“Watch Me”
Country music singer Sicily Rose charts a path from Montana to Nashville
On a small tract of land on the outskirts of Billings, the sun is setting, casting a golden glow on the rolling hills of wild land. Goats roam nearby and a small barn is home base to two striking Appaloosa horses. It’s here that 20-year-old country music singer/songwriter Sicily Rose is taking a break from the electricity of Nashville to do exactly what she loves most, hanging out with her horse, Cowboy, and leaning on the woman she credits with making her who she is today. That woman is her mother, Jamie Jones.
“A lot of who I am came from my mom — how strong and independent she is, showing me that you can do it on your own. You can figure out how to be an independent person,” Sicily says. “I witnessed that my whole childhood.”
Leaning up against a rugged fencepost, Sicily’s turquoise-adorned fingers strum on the strings of an acoustic guitar. Her lyrics paint pictures. Cue up her song, “Watch Me,” and you’ll get images of her childhood, long before she landed in the epicenter of the country music industry.
“She didn’t plan to be a single mama, pretty soon, that’s what she was. So, she took three jobs, spent all her time off taking care of all of us. When I was old enough to know, I asked her, ‘Are we gonna be alright?’ She got that fire in her eyes, said ‘baby girl, damn right.’”
“There have been tough times, but we always got out of the hole. I’ll just put it at that,” Sicily says.
Born in Elko, Nevada, Sicily’s father worked as a gold miner. Her mother, whom she calls a “gypsy,” was originally from Las Vegas. After Sicily’s parents divorced, when she was just a toddler, she, her mom and her two siblings, Zander, now 22, and Serin, now 18, “traveled and moved a lot,” spending time in different spots before finally settling in Montana when she was 10. “We fell in love with it,” Sicily says about Big Sky Country. She remembers walking to Beartooth Elementary, and hers was one of the first classes to attend Medicine Crow Middle School. Through it all, Sicily says her mom was a hair stylist and bartender, a woman who would help friends here and there, just to make money to support her family.
“She would work very long days and very long nights, and I watched her make sure that all of us kids were always taken care of, no matter what the situation was,” Sicily says. “We are a very tight-knit family. It’s always been us four.”
But even through the rough spots, Sicily says, “My mom always showed us, there’s a light at the end of the tunnel. There’s always a rainbow after the rain.”
When Jamie thinks of Sicily’s youth, she remembers a spunky girl with a spark of creativity. Sicily wasn’t afraid to tell her mom that one day she’d be a star.
“She told me she was going to be famous from the time she was 2. I didn’t really have a choice,” Jamie says with a chuckle. “It wouldn’t have been what I chose for her, but I saw her determination and how hard she was trying. This is what makes her happy.”
As Sicily grew, so did that spark. “She's very talented, and I saw that,” Jamie says. “Every time she's ever walked into a room, she's made sure that everybody knows her name before she walks out of it.”
Sicily laughs as she recalls one of her first brushes with local fame. She was 11 years old, walking down a makeshift runway in Rimrock Mall’s center court. David’s Bridal was putting on a fashion show and Sicily was chosen as one of the models. It wasn’t long after that she signed with the Montana-based Rocky Mountain Agency. “That just kind of started it all,” she says.
What followed was a successful modeling career. Sicily was eventually represented by Wilhelmina Models, one of the world's leading modeling agencies. It was a fast-paced life for a girl who was still a teenager.
“I would say that I’m an old soul,” she says. “I feel like I grew up very fast in my own head. I wanted to be as much of a help to my family as I could.”
Her work took her to Los Angeles and into national campaigns before she ultimately realized, at the age of 16, it was singing and songwriting that set her soul on fire.
“I’ve always loved music,” she says. “When I got into songwriting, it was the best way I could express myself and find out who I truly was through the songs. Music has just always been there.”
It’s why this young woman, wise behind her years, packed up her things two years ago to move to Nashville to pursue country music full time. She spent long days building up a social media following, knowing that younger country music fans often discover artists through TikTok, Instagram Reels and streaming playlists rather than traditional radio. The hard work paid off. Today, her content across social platforms has generated more than 300 million views, making her one of the more established media creators among promising country music artists.
“The goal was always music, but to get my foot in the door, I started with influencing and building up a brand,” Sicily says. “It makes it easier when you have a base following. It’s gotten to the point where I feel I can have the music career that I want and the one I have always dreamed of.”
Her social media presence is how she turned the head of one of Nashville’s biggest names. Earlier this year, Sicily signed with Off Road Records, an independent country label launched in 2025 and led by producer and label executive David Fanning. He’s a man known for his eye for emerging talent. On Off Road Record’s website, Sicily is featured as one of the label’s flagship artists.
To give some perspective, just four years ago, Fanning co-wrote the song, “Tennessee Orange,” which helped launch country music singer Megan Moroney’s career. In 2024, she landed the title of New Artist of the Year at the CMA awards. Fanning is known for being interested in artists with a genuine story to tell.
When Off Road announced Sicily’s signing, Fanning said, “Sicily understands the power of honesty in a song. (Her song) ‘Annabella Mae’ is a strong introduction to who she is as an artist and reflects the kind of songwriter and storyteller we want to build with at Off Road Records.”
“David Fanning is the best thing that could have happened to me in this moment of my life,” Sicily says. “He is an amazing manager.”
Since Off Road Records started managing Sicily and Reservoir Media began producing her music, she’s been working hard to build her catalog of songs with the label. Her first, “Annabella Mae,” is a brooding song that weaves a story of a wild spirited woman who gets caught up with the wrong man, and he ends up taking her life.
Next came “Vivian,” which Sicily wrote for her best friend. “She’s been through a lot and I wanted her to know that I am not going anywhere no matter what the hardship is. It’s one of my favorite songs I’ve written,” she says.
Her latest, “Forget Me Not,” is already on the rise with fans. “It’s one of my most streamed songs,” she says. At last check, the song had just shy of 350,000 streams on Spotify, which Sicily called amazing. “It’s a song about the fact that you don’t need a man to do things in life.”
When we met up with Sicily, she described herself as songwriter who has the notes app on her phone constantly open, helping her to churn out new lyrics whenever inspiration strikes.
“I wake up in the morning and say, what can I bring to the write today that will be something that no one has heard? What is a story so interesting that it makes a person sit back and think about it?” Sicily says. “There’s a song in everything. There is music everywhere. No matter the situation, there’s a song in it.”
As Sicily talks about her career, she longs for the day she’ll be able to take her show on the road.
“I am hoping in five years that I’m on the road touring,” she says. “I have a lot of music out and have built an amazing fanbase, but I'm also hoping I'm on the road touring and playing shows. That’s all I can really hope for.”
That brings us back to the song “Watch Me.” Sicily might have penned that song years ago, but the words are an anthem to this up-and-coming country musician.
“I set my sights on mountain tops and nothing less. Don't listen to the haters and the play-
It-safers out there tryna stop me. Just watch me. Hey world, watch me. Mama, just watch me.”
Her “mama” is indeed watching.
“I’m so proud of her. We are all so very proud of her,” Jamie says. “It’s fun to watch someone chase their dreams, watching how far she’s come.”
As Sicily walks across the land that surrounds her mom’s house, she might live in Nashville but this place on the outskirts of Billings will always be home.
“I truly love this place more than anything,” she says. “I never want to lose my roots. It’s where I grew up and watched life happen. I never want to lose that because I think it made me into the person that I am today.” She pauses before adding, “It made me a better person.”
Editor’s Note: Special thanks to Stone Feather Road for providing Sicily’s wardrobe.
