Hailey Whitters Honors Perseverance With Deluxe Album Living the Dream

Photo Credit: Harper Smith

When Hailey Whitters wrote “Ten Year Town,” she was starting to lose faith in her dreams of making it big in country music. She’d written songs for Alan Jackson, Martina McBride and Little Big Town, but was still waiting for her own star to rise. “I’m 12 years in to a 10 year town,” she confesses in the heart-opening track, which kicks off her self-funded 2020 album The Dream. She didn’t know it then, but the unflinchingly honest song – about surpassing the time limit to “make it” in the competitive Nashville music industry – is also the one that catapulted Whitters from waiting tables to establishing herself as an artist. “Ten Year Town” helped her achieve many of the goals that come along with country music stardom, from going on the road full time opening for the likes of Maren Morris and Little Big Town to making her Grand Ole Opry debut.

“I really felt like I was living the dream,” Whitters tells Audiofemme of the her “career changing record” and the success that followed. “I was getting to see all these bucket list moments happen and these dreams that prior to this record I had really questioned – ‘Am I going to get to do this?’ ‘Am I going to get to see some of these dreams come true?’ I feel like that record really changed that for me and made that possible.”

Watching the way in which her life was transformed as a result of The Dream, producer Jake Gear (then Whitters’ boyfriend and now her fiancé) suggested making a deluxe edition, appropriately titled Living the Dream, set for release on February 26. The project features five new songs in the form of collaborations with Trisha Yearwood, Little Big Town, Jordan Davis and singer-songwriters Lori McKenna, Hillary Lindsey and Brent Cobb, each of whom Whitters attributes to playing a distinct role in her career.

The new collection begins with “Fillin’ My Cup,” a jovial take on the highs and lows of life and the people who make it all worth it, elevated by Little Big Town’s spirited harmonies. The Grammy-winning group played a significant part in The Dream, as Whitters used the royalty checks she earned from the band’s 2017 single “Happy People,” which she co-wrote with McKenna, to fund the album. On “Fillin’ My Cup,” their voices support potent truisms, like “You can’t appreciate the sugar if you never had the salt.” “It’s one of those lines that reminds me that this is all part of it. Take the good, take the bad, keep going, it’s going to swing back your way,” Whitters says. “All those saltier moments are the ones that come out and make life sweet.”

The native Iowan also called upon one of her childhood idols, Trisha Yearwood, to duet with her on the witty “How Far Can It Go?” an observational look at young love that would fit seamlessly on any ’90s country playlist. “Trisha’s a hero,” Whitters professes, saying she grew up “studying her records.” “She really inspired me to want to do this in the first place, so to have her on it is a huge dream come true.”

Meanwhile, Cobb, who has also taken Whitters out on tour as a supporting act, appears on the bluegrass-influenced “Glad to Be Here,” which finds the two singers on the grateful side of life, while the songwriting dream team of McKenna and Lindsey lend their talents to “How to Break a Heart.” Davis brought Whitters along as an opening act on his Trouble Town Tour in early 2020; here, he helps bring Living The Dream to a free-spirited close through “The Ride,” a tribute to the “burned out believers” and dream chasers. “It’s about moments. It’s about having some of those goals and dreams and getting to see them and appreciate the ride that gets you there,” Whitters notes. 

The young visionary has been intentional about honoring the journey throughout her career – because it’s those honest glimpses into her resiliency that helped her finally reach her goals. “Ten Year Town” showcases her determination (“I didn’t come this far to only go this far”) as well as her hopes (“This next song could turn it all around”) via defining lyrics that can apply to anyone still waiting on their big break – and for Whitters, eventually proved to be prophetic. “That language is very candid. It feels like a page out of a diary,” Whitters says. “Those are lines of persevering and continuing to keep going.”

Perseverance is an integral element of Whitters’ journey and subsequent success. The bright-eyed singer has begun to realize how even the simplest of life’s moments are complexly connected. She’s got some permanent symbols on her skin to remind her of that – visible in the video for “Fillin’ My Cup,” as she sticks out a thumb to hitchhike in a pageant-esque wedding dress. She sticks her thumb in the air, revealing a small tattoo of the letter “D” (honoring her late brother Drake) on her wrist and a delicate prairie rose in the crook of her arm, both symbolizing the deep connection she has to her hometown roots. The prairie rose is Iowa’s state flower, Whitters explains; Gear and her creative director Harper Smith, who sketched the design as a logo for The Dream – are also from the Hawkeye State. “I jog back at my parents’ house on the highway and I see the prairie roses in the ditch, and it always makes me happy,” Whitters says. “It makes me think of Iowa and makes me think of heartland.”

She and Gear had decided to get matching prairie rose tattoos after the album that ultimately changed the trajectory of Whitters’ career was complete. “It makes me think of that record that Jake and I built from scratch. It’s become a very meaningful symbol to me,” Whitters reflects, identifying how her roots are connected to her creative ambitions. “The more I’m forced to create, the more I’m forced to think about some of that stuff. I feel like I’m unraveling these layers that are freaky almost, how much they are intertwined.” 

The newest tracks on Living the Dream are Whitters’ way of expressing gratitude for her time here on earth, the people who’ve shaped her experience, and the dreams she’s carried in her heart that continue to unfold before her — passing that feeling of hope onto each person she reaches through her music. “I think in the most simple sense, living the dream to me is realizing how lucky we are to be alive,” she says. “I was looking at the people in my life who have died and who’ve died young. It was a big lesson in perspective to be able to look at that and think ‘How lucky am I to get to be a human being in this world and live and hurt and cry and laugh and love?’ It’s about feeling vulnerable in all those areas and in all those things.”

“My hope is [that] it shows those dreamers: this is what can happen when you don’t give up and keep going, keep chasing the dream,” she adds. “I hope it’s a story of inspiration.” 

