Annie Bosko Reflects On Her Roots and Rising Career With Debut Album, ‘California Cowgirl’

Bosko recorded songs written by Lainey Wilson and Garth Brooks.

By

Madeleine O’Connell

| Posted on

October 22, 2025

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11:09 am

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Annie Bosko; Photo by The RIker Brothers

Annie Bosko is proudly embracing every part of who she is in her debut album, California Cowgirl. In honor of the project, out now via QHMG/Stone Country Records), we caught up with the rising singer/songwriter to learn why this collection marks a defining moment for her and how she’s proudly blended her California upbringing with her country roots.

Across the album, produced by Trent Willmon and David “Messy” Mescon, fans hear a few epic collaborations with Dwight Yoakam and Darius Rucker, plus songs written by Lainey Wilson and Garth Brooks. Bosko also leans into her love of western sounds, fiddle and steel guitar, and taps into the kind of storytelling that has shaped her love for music by serving as a co-writer on over half the tracks.

Annie Bosko; Photo by The RIker Brothers
Annie Bosko; Photo by The RIker Brothers

She also discusses how writing empowering anthems like “Country Girls! (Who Runs the World),” and reconnecting with the raw honesty that first drew her to country music has all helped shape California Cowgirl.

Keep reading to learn more about the stories behind her debut album, the lessons she’s learned about authenticity, and how she’s preparing for the opportunity to join Dolly Parton for Dolly: Live in Las Vegas at Caesars Palace in 2026.

What does the album title mean to you, and how does it reflect your personal story in the title track?

The album title is very autobiographical; it’s who I am at my core. There were a number of years, when I first moved to Nashville, when I almost hid that I was from California because people perceive me as not being country. The older I’ve gotten, the more I’ve really embraced who I am. I’m proud of who I am. I’m proud of my roots and where I come from. I am the daughter of a third-generation farmer in California, and I was raised on traditional country music with a traditional upbringing. We said grace every night before dinner, and my mom cooked dinner every night. She was a stay-at-home mom, which I still consider to be the hardest job in the world. I think there’s a lot of stereotypes that come with being from California, and I’m really not any of those things. That’s what the title track is about, is that you might look at me and make assumptions because I’m wearing heels or something, but really I’m pretty down home.

How did your upbringing in California influence the rest of the themes and sound of the album?

My upbringing in California had a large influence. Thematically, “Rolling Stone” is about not really feeling like you fit in. I grew up in a place where a lot of people settle down very young – and don’t get me wrong, I definitely want that someday – but I just didn’t choose that path. I chose an unconventional path by pursuing music.

“Maliblue” is about a girl who goes to Malibu to try to get over her heartache, but no matter where you are – even in paradise – you can still be miserable. Sonically, it has a more traditional western country sound; it’s not what you’d expect from the title. I’ve always been so passionate about western music – and by that, I mean anything Texas-West – so fiddle, lap steel guitar, baritone guitar, those elements that come from country western swing.

I think Merle Haggard put it best: western music was born out of the honky tonk, while Nashville music was born out of the church (the Ryman and the Opry both stemmed from that). I love Buck Owens, Merle Haggard, Dwight Yoakam – all that western sound. I love anything that sounds like a Clint Eastwood soundtrack, and I tried to carry that thread throughout the album and keep it authentically country.

Annie Bosko; California Cowgirl
Annie Bosko; California Cowgirl

There are some awesome collaborations on this project. Were there any moments in the studio that stood out as especially memorable or surprising while working with these other artists?

Working with Dwight Yoakam was a bucket list moment for me. I consider him to be not only one of the greatest artists of all time, but an icon, and to be an icon, you have to leave a unique fingerprint on music history, and that’s exactly what Dwight has done. He has made music that’s both commercial and timeless, yet he has never broken or lost his artistic integrity. Everything he does feels intentional and true to who he is, so getting to collaborate with him was one of the greatest honors of my career. Working with Darius was so impressive on “Old Friends.” He is such a pro and is laser-focused when he goes in to record, which I really appreciate. I think Joe has one of the greatest voices in country music history. It’s so unique, so when you hear it, you just know it’s Joe Nichols.  

Along with the featured artists, names like Lainey Wilson and Garth Brooks appear in the credits. How did these particular songs land in your hands?

