Issue 008: Caroline Woodfill Is Saying Exactly What She Thinks

Caroline Woodfill does not need much time to tell you who she is.

She is from Texas. She likes country music simple. She likes to say exactly what she is thinking. She loves Jesus. She loves a good outfit. And if you come to one of her shows, there is a very real possibility she will say more than she probably planned to.

That combination is not something Woodfill is trying to polish out of her music. It is becoming the identity she is building around it.

She describes her sound as “very hillbilly,” but that answer only tells part of the story. Woodfill can be funny and loud one minute, unexpectedly thoughtful the next, while keeping the music rooted in straightforward country storytelling.

“I like to say what I’m thinking,” she says.

For Woodfill, that may be the simplest explanation of everything that follows.

From Willis, Texas to Nashville

Woodfill grew up in Willis, Texas, and says Nashville ultimately called to her for two basic reasons: she loved strumming a guitar and she loved turning whatever was on her mind into a song.

The realization that music might be more than a hobby came early and in a characteristically Caroline Woodfill way.

Her dad bought her a pair of heels so she could join the worship team. She enjoyed singing, and faith remained important to her, but Woodfill quickly realized she felt most alive when she was writing the kinds of songs that allowed her to talk about real people, real situations and whatever she actually wanted to say.

“I love Jesus too,” she says. “But it really resonated with me when I could just say what I’m thinking and write about it too.”

That was when the direction became clearer.

Woodfill knew she wanted to write songs that sounded like her.

The person who most encouraged her to believe she could do that was her mother.

Before she passed away, Woodfill’s mom continually reinforced the idea that pursuing country music and holding onto her faith did not have to be opposing paths.

“She always told me, ‘Come on, you can do the whole country music thing and you can love Jesus at the same time,’” Woodfill remembers.

Her mother’s death also arrived at a point when Woodfill was deciding what direction her life should take. She had considered playing volleyball and going to college instead of moving to Nashville. Losing her mom made that decision feel different.

Woodfill decided music was not something she could walk away from.

“After my mom passed away, I realized this is really what I’m called to do in life,” she says. “I just can’t give up.”

Loretta, Dolly and Being Completely Herself

Woodfill’s musical influences make sense almost immediately once you hear her talk.

Loretta Lynn was foundational. “You Ain’t Woman Enough” was the first song she really learned on guitar, introducing her to a kind of country songwriting that could be direct, funny, tough and unapologetic all at once.

Then there is Dolly Parton, an influence who reaches beyond music.

Woodfill admires Dolly’s willingness to dress how she wants, say what she thinks and carry herself without allowing everybody else’s opinion to dictate the way she lives.

Her third major influence is much closer to home.

Her mom.

“She always got her point across,” Woodfill says. “And I loved doing that.”

All three influences connect back to the same idea: identity.

Woodfill does not remember a specific moment when she stopped trying to sound like other artists because, in her mind, she never had much of a choice.

“I don’t think I could sound like anybody else,” she says. “There’s nothing really anybody else really sounds like this.”

There is humor in the answer, but underneath it is something Woodfill takes seriously. She can admire other artists without becoming them.

“I know in my heart that I can just only be me, and that’s the best I can be.”

That individuality shows up in the music, but it also shows up visually. Before seriously pursuing music, Woodfill considered fashion. She still loves vintage clothing, secondhand shopping and finding ways to create pieces herself.

Instead of abandoning that interest, she has folded it into the artist she is building now.

Fashion is not separate from the music for Caroline Woodfill. It is another part of the same personality.

“Take It Like a Texan”

If someone wants a quick introduction to Caroline Woodfill, she tells them to start with “Take It Like a Texan.”

Her reasoning is simple.

“That’s just who I am,” she says. “I’m just a Texan.”

The song captures the grit, humor and attitude she wants people to associate with her music.

Its origin story fits the artist almost too perfectly.

Woodfill was at a bar in Tennessee when a man approached her with a pickup line that did not exactly impress her. Her immediate reaction was essentially that no self-respecting Texan would have tried something like that.

Then came the phrase.

You can’t take it like a Texan.

Woodfill brought the idea into a writing room with Bryce Cain, and the concept became the song that has helped define this season of her career.

“If you want to mess with me, you got to take it like a Texan,” she says.

Woodfill wrote the song with Cain, while Jimmy Ritchie produced the recording. When she first showed it to him, his response confirmed what she already knew: the song sounded unmistakably like Caroline Woodfill.

