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The Best Hailey Whitters Songs

April 24, 2023 8:30 pm GMT
Last Edited May 7, 2023 12:06 am GMT

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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 Album of the Year award last year for Raised 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 Hailey Whitters 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.

15
Big Loud | 2023

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.

14
Carnival Recording Company | 2015

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.

13

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.

12
Pegasus Records / Big Loud | 2020

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.

11
Pegasus Records / Big Loud | 2020

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.

10
Pigasus / Songs & Daughters / Big Loud | 2022

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.

9
Pegasus Records / Big Loud | 2020

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.

8
Pegasus Records / Big Loud | 2020

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.

7
Pigasus / Songs & Daughters / Big Loud | 2022

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.”

6
Pigasus / Songs & Daughters / Big Loud | 2022

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.

5

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.

4
Carnival Recording Company | 2015

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.

3
Pegasus Records / Big Loud | 2020

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."

2
Pigasus / Songs & Daughters / Big Loud | 2022

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.

1
Pegasus Records / Big Loud | 2020

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.

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Written by Jof Owen
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