I believe in choosing great songs no matter where they come from. Kris Kristofferson would record Willie Nelson’s songs and vice versa, and it’s like, “Why not?” If there’s a great Lainey Wilson song out there that she didn’t record, why not give it a home? I don’t feel as though I need to write everything I record, and Garth Brooks is probably the greatest role model when it comes to that. He didn’t write “The Dance” or “Friends in Low Places,” and you could say that Garth Brooks would not be Garth Brooks without those songs. He also wrote undeniably huge hits like “Much Too Old” or Two of a Kind (Workin’ on a Full House)” so he wrote great songs, but he still found great songs, and I believe in doing that.

What do you hope listeners take away from hearing these songs top to bottom?

I hope that listeners listen to this front and back and it surprises them to discover new elements, angles, sides of who I am. I also hope it speaks to them and helps them with whatever they’re currently navigating in their life, because that’s the gift of what music did for me, particularly as a kid. It still does now, but when I think back to when music really hit the hardest, it was when I was growing up. It helped me get through the day.

Annie Bosko; Photo by The RIker Brothers
Annie Bosko; Photo by The RIker Brothers

Tell us about track No. 8, why you decided to add an intro before “Cowboy Up.”

It goes back to my love of old westerns, like something out of a Clint Eastwood or Tarantino movie. That intro has a fun, spaghetti-western-style lick that feels unique and sets the scene. You’re kind of wondering, what’s happening?, and then bam, the song kicks in.

“Country Girls! (Who Runs The World)” is such a fun anthem. Why was it important to make a song like this “for the girls!”

It was important to make a fun song like “Country Girls! (Who Runs The World)” because I wanted to pay homage to the songs that made me want to pursue this in the first place. All my favorite artists had deep, moving beautiful songs that would rattle my soul, but they also had fun, anthemic songs – I always think of Shania when it comes to balancing those – and it was like they were saying, “Don’t forget to have fun,” and that feels like a big part of my personality. I feel like there’s so many anthems from a guy’s point of view, singing about a woman and what makes her special, so I wanted to fill the void and have an anthem about a badass woman from the viewpoint of a woman.

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How do you plan to bring the album’s energy and storytelling into your live performances? And which songs from the album are you most excited to perform on tour?

I plan to bring the album’s energy and storytelling to life by showcasing all the different sides of who I am as an artist and as a human being. My goal for every show is to tap into the full range of human emotion. I want the audience to feel like they had a lot of fun, but also maybe they shed a tear. So many of us suppress those feelings day-to-day, and that’s what’s so powerful about live music — it lets you access those emotions you’ve been carrying around or hiding. That’s the magic I hope to create every night.

“Watch Me” is my opener and probably one of my favorite songs to perform live. It’s a total hype song, and I love the message of, “You don’t think I can do something? Well, watch me do it.” And sometimes that can be your own negative voice that you overcome, or the Devil or the industry. People will always tell you why you can’t do something long before you’ll ever hear why you can. But every impossible thing stays that way until somebody finally does it – and eventually, someone always does.

Talk about your goal to get back to real honesty on this record. Why was that an intention for you with these songs?

My goal in getting back to real honesty was about returning to the core of who I am, that little girl who first fell in love with country music. I wanted to reconnect with what made me love it in the first place: the fiddle, steel guitar, storytelling and the messages that spoke straight to my heart. Getting back to that pure, honest place was really important to me on this record.

You were asked to join Dolly Parton for her upcoming Las Vegas shows. Even though they have since been delayed, what does that opportunity mean to you?

It’s going to be such an incredible honor. I consider it one of the greatest opportunities of my career. She’s not only one of the most iconic artists of all time, but also one of the greatest human beings and businesswomen the world will ever know. I can’t think of a better role model for women, both in music and in life. It’s really a little “God Wink” moment for me (not to quote my own song). But as a female artist navigating this industry, the opportunity came at a time when I really needed it the most and feels like a sign that I’m on the right path and to keep going.

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Madeleine O’Connell graduated from North Central College with a bachelors degree in Journalism and Broadcast Communications before deciding to pursue her studies further at DePaul University. There, she earned her masters degree in Digital Communication & Media Arts. O’Connell served as a freelance writer for over two years while also interning with the Academy of Country Music, SiriusXM and Circle Media and assisting with Amazon Music’s Country Heat Weekly podcast. In addition to Country Now, she has been published in American Songwriter, Music Mayhem, and Holler.Country. Madeleine O’Connell is a member of the Country Music Association and the Academy of Country Music.