That is increasingly the goal of everything she writes.

There may be humor, there may be a little chaos, and sometimes there may be more happening lyrically than a listener catches the first time through. But Woodfill does not want the experience to feel overly serious.

She wants people to have fun.

“Really why I write music is to let people know it’s not that serious,” she says. “Just have a good time.”

Learning Nashville at 19

Woodfill moved to Nashville at 19, arriving without much understanding of the machinery behind the music business.

She did not even know what a writer’s room was.

That changed quickly.

Nashville taught her how much of a career is built through relationships, communication and learning how to support the people around you instead of entering every room focused entirely on yourself.

“I think doing this, you need to support before putting yourself first,” Woodfill says.

That lesson has become one of the more mature ideas underneath an otherwise deliberately playful personality.

Woodfill loves meeting people. She loves hearing their stories. She loves creating with them. And over the next year, one of her biggest goals is simply expanding that circle.

More songs, more clothes and more hair might make the list too, if you ask her.

But the relationships matter.

“Hearing their stories inspires me to do this even more,” she says.

She has found some of that community through Nashville writers rounds, particularly Rebel Rouser, which she describes as one of the spaces that feels most connected to her.

At the same time, Woodfill has learned that being an artist in Nashville means doing far more than writing songs and playing shows.

Social media matters.

A lot.

She admits the constant pressure to post can be difficult, but she also understands that modern artists have to keep showing up online if they want the music to reach people.

The trick is persevering without becoming afraid that everyone is getting tired of seeing you.

Woodfill, unsurprisingly, has a joke for that too.

“How could you get tired of this?”

A Show That Feels Like Caroline Woodfill

There is no complicated promise attached to a Caroline Woodfill show.

You are probably going to hear her talk.

You are probably going to hear her say something she did not plan.

And, if everything goes according to plan, you are going to leave feeling like the ticket was worth it.

“Just know you’ll have a good time,” she says. “I’m gonna be there right with you. And I’m gonna make sure you have a show that you paid for.”

That desire to make people happy appears repeatedly when Woodfill talks about what she actually wants from a career.

Success is not only streams, followers or recognition.

It is making someone’s day brighter.

It is making someone smile.

It is being somebody other people can look toward and feel a little better because they did.

“At the end of the day, that’s all that matters,” she says.

One fan interaction made that especially real.

Woodfill was performing at a small state fair when someone approached her afterward. She assumed they had simply been attending the fair and happened to catch her show.

Instead, they told her they had seen that she was performing and came specifically to watch her.

“You came for me?” she remembers asking.

The moment was small, but it mattered.

“That just showed me that I got to keep going,” Woodfill says. “I can’t give up.”

Keep Dreaming

Before music became the focus, volleyball taught Woodfill one of the lessons she still carries into her career: keep pushing.

Talent without persistence is not enough.

“You just got to dream and dream and got to keep going,” she says. “A wish ain’t going to get you nowhere. But a dream will.”

If she could speak to the younger Caroline who first decided to pursue music, she would tell her essentially the same thing.

Keep going.

Keep dreaming.

Never stop.

“Once you stop dreaming, you stop living,” Woodfill says.

The dream is getting bigger.

She talks about someday playing Billy Bob’s Texas, opening for artists like Cody Johnson, Jason Aldean or Lainey Wilson, and eventually stepping into the circle at the Grand Ole Opry.

But for all the big stages she imagines, Woodfill’s definition of who the music is for remains remarkably uncomplicated.

Everybody.

The guys who want to have a good time.

The girls who want to yell about their exes.

Anyone with a sense of humor.

Anyone willing to come along for whatever she decides to say next.

Because underneath the outfits, Texas attitude, one-liners and hillbilly country music is something Woodfill returns to again and again.

She wants people to feel seen.

She wants them to feel loved.

She wants them smiling when they leave.

“Right now, I want people to know that I love them,” Woodfill says. “And I will be there for them, even in my music.”

That may be the contradiction that makes Caroline Woodfill interesting.

She can be loud without being careless.

Funny without pretending nothing matters.

Deeply rooted in faith while refusing to sanitize the personality out of her songs.

Country enough to call herself hillbilly, but curious enough to keep changing the recipe.

Ask her what the next chapter looks like and she has an appropriately Caroline Woodfill answer:

A hoot and a holler.

And somehow, that feels about right.

MUSIC CITY MUSICIANS | ISSUE 008
Caroline Woodfill & The Double D’s

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