The Best Hailey Whitters Songs

Roulette on the Heart (with Conner Smith)

Connor Smith enlisted the reigning ACM Awards New Female Artist of the Year for this single, taken from his Smoky Mountains album.

Co-written by Smith with Jessi Alexander, Chase McGill and Mark Trussell, 'Roulette on the Heart' found the the pair gambling on a relationship they know could end in devastation but feel is still worth the risk.

“From the moment I wrote ‘Roulette On The Heart,’ it felt like finding a new level as a songwriter and having Hailey Whitters believe in this song alongside me only took it to another level,” Conner Smith says. “This song feels like it could live for a long time.”

Whitters added, “I first heard ‘Roulette On The Heart’ while playing radio shows with Conner Smith, and was so honored when he asked me to sing on the song. I love how realistically the song captures the intoxicating and sometimes toxic feelings of being in a complicated relationship.”

Glad To Be Here (feat. Brent Cobb)

Taken from the deluxe version of The Dream: Living The Dream, this collaboration between Hailey and Brent Cobb is a paean to taking life as it comes and being grateful for the good days when you get 'em.

"Some folks they focus on the broke spoke / Not me, I'm so over things I don't and coulda had," the pair sing. "Bring on the good, bring on the bad / 'cause even if the end is near, I'm just glad to be here."

It's always the first song on any chill country playlist we make and it's best served with a pitcher of margarita on a sunny afternoon.

Everybody Oughta

This wholesome ode to the simple things in life from Raised takes pays tribute to the things we all go through growing up; from learning to ride a bike to kissing in the rain. It might be messy sometimes but that's what makes us who we are. You'll get no judgement from Hailey, even if you don't want to do it all.

"I ain't sayin' that everybody's gotta," she sings before delivering one of her trademark vowel twisting rhymes. "But man, everybody oughta."

Tie'r Down

"If you don't love me at my worst," Marilyn Monroe once quipped. "Then you don't deserve me at my best."

Taken from Hailey's 2023 EP I'm In Love, 'Tie'r Down' is a reminder for everyone to find someone who loves them unconditionally.

“It's no secret I grew up a kid on '90s country radio, and so when I went in one day to write with Rodney Clawson and Chris LaCorte, I was reminiscing about Trisha Yearwood's song 'XXX's & OOO's' and I was thinking a lot about the way that song made me feel," Hailey explained about the song. "Strong and like I could do anything I set my mind to despite whatever barriers anyone or anything might put in my way. I wanted to write a song that made young girls growing up in today's world feel that same feeling.”

“This song is written in the third person, but there's a lot of me influencing the character in this song. There's dirt under my nails most of the time, and I'm much more ponytail in a ball cap than designer clothes. One of my favorite lines is, 'She's got a baby doll face but she's steel toe strong' because it says I may look delicate but don't underestimate my strength. That line always gives me guts whenever I need to go out there and show the world what I'm made of.”

American Gothic with Stephen Wilson Jr.

Written by Hailey Whitters with fellow cornfield kid Stephen Wilson Jr., there’s more than enough of Hailey’s inimitable charms lighting up this song to make it a must-add for any list of her best songs.

Inspired by her favourite Grant Wood painting, they sing this grungey paean to middle America from the tops of their little town lungs.

Black Sheep

“Go on and tell that Little Bo Peep, don't come lookin' for this black sheep,” Hailey sings in this anti-fairytale about not fitting in and being just fine about it, taken from her first album. Her sound might have been a little less refined than it was by the time The Dream came out five years later, but the song is an absolute belter.

The Ride (feat. Jordan Davis)

With a lyric that’s like a cross between a road song and a self-help book, Hailey and Jordan Davis put a reassuring arm around our shoulders to let all those “dead-end boys”, “break-down girls” and “burn-out believers” know that everything’s going to be alright in the end, even if it might not feel like it right now. After all, “It's the road that makes the ride.”

Put that on some driftwood and hang it in your bathroom.

Heartland

This halfway stop from The Dream has some of Hailey’s most vivid and vulnerable lyrics hidden away in it. “I should have an alibi on where time goes when it flies,” she sings as she winds the window down and takes a road trip back to the past to find out what she missed out on while she’s been following her dreams.

Loose Strings

Hailey’s picking over the mess of a relationship that’s run its course as she cleans out her car the morning after an argument and find hey lover’s jacket curled up in a ball on the backseat.

All she remembers is him throwing her car keys out because she was in no fit state to drive, and how she “staggered home alone” thinking about how strange it is the way they keep trying to stay together when the connections holding them are so fragile.