Follow Hailey Whitters on Instagram, Twitter and Facebook for ongoing updates. 

CMT Next Women of Country Proves There’s a Sisterhood in Nashville

Each year in Nashville, the women of country music gather to celebrate one another and provide an important platform for the new artists working to break ground in the genre through CMT Next Women of Country.

Founded by CMT Senior Vice President of Music Strategy & Talent Leslie Fram in 2013, CMT Next Women of Country shines a spotlight on nearly a dozen promising new female acts in Nashville, providing them with tools and resources to be successful in a male-dominated industry, with past inductees including Kacey Musgraves, Maren Morris and Kelsea Ballerini. During the 2019 CMT Next Women of Country event co-hosted by Fram and Martina McBride at the Country Music Hall of Fame in Nashville, the 2020 CMT Next Women of Country class was unveiled, comprised of Gabby Barrett, Caylee Hammack, Hailey Whitters, Madison Kozak, Walker County, Avenue Beat, Abbey Cone, Kylie Morgan, Sykamore, Tiera and Renee Blair.

A consistent theme carried throughout the annual event is empowerment, whether the artists are championing one another or singing introspective and thought-provoking songs they’ve penned. The 2019 event reflected the variety of the music these women are creating through an acoustic songwriters round that invites each of the new inductees to perform an original song. Caylee Hammack delivered a stirring performance of “Small Town Hypocrite,” a song inspired by the ex-boyfriend she gave up a scholarship for who ended up cheating on her, while Hailey Whitters also proved to be a compelling songwriter with her depiction of a fictional character named Janice, an 80-year-old woman who offers sage life advice like “stay off the pills, but get on the pill if you ain’t ready to start a family,” the line calling to mind Loretta Lynn’s 1975 feminist anthem, “The Pill.” Madison Kozak, the first artist signed to Nashville’s new all-female label Songs & Daughters led by groundbreaking songwriter Nicolle Galyon (Camilla Cabello’s “Consquences,” Dan + Shay’s “Tequila”), held every heart in the room like it was made of glass with “Household,” touching on the universal feeling of wanting to leave home, but longing for that very place when you’re finally gone.

Photo by Rick Diamond/Getty Images for CMT)

The talent displayed in the room reflected country radio’s glaring lack of inclusion for such artists. In December of 2018, it was reported that for the first time in the 28 years since the Billboard Country Airplay chart launched, there were no women in the Top 20. However, up-and-coming artists are slowly fighting their way out of these alarming statistics, as Hammack’s debut single “Family Tree” has cracked the Top 40 on the country charts, Ingrid Andress is in the Top 20 with “More Hearts Than Mine” and Runaway June became the first all-female trio since the Dixie Chicks to have a Top 5 hit with “Buy My Own Drinks.”

But the conversation surrounding the lack of women on country radio still lingers, with Mickey Guyton remarking on “the elephant in the room” the moment she took the stage to open the show. “There is without question an injustice happening to women in country music. There are a lot of great songs that are not getting a shot,” Guyton professed before performing her new song “Sister” with her country music “sisters” Tenille Townes, Clare Dunn, Rachel Wammack and Leah Turner. “But one thing is for certain: it is going to take us women to lift each other up out of these trenches.”

A burgeoning superstar who has gone above and beyond to support her female contemporaries is Brandi Carlile, who was honored with the Next Women of Country Impact Award. Carlile, who scooped up three Grammy Awards in 2019 for her acclaimed album By the Way, I Forgive You, has made it an integral part of her mission to elevate the women around her, curating the all-female stage at the 2019 Newport Folk Festival that featured her supergroup The Highwomen and a surprise performance by Dolly Parton, in addition to creating the women-centric festival Girls Just Wanna Weekend. She’s also pivoting her support for women into a behind-the-scenes role, serving as co-producer of Tanya Tucker’s new album While I’m Livin’ with Shooter Jennings.

Photo by Rick Diamond/Getty Images for CMT)

Rather than point a finger at country radio, Carlile encouraged radio employees in attendance to be intentional about the songs they’re sharing through the format while expressing the reverence she has for the genre that raised her. “If country music is the story of rural America, then what is the story that we’re telling to our young girls?” she questioned. “What we’re hoping, and what we’re inviting country radio to do is to catch up with the way that we all understand. I would urge anybody that’s involved in country radio…ask yourself the question every morning before you go to work ‘what do I want my job to say to my daughter today?’ Because she’s an American girl, she’s in love with a boy, she needs wide open spaces, she’s a wild one,” she continued, referencing iconic songs by Trisha Yearwood, the Dixie Chicks and Faith Hill. “She’s more than a pair of blue jeans in a cab of a truck.”

Additionally, a handful of behind-the-scenes movers and shakers were present at the ceremony, including Cindy Mabe, president of Universal Music Group Nashville, who made it a point to continue to call for change in the industry regarding support for women. “We can all keep moving through and thinking that things have changed at the rate that they need to change, and they haven’t,” she stated. “This is about how we give a voice and a perspective to half the world.”

She encouraged emerging artists to explore other methods of promoting their music outside of radio, pointing to artists like Musgraves, who received little attention from radio for her Grammy winning Album of the Year Golden Hour, instead reaching listeners through other formats like social media. “Women are bringing more adventurous, interesting, state of the art, cutting edge music and it doesn’t go and fit in a box. We will spend the next years figuring out how we get it exposed, one foot in front of the other,  because great music should always rise and it’s not about fitting into a box,” she said, actively taking Carlile’s words to heart. “I have to get out of bed every day and make a movement towards making women’s voices matter again.”

The program continues with the CMT Next Women of Country Tour, headlined by Tanya Tucker, in early 2020, with supporting acts and dates to be announced in the coming weeks.