Caylee Hammack Readies Next Era With Vulnerable New Single [Interview]
Capitol Records Nashville recording artist and ACM Award winner Caylee Hammack released her critically acclaimed debut album If It Wasn’t For You in 2o20. After years of touring, connecting with fans and being part of some incredible collaborations, she is ready to pull back the curtain on her new era of music, starting with the release of her new single “The Hill,” out today (June 14).
Hammack recently took some time to speak to MusicRow about her new music.
When she first moved to town in 2013, Hammack immediately got her boots on the ground and started playing in bars all up and down broadway. After two and half years of playing the bars and getting in as many writes as she could, she landed a publishing deal with UMPG Nashville.
Unfortunately, tragedy struck in Hammack’s life when she lost her home in electrical fire while at a writer’s retreat. Despite her hard times, the singer-songwriter found her support system here in town, and it showed her what she truly needed in her life.
While her personal life was down, she found that her professional life was going up through that support. At the time, Hammack was starting to hammer down on finding songs for her debut album. She enlisted friend and producer Mikey Reaves for song sampling, and a few of those demos are what you hear on the record today, such as “Family Tree.”
After signing her record deal in 2018, Hammack was off to the races on radio tours to begin introducing herself to industry gatekeepers. She released her debut album in August of 2020, and recalls how hard it was not being able to see fans reacting to songs out on the road, as being able to see music connect is vital to her.
“There’s just a tangible magic, connection and unity that I have with complete strangers [at shows]. That is one of the most beautiful things that music does. It’s a conduit for people and it connects us all,” she says.
“We have so many differing opinions, but for some reason, when that one song plays, people will drunkenly put their arms around each other’s shoulders and sing along together. For those three minutes, we agree on something and we’re happy together,” Hammack explains. “During that time, I realized in an ever deeper level what I already knew—that it is magic the way music is able to draw people in.”
Since live shows have come back, Hammack has been sharing her music with the world non-stop, opening up for Brothers Osborne, Brad Paisley, Darius Rucker and more. She also embarked on a co-headline tour in the UK with Tenille Arts, and has played CMA Fest, The Long Road Festival, Watershed Festival and more.
“I truly cried after the first gig back [from COVID]. There’s something about when you look out into a crowd. Someone once told me every single show that you play is most likely one person’s first-ever show and one person’s last-ever show, so you better play it that way. That’s how I’ve always viewed it.”
That’s why heading into this new album, Hammack is excited to take on a whole new approach by seeing real-time reactions.
“I feel like I’m getting to do [the album cycle for the first time] all over again. I’m working on these songs and am on the road at the same time,” she says. “We’re releasing stuff, getting to tour, getting to do the TV shows and everything versus just spending eight or nine hours a day on Zoom doing interviews, Instagram lives and DM-ing people and then laying in bed going, ‘I hope they like it.'”
Gearing up for the project, Hammack zeroed in on her sound and artistry.
“This next record is much more organically influenced and infused with more acoustic energy like the music I was raised on. On the first album, we did a lot of sampling and such because we were working with demo budgets. That album came out exactly how it should, but I remember listening back and it felt poppy for me. It doesn’t sound the way my heart sounds when I sing these new songs.”
Hammack enlisted trusted producers Dann Huff and John Osborne to co-produce her next album with. By letting her creativity flow with no limits and learning from Huff and Osborne, she’s confident that it will truly show who she is as an artist.
“I was able to truly fall into the bells and whistles, the little pad parts, the ways of layering things and certain effects that I love dearly. I had so much more freedom. I got to step back and truly be the artist.”

Hammack is a co-writer on all but one of the album’s songs, but feels her first outside cut was truly made for her. Her friend and fellow songwriter Mia Mantia played her a track she was working on that was a spin off of “Mammas Don’t Let Your Babies Grow Up To Be Cowboys.” This version was from the woman’s point of view, saying, “don’t let your babies grow up to love cowboys.”
The song struck a chord with Hammack, as it reminded her of a family member Matthew Rue, who had just passed away from complications with MS. Rue was a huge musical influence for Hammack, as he was her only musical family member.
“I heard it and thought of Matthew and the old country music that he loved. I got these goosebumps all over my body,” Hammack recalls. “I just felt like God was telling me that I needed to cut the song. It just was so serendipitous the way it happened and the way my body reacted.”
Lyrically, Hammack is sharing some of her favorite stories from her catalog, some tracks even dating back to 2018. She wants to share the vulnerable part of herself, hoping to cultivate connection to the fans.
“What I’ve learned is the songs that are the most vulnerable—the ones about the grittiest and saddest parts of my life—have been the ones that most people have connected to,” she shares. “When I realized that they connected to the vulnerable parts of me that I tried to hide, it gave me this new revival of hope.”
To start off the new era, Hammack released her new single “The Hill” today (June 14). Written with Tenille Townes and Logan Wall, the single kicks off the album’s vulnerability.
“‘The Hill’ is a white flag being waved by a broken arm in the middle of a battle. There is no point in fighting. If you win this argument, you might just lose the other person, so winning this argument is not worth it at all if you lose them.”
More of Hammack’s new music is on the way.
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