's also a common theme in your lyrics?

Yeah, it's the strangest thing. I don't know what it's about - I kind of wish they would just come out and tell me. I was taking a lot of meetings - I wasn't seeking them out, they were coming to me - and I just felt like a show pony. I went in, put on the dress, played a few songs, and then it was like this weird stalemate. I remember I was in one and the label head was saying all these dirty jokes and shit. I guess that's his humour, and I can roll with some dirty jokes, but I just didn't feel like I was being taken seriously. But you see things they are signing, Instagram influencers and shit getting record deals, and then it started to make sense. I was like, "Ok, they're not really interested in great song-writing or great artistry, they just want what is already famous". That's not what I'm interested in. I'm interested in creating art that is going to last, art that is going to move people. It's not like I'm some art snob, I'm just trying to create great music. You know, great music - the music that I grew up on, the music that told a story, the music that I was moved by when I was just a small-town girl in Iowa listening to the radio, hearing songs like 'Red Rag Top' or 'Remember When'. I felt those songs in my core, and it clicked something in me. That's what I'm trying to make, that's what I thought Nashville was about and that's what I came here for. 

Are there any other kind of troubling systems or attitudes still in place in Nashville?

I don't think so. I'm not trying to dog on anyone for doing what they feel like they have to do to keep their job, but that sort of toxicity and mindset was just completely uninspiring and deflating to me. That's why I stopped taking those meetings, and why I was so relieved to find Big Loud, who are so open-minded about the industry. It might be a generational thing, the mentality of those who were used to making 20 bucks on a CD in the 90's, but it’s just not the reality of the industry anymore. It requires open-mindedness and new innovative ideas. I see Nashville starting to adapt to that a little bit more. That's cool to me. There’s a lot of positive growth and change that's happening in Nashville.

What's your favourite thing about Nashville?

My favourite thing would probably be that it's all about the song. Everyone says Nashville's a song town. I want to preserve that - that's the reason people come to Nashville. You can come to Nashville and still hear a song, just a guitar melody, that will melt you. I think that that's something that maybe gets lost a little bit as Nashville becomes more modernised in its production, but I think if you strip it back to a guitar, vocal, a set of words and a melody, it's as simple as that. It's something that's desperately worth preserving in this town, because we have some of the best songwriters in the world, and it makes me sad to see ones that are getting different jobs or leaving the town altogether. Nashville was built on songs, and I hope that there are people in charge that are preserving their power.

Hailey Whitters' latest album 'The Dream' is out now via Pigasus Records (Big Loud / Songs & Daughters).

They say it takes a decade to make a name for yourself in Nashville, Hailey Whitters shares her journey.

Ten Year Town: Hailey Whitters

Stepping back from the daily grind, Whitters realised that instead of waiting for Nashville to write her story, she had to write it herself.

Hailey Whitters: Ten Year Town | Holler

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Album - Hailey Whitters - Raised

While Hailey Whitters now calls Nashville home, her idea of country is the Midwest - its grass fields and farmers, warm beer and whiskey, apple pie and porch lights. After the breakthrough success of her forward-focused 2020 debut 

 she was able to take stock of how far she’d come from humble beginnings in Shueyville, Iowa, population 731.

a generous and unabashed celebration of growing up in a big family in a small town, that cements Whitters as a true country songwriter of note.

With an emotive voice that can toggle between plaintive and sassy, tenderness and twang, she covers a lot of terrain while keeping her focus hyper-local (the album is bookended by ’Ad Astra Per Alas Porci,’ translated as "to the stars on the wings of a pig”). It’s clear this is an album of the old-school variety, with considered sequencing, preludes and interludes and even a snippet of spoken word. 

The title track — a wistful recollection of how Whitters’ upbringing shaped her heart — is also the lead-off tune, immediately establishing the theme. Gilded with pedal steel and evocative details such as Pampas grass, Sunday dresses and “a little dirt don’t hurt”, the song is both an homage to place and a declaration of being in it for the long haul.

Pride of place translates to self-respect, and Whitters does double duty as both an every woman and one-of-a-kind-find on ‘Everything She Ain’t', the cheeky lead single she released earlier this year. Complete with handclaps, fiddle and banjo, Whitters and co-writers Bryan Simpson and Ryan Tyndell elevate several tropes with their clever wordplay and skilful phrasing; “Honey there's plenty of fish in the sea / But if you take a second look / you'll see there's only one of me”.

It's Whitters’ specificity of detail and willingness to embrace contradictions that give her songs weight. You can’t help but think of another ode to the American Heartland, John Mellencamp’s ‘Jack and Diane’ (another artist from a small town, albeit not as small as Whitters), when listening to ‘Middle of America,’ especially with the addition of BJ Barham of American Aquarium’s vocals. It’s a winning duet, where Whitters balances her contrasting considerations within her witty one-liners; “between going nowhere and going crazy / raising hell and raising babies”.

is full of Whitters’ heart, nowhere more so than on ‘Big Family’. With its husbands and cousins, ex-wives and living-room preachers, Whitters sings of the invaluable lessons that only come with learning to live with others, even when it's messy. It’s a welcome tonic in an age when families are often more divided than not.

Even as Whitters plants her feet ever more firmly on the ground on 

detailing her ordinary origins through the lens of finding success, her music is reaching the stars.

Hailey Whitters new album, Raised, is out Friday March 18th via Pigasus Records / Songs & Daughters / Big Loud. You can purchase the record from one of Holler's selected partners below: 

A review of Raised, the latest album by Hailey Whitters, released via Pigasus Records, Songs of Daughters & Big Loud Records.

Hailey Whitters - Raised

Raised is a generous and unabashed celebration of growing up in a big family in a small town that cements Whitters as a true country songwriter of note.

is a generous and unabashed celebration of growing up in a big family in a small town that cements Whitters as a true country songwriter of note.

Hailey Whitters - Raised Album Review | Holler

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The run of shows will take Aldean across Oklahoma, New York, Virginia and more.

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It's the natural synergy Whitters has with the Scottsdale crowd that wins over those in attendance at Dreamy Draw Festival.

Hailey Whitters' Cornstar Country Reigns Supreme at Dreamy Draw Festival 2023

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The ‘Everything She Ain't’ hitmaker is up for 2023 New Artist of the Year.

Hailey Whitters Earns First Ever CMA Awards 2023 Nomination

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