Hailey Whitters

First Published March 2022


RAISED, Hailey’s new album, drops on March 18th.

“I am so excited to come to Ireland. My grandma was very, very Irish, her maiden name was Callaghan and we’d been tryin’ to plan a trip to come over there. But I’m very excited that I get to come over next month.” 

That was the voice of HAILEY WHITTERS, who – for my money – is one of the most exciting artists to hit the American country music scene in the last decade. Easy. If she’s a new name to anyone out there, get used to hearing a lot more about her, and do yourself a favour as soon as you’ve finished reading our chat, go look her up, get her music, and follow her everywhere you can. That’ll be a decision that will bring only happiness – in the shape of some damn fine country music – to the rest of your days. And if there’s anything we all need right now, then God knows it’s as much happiness as we can lay our hands on…

Earlier this month, on the afternoon I had the pleasure of meeting Hailey for the first time, there was less than a month to go before she’s due to take to the 3Arena stage in Dublin to perform at this year’s C2C – Country-to-Country – festival. And as you read this for the first time, the evening of Saturday, March 12th, has drawn even closer. So, that’s where we kicked things off: How is Hailey feeling about finally making it over here to see us? 

“I…am…over the moon! It feels like it’s been a long time comin’, ya know. But I can’t believe it’s finally here!” 

Hailey, born and raised in Iowa, comes from an Irish Catholic background. Both her parents were one of nine children, one of her grandfathers was one of fifteen, and Hailey herself is one of six. I wondered if, by any chance, she knew much about her Irish heritage? Was there any family history that had been passed down through the years? 

“Ya know, I don’t, and it’s one of my biggest regrets that I haven’t got to know more about that. My grandma, her maiden name was Callaghan, and I never got to meet her dad. His family, I think, came from Ireland and were in St. Louis before moving to Hiawatha. I wish I would have got to meet him. I wish I would have got to know so much about it. We were tryin’ to plan a trip before she passed actually, and I would have loved to have gone with her. I would have really tried to dig in there and learn more about where we came from and stuff. But I don’t [know much], unfortunately. I wish I knew more. I have one song – and I don’t know if it’s Irish, it may not be – but it’s a song that her dad used to sing to her, and that she used to sing to me. That’s kind of like the biggest thing I got from him, having never got to meet him.” 

Does Hailey know what that song is called? 

“[Laughs], It’s such a silly song, and I don’t know what it’s called. It goes like, ‘Don’t ever marry an old man/ For an old man, he is…”, ya know, it was about not marrying an old man! Marry a young man! [Laughs]. Does that sound Irish? Do you know that song? [Laughs]. It was great.” 

I didn’t know the song, but I admitted that it sounded like it could well be one of ours! 

Hailey’s trip to Ireland for C2C isn’t the only reason why March is going to be a huge month for the rising star. On March 18th, her brand new album RAISED, officially comes into the world. A seventeen-track collection, with latest single Everything She Ain’t (if you love The Chicks from back in their Dixie days, you’ll dig this too!) already here to enjoy, I wondered if Hailey could give her fans a little heads-up on what else we can expect? 

“This record feels like the prequel to ‘The Dream’ (Hailey’s debut album). If ‘The Dream’ is the girl who moved to Nashville to chase her country music dreams and never give up, ‘Raised’ feels like the why, ya know? What inspired her to do that? What encouraged her to do that? It’s very much a celebration of where I come from, conceptually but also musically. You can hear a lot of the musical influences that were influencing me back growing up as a kid in Iowa listening to country radio. The Chicks, Alan Jackson, so there’s fiddle and steel everywhere on the record. It feels very country, yeah!” 

I love finding out why someone gives a body of work the particular title that it ends up with, because there can be so many possible choices. So why Raised for Hailey on this occasion? 

Well ya know, once the songs [for the album] started coming in, it started to seem very much just about where I came from. About my hometown and growing up in the midwest, in the heartland. So I think that title, well we’d had the song called ‘Raised’ and it’s really about how I grew up, my childhood, what I grew up listening to from a production standpoint, the songs that were raising me, ya know, that I was being influenced by and that were inspiring me to pursue country music.” 