The way she sings "strings" like "strengs" and refers to the police as the "po-po" are reason enough to include this song.

Beer Tastes Better

Hailey Whitters followed up The Dream with a collection of songs that paid tribute to all the tiny towns across America like the ones she’d grown up in.

In some ways the follow-up was almost a prequel of sorts, as Raised found her going back to the girl she was before Nashville, to the people and places that inspired and encouraged her to move nine hours away and pursue country music.

Written over Zoom with Lori McKenna, it perfectly captures that bittersweet taste of having a beer wherever you came from with all the old friends you left behind.

Happy People

Another Lori McKenna co-write, ‘Happy People’ had been cut by Little Big Town and McKenna herself before Hailey got her shot at it and turned it into a harmonica heavy country funk classic with. It’s one of those songs that’s so simple you can’t believe it hadn’t been written before.

The Days

Turning to another of the Love Junkies, Hailey teamed up with Hillary Lindsey and Ben West for this song from The Dream, as they reflected on growing up and how fast time flies, resolving to just go with it and make every single day count instead of worrying about it.

In A Field Somewhere

Anyone who grew up in the countryside knows that you do most of your growing up in the great outdoors, more often than not in a field somewhere. Hailey looked back on all the lessons she learned in those Iowa corn fields to close Raised.

“Whenever I go home, I take a beer to the field out behind my parents’ house,” she explains, “sit in a lawn chair and soak it up. It’s kind of a holy place to me.”

I'm In Love

Where The Dream focused on Whitters' experience in Nashville and Raised looked back on her life in the heartland, the I'm In Love EP found her tapping into her '90s country influences while exploring relationships, heartbreak and finding love.

“I knew the minute I heard this song I had to record it," Hailey said about the title track, written by Nicolle Galyon, Lee Miller and Cameron Bedell. "I didn't write it, but I wish I had. I love - pun intended - the quirky language and spirit. Every time I sing it I'm smiling like a big ol sap because it just makes me so happy and puts me in a good mood.”

Middle of America (feat. American Aquarium)

Written with Bobby Pinson over Zoom, it’s probably the closest Hailey’s ever got to cutting a protest song.

BJ Barham’s impassioned vocal transforms the song into a rousing heartland rock anthem about a “bunch of patchwork dreamers” and “better believers” drinking vodka-spiked lemonade under the bleachers, before it turns its indignation on a government that threatens farming communities by building over the land they rely on.

How Far Can It Go (feat. Trisha Yearwood)

An addition to the deluxe version of her sophomore album, Living The Dream, this sounded influenced by Trisha Yearwood’s own country girl-next-door sound and could almost have been a rewrite of ‘She’s in Love with the Boy’, as a young couple fall in love and their parents wonder if it will all work out.

It was fitting that Hailey chose to get Trisha in on it too, and even if they didn’t get to record it together, they still managed to make an iconic video together to go with it once it came out.

One More Hell

This heartbreaking autobiographical song off Hailey’s debut album was written after her brother passed away in a car accident and the raw tenderness in her voice makes it one of her most powerful moments.

If you're choking up when she sings lines like “Mama’s not right, Daddy’s still mad / He wants to kick God’s ass ‘cause he says that it ain’t right he took you so fast”, then the home video that accompanies it will finish you off.

Janice at the Hotel Bar

Written with Lori McKenna, this song was inspired by a real life encounter that a friend of Hailey’s had with an 80-something-year-old woman named Janice in a hotel bar who dished up a lifetime’s worth of advice when she sat down beside her.

With a knack like Dolly Parton’s for picking out a simple line and instilling it with a deep, touching universal truth, it contains one of Hailey’s trademark pearls of wisdom: "Go on and make a good living, but don't forget to make a good life."

Everything She Ain't

Written with Ryan Tyndell and Bryan Simpson, this song is Hailey Whitters at her girl-next-door catchiest best as she reels off all the ways that she’s everything her romantic competition is as well as being everything she isn’t too. I know who our money's on.

Ten Year Town

Nashville is known as a 10-year-town because that's about how long it takes to make it there, and Hailey Whitters had been there 12 years when she wrote the song that ended up breaking her as a solo artist.

Although Hailey had had success as a songwriter for other artists, she felt like the clock was ticking on her own career and missed her family back home in Iowa. So she poured it all into every single second of this beautifully poignant song.

Thankfully she didn't have to wait another year. Written with Brandy Clark, ‘Ten Year Town’ went on to be the song that broke Hailey Whitters when it was included on The Days EP in September 2019 and then as the first track on her album The Dream in February 2020.