Top 10 Hailey Whitters Songs

Whitters' cover of the Dolly Parton and Kenny Rogers classic with ERNEST and COUNTRYPOLITAIN functions as a useful mission statement for anyone still wondering about Whitters and where she falls in country music's legacy: She honors country music tradition while at the same time clearing new, forward-thinking ground. Whitters' "Island In The Stream" would be at home on a Lo-fi Indie playlist or Dolly Parton radio. Therein lies the magic.

On "Ten Year Town," Whitters sings, "I thought I'd be a big star now / I'm twelve years into a ten-year town." The ten-year town is, of course, Nashville. The song reflects on the bumpy road artists must travel in hopes of eventually reaching success. She penned it in collaboration with Brandy Clark, whose career took a similar journey.

Whitters sings from a place of tired hope. "Waitin' on that break to come / All it's ever done is break my heart / I didn't come this far / To only go this far." Ironically, once the song was released in 2019 (first on social media and then on her independent EP), Whitters began to get attention from fans -- including Maren Morris.

You likely first heard the track "Happy People" in 2017, recorded by Little Big Town. The song was penned by Whitters and frequent collaborator Lori McKenna. Both songwriters eventually recorded their own versions for their individual solo albums.

Whitters' version of the optimistic tune is reminiscent of early Kacey Musgraves, with its harmonica and Whitters' quick-witted delivery. She once said in a press release, “This song has always felt like a step-by-step guide to happiness."

"Everybody Oughta" is the only song on Raised that's not written or co-written by Whitters. She told Songwriting Magazine, "It’s one of those songs that, when I heard it, I thought, ‘Man, I wish I wrote that.’ That’s kind of my bar for deciding when to cut an outside song, is it something that I feel like I could have said or wished that I had said?"

"Everybody Oughta" certainly sounds like something Whitters could have said herself. The track celebrates small-town living, which fits nicely with the nostalgic themes of Raised. It was written by Matt Roy and Craig Wiseman, and like Whitters, they gracefully sidestep the overdone and the cliche when they travel down memory lane.

There's a vein of keep-your-chin-up optimism that runs through Whitters' music, even when she's singing heartbreak songs. If there were a pageant for the Queen of Silver Linings, Whitters could very well win. "Dream, Girl" embodies this ethos.

On the track, Whitters reassures "a wallflower wishin' on might-have-been" that "you're someone else's dream, girl." She sings like the trusty big sister who's been through it all herself. (Fitting, given that she's one of six children.) What makes the song especially loveable is that Whitters doesn't just tell the young girl she'll be another boy's dream. She also gives her directives of her own: "Don't ever lose sight of your dream, girl / Never settle for less than you need, girl."

From the moment Whitters teased "Boys Back Home," it became a fan favorite off her album, Raised. The tune is a gift for us country girls who have sung along to song after song about countless farmer's daughters, girls next door, and hometown country girls that captured the hearts and imaginations of the men on county radio, all the while wondering, "Where's the song for us?"

Whitters was working on it. She sings, "They drive me around on those Friday nights / And they taught me to kiss, and they taught me to cry / When I think about all of the men that I've known / There ain't none like the boys back home."

Yes, it's sentimental, but it also offers us a precious chance to connect with our former, haven't-left-our-hometowns-yet selves: "Well, I left that town, and we all grew up / But sometimes I still miss that girl that I was / When I was a shotgun seat in their trucks / Singin' along to the radio."

"The Neon" was one of two singles released ahead of Whitters' third album, Raised. Since then, it's become one of Whitters' most-streamed songs. Its all-too-relatable lyrics and infectious groove are likely to blame.

Whitters co-wrote the song with Lori McKenna and Rodney Clawson. Its lyrics capture the aftermath of heartbreak: "Here comes the neon / Here comes the sad part / Salt on my wounds / Some blue on my broken heart / The stars we strung our dreams on / We shot 'em all out one by one / I'm turnin' off this porch light / I always said I'd leave on." Rhythmically, the track has a forward-moving pulse. At the same time, a mournful violin holds steady, making for a put-on-repeat-worthy listen.

"How Far Can It Go?" is one of five bonus tracks released for the deluxe edition of The Dream. Each track is a collaboration, and while it's hard to pick favorites amongst a group of such notable guests, Whitters' musical alliance with Trisha Yearwood is downright irresistible. The fun that the two women had while trading verses about betting on young love is audible.

Lyrically, "How Far Can It Go" sounds like it could be part two to Yearwood's classic "She's In Love With The Boy." With lines like,  "How far can it go? How long will it last? / She's got her eyes on forever, he's got his foot on the gas / You can't stop two hearts from findin' out what they wanna know / Town is guessin' people bettin' daddy's sweatin' / Hey, how far can it go?", we very well could be talking about Katie and Tommy.

"Everything She Ain't" was the first single released for Raised, and is Whitters' most popular track to date. The tune is catchy, clever, and confident -- signature Whitters. She co-wrote the track with Ryan Tyndell and Bryan Simpson and brings her best delivery to each and every word.

"Everything She Ain't" is the "You Belong With Me's" older, more self-assured country cousin. Whitters isn't pleading with anyone to notice her. She's telling it like it is: "She sees diamonds but I'm seeing stars / You should leave her on an island, dance with me in this bar / 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."

"Heartland" was first released during the lead up to Whitters' 2020 album, The Dream, but the track could have also felt right at home on Raised. The song is one of those country tunes that has wings for dreaming and roots for remembering home. In the tradition of The Chicks' "Wide Open Spaces," "Heartland" is a song to be sung with the windows down when you're finally setting off on your own path and saying goodbye to expectations.

In a poignant chorus, Whitters sings, "'Take it down a fast lane / Right back to your last name / To remind you where you came from / You're still shinin' in the same sun / It don't matter how high / You've been floatin' in your blue sky / Nothin' gets you like goodbye can / When life is out of your hands / Yeah, you gotta let your heart land." Pretty good advice, if you ask us.