Moving on to talk about Hailey as a songwriter, in other interviews I’ve heard her do, Hailey has referenced people like Alan Jackson, Tim McGraw, and Matraca Berg when it comes to the importance of storytelling and lyrics in songwriting, and how she used to actually study Lori McKenna‘s records. When Hailey does something like that, what – as a songwriter herself – is she listening for? What’s moving her in a song? 

“Well I’m always pretty drawn in lyrically. I tend to try and pay a lot of attention to the lyrics. That’s usually what’s kind of like the sucker-punch to my heart, a really good lyric. And I’m kind of a sucker for the old-school country hook. The play on words there is always what draws me in. Just recently there I was listening to ‘Nobody In His Right Mind Would Have Left Her’, the George Strait song, so clever. And just plain-spoken. Again, where I come from. I always say about my dad, for a man of few words he sure says a lot! It’s that kind of lyricism that I’m always drawn to in country, not all these fancy, eloquent words. It’s just plain-spoken, very simple, but it can twist in a way that has a lot of depth and a lot of meaning. That’s what’s always drawn me to country music.” 

So would it be fair to say that with her own lyrics, Hailey probably spends a lot of time trying to make them sound as simple as she can? Even though that doesn’t always come straight away, sometimes you have to really work at paring things down.

“Yeah, totally! I mean, to be able to say things in a very conversational manner is what I’m always trying to do in my own lyrics.” 

Hailey released The Dream on her own label. And what I think I love even more than that fact, is that she called her label Pigasus Records, inspired by a John Steinbeck quote…

“Yeah, John Steinbeck is just one of my absolute favourite authors. I’m just so moved by so many of his books, he’s been a big inspiration for me, writing-wise. I remember reading an article where he had said that in his signature or something, ‘To the stars on the wings of a pig!’ That kind of became like his stamp. I thought that was interesting, the midwest connection with Iowa being the biggest pork producer, and my aunt had a pig farm growing up. So it’s about those humble beginnings for me, and the element of doing the impossible. Because it was so difficult for me to get anyone to take me seriously in Nashville. So it felt like a little of that ‘when pigs fly’ mentality, where I’m going to do it no matter what. So if you’re not gonna sign me, I’m gonna start my own label, and I’m gonna do it anyways! Pigasus has become a very big symbol for me too, not only of where I come from, but of me trying to make my place in this business, and this genre.” 

Hailey has mentioned before how a fellow songwriter, one more experienced at the time in the ways of Nashville, advised her to find a place that would help keep her grounded. Not in the sense that she might get too big for boots, far from it, but rather in the sense of finding somewhere that she could always depend on to give her a firm connection to real-life, away from the ‘show’ and ‘business’ sides of life in Music City. And her hometown of Shueyville is very important to Hailey in that regard. But in terms of other advice that may have come her way as a songwriter, I wondered if there’s been anything that’s been shared with her and has had such an effect or an impact that it’s become something she tends to pass onto other songwriters now as well? 

“Yeah. I feel that recently one that’s been relative in my writing, and not only in my writing but in my industry, is just writing for your fanbase. It sounds like, d’oh, ya know, you should be doing that no matter what [laughs]. But yeah, really just focusing on your fans, and serving your fans in your writing and in your songs and your records. I think it’s easy sometimes to look around at what everyone else is doing and trying to compare and be like them, or trying to fit industry standards. But really [it’s about], just remembering who’s buying the ticket to come to your show? Who’s buying your records? Sing for them. Write for them. Make records for them. Because they’re the ones that allow you to be able to do it in the first place. And they want to hear what you have to say, and they want to hear you sing for them. You just have to really stay focused there. Don’t focus about radio, don’t focus about all of the other things. Focus on your fans.” 

EVERYTHING SHE AIN’T is the lead-off single from Hailey’s new album, RAISED.

Just moving away from the music side of things for a moment, because for Hailey and her producer and boyfriend Jake Gear, music isn’t the only reason why 2022 is going to be an extremely memorable year. The pair are getting married! How are plans going in that regard, especially with so much else happening in Hailey’s career at the same time? 

“Yeah, we’re getting married! [Laughs]. We’re planning things, but ya know, my wedding planner probably hates me because I’m on tour, I’m about to release a record… [laughs]. The wedding is like the third priority in my mind, so I guess I’m probably not the best bride in that respect, ya know what I mean! [Laughs]. But Jake is cool about it, he gets it, and he’s right there with me. We’re just so excited about this record. We’re excited to get married, too! [Laughs]. It’s probably going to be a little bit more low-key for us, but that’s the way we’d want it anyway, just getting a bunch of our best friends and our closest family members in a field together and everyone just getting drunk, that’s the M.O. for our wedding [laughs]. We’re thinking October, we kind of always envisioned a fall wedding.” 

On August 7th in 2019, Hailey made her debut at the Grand Ol Opry, singing two songs on that night. Just before she walked out on stage, as she waited in the wings, the Opry’s GM Sally Williams advised her to take a moment to “soak it up”, because it would fly by. I asked Hailey if there have been other moments in her career since then when those words have echoed in her mind and she’s thought to herself, “I really need to enjoy this, to take this all in as it’s happening and not just let it pass me by…”

“Yeah, I think when I played the Ryman [Auditorium] in December, I think 10th and 11th last year, it hit me there, too. Because that’s just such a bucket-list play for me, to get to play the Ryman. When anyone would ask me what’s the ultimate venue that I’d love to play in, it was the Ryman. So I remembered Sally’s advice then to just soak it in. And anytime I’m really feeling nervous, to be honest…which is a lot of times [laughs], before I go on-stage. Just remembering that advice has been so helpful because I am just so lucky to get to be here and to play those stages, ya know. So, amidst the nerves, I’m trying to remember to…breathe, look around, soak it up, as much as possible.” 

Does Hailey have any little tricks or rituals that she goes through before she goes on-stage, as so many artists do to help settle themselves down before a performance? 

“I take a big ol’ shot of tequila [laughs], and then the band and I all get together and we put our hands in and someone will usually say some kind of quick, funny words, maybe, and then we always do a ‘Hell Right!’ Then we walk out on-stage. That’s kind of like become a thing, to where if we don’t do that, we know we’re gonna have a bad show. Because anytime we haven’t done it is usually when something goes wrong during the set. It’s like a little bit of a superstition for us.” 

Hailey has described herself as being both a “negligent optimist” and as being “born a little broken-hearted”, two descriptions which I find fascinating. I asked her to share a little bit more about what she meant in each of those cases…

“Well, I think being a negligent optimist is just me being foolishly positive! [Laughs]. I really am a glass half-full kinda person, and I just always have looked at things that way. Sometimes, Jake even will tell me, ‘You’re just not a realist’, but I’m always a little more head-in-the-clouds, ya know, [believing] things are gonna work out! And it’s gonna be great, there’s no need to stress or worry about it, that kind of thing. I just kind of act, I guess, with that mentality. Maybe I should be a realist, I don’t know! [Laughs]. Maybe I would be a little less broken-hearted when it doesn’t work out if I were that way [laughs]. And as far as being born just a little broken-hearted, I’m probably just naturally a little bit of an Eeyore sometimes. I love sad songs. Sad songs make me really happy sometimes. As far as my relationship with Nashville goes, it’s kind of been a little bit of a broken-hearted kind of thing. I have a love-hate relationship with this town in a lot of ways. But I’m a sucker for sad things, ya know, and I think sad things can sometimes bring us all together, and that is actually kinda quite beautiful.” 

Hailey has gone from having the dream of being a country music star – even buying herself a ticket to the Opry on her ten year anniversary in Nashville to try and reignite that dream – to now living that dream. And in doing so, she has become the inspiration for so many more people all across the world to keep fighting for and following their own dreams too. So, speaking to other dreamers out there, and speaking as Hailey the whole human being – songwriter, artist, girlfriend, friend, daughter, everything that she is – what’s her one piece of golden-nugget life advice? 

“I would say do what you love. Do what you love, with people you love. Life is so short, and it’s so easy to get distracted, and to sluggishly commit to things and to do things that we maybe don’t really want to do, but it’s for other people and not ourselves. So do what you love, what makes you happy, because I think the world needs a lot more happy people in it!” 

~ HAILEY WHITTERS plays C2C Dublin (Country-to-Country) at the 3Arena on Saturday, March 12th. Her debut album, THE DREAM, and deluxe edition LIVING THE DREAM, are both out now, available on all platforms. Hailey’s new album, RAISED, is out on March 18th. For more info, check out www.haileywhitters.com 


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s