How did "Hole In The Bottle" land on Kelsea?
I thought I was done writing for Kelsea, and I was down in Florida with some of my favorite songwriters. We went to dinner to celebrate being done with the album, had a good amount of wine, came back, and almost jokingly wrote "Hole In The Bottle." It was just this fun, collaborative jam session. We were totally free to be silly. The next morning, we all listened to the demo, and it was a mess [laughs], but it was something that I definitely didn't have on the album. I was like, "This would be a really fun live song." It [made] the album at the very last minute. It ended up being the perfect song to put out in this climate. My favorite thing about music is it can be escapism if you need it to be. And this song is two minutes and 30-something seconds of escapism.
You've said that "Hole In The Bottle" is your first "drinking song," and it also taps more into the traditional country sound than your other work. What made you take those directions?
I try to hold myself to a lot of grace, and I really take being a role model very seriously. So I don't really get to tap into the normal me a lot, and this captures how I am in my living room with my friends. It's honestly still a blend [of genres], and I love it. It kind of taps into that traditional, almost "chicken pickin’" country, but it also has trap beats in it. From the beginning of my career, I've always loved rooting it in country, but having other influences, whether it be pop or trap music or R&B or whatever. The blend is always something I'm looking for.
Do you feel like the country music world has become more welcoming of that kind of genre-blending?
It goes in waves, just like every trend in music. But I definitely feel like over the last five years, the massive crossover hits that have happened are bringing a new audience into country. There will always be purists that only want to hear certain kinds of country music, and I respect that, but I also think that country music's always been evolving, and a lot of the — especially — women that I grew up listening to, that are now pillars in the industry, were people that were pioneering the sound. That's something that I intend to keep trying to do.
You reimagined every song on Kelsea for Ballerini. How did you approach this one?
To be honest with you, it was the hardest one out of all 13 songs to reimagine, because it's so specific. We decided to make it sound like you were walking into a bar off Broadway [in Nashville] and there's a jam band that plays together every Friday — they have for 30 years, their best friends are seasoned musicians, who have played on hit records, but they just jam on Fridays — and it's their interpretation of the song. That's kind of how I wanted it to sound. So it's a little more musical, a little more messy. It sounds like the dive bar version.
What did you learn from the process of making Ballerini?
I learned that a song should be strong enough to stand in different ways. Even though we made Kelsea to be the best thing I knew at the time, the songs were strong enough to undo and redo. It shows that I should always focus on the lyric and what the song stands for and then build around that. In general, this year has taught me to stop putting so much weight in a plan, because sometimes, the pivot is where the good stuff happens. I'm such a planner that I get really caught up in that. It taught me to stay lighter on my feet and be able to pivot when I need to.
So...we have to talk about Shania.
Oh, we have to.
How did she end up on the "Hole In The Bottle" remix?
I've known Shania for a few years now, which sounds silly even saying. At the beginning of the pandemic, she reached out about doing something together. We spent a couple of months going back and forth on song ideas, but it wasn't until I watched the “Hole In The Bottle” music video back that I was like, "Wait a second. I idolize this woman. She's one of the main reasons I am a female in country music. And I tip my hat to her in this music video." She has this wonderful, witty sense of humor, and this banter that she's known for in her music, that this song lends itself to.
So I literally just asked her. I sent her the link to the video, and I was like, “I kind of play off of your leopard print and your ‘Man, I Feel Like a Woman’ video." She was like, “I love the sense of humor.” My favorite part of the version with her is where she does her classic banter over the guitar solo. Growing up, whenever you would hear, "Oh, so you’re Brad Pitt?" — that, to me, is Shania. It’s what she brings that no one else can bring. So for her to bring that to my song is just incredible.
How did she logistically record her verse during the pandemic?
She was in Switzerland. We just kind of mapped out where I heard her [adding a verse]. I was like, "Shania it up." She just sent me all of her vocals and then me and the producer, Jesse Frasure, sat down and sorted through everything she sent.
I hope that you get to perform it together one day.
It’s my biggest goal. When Shania headlined Stagecoach in 2017, she invited me to come out and sing "Any Man of Mine" with her. My biggest dream is to headline Stagecoach one day and have her [perform with me].
How did you meet her in the first place?
The first time we met was at the  CMT Artists of the Year event. She was getting the [artist of a lifetime] award. I remember I hadn't met her yet, but she was sitting in the front and I was singing “Peter Pan.” I looked down, and she was singing like she knew the words, and it threw me off. That, to me, was one of the first [moments of feeling like] "Oh my gosh, I think I'm making it." I got to meet her afterwards, and she was so warm and so lovely. That was the beginning of our friendship, mentor, collaborative relationship, whatever you want to call it.
You’ve always excelled at using social media to connect with your fans. How has the pandemic changed or reinforced the way you go about that?
It's the only way that I can connect with people now, so yeah, it's really forced me to go there and show what I'm doing. I'm an over-sharer. I really do put it all out there — I'm on there all the time. It's my way of seeing what people are liking, what people are doing, seeing if anyone's having a hard day. The people that have shown up to shows for six years, I know them by name. To be able to really stick with people like that is nice. I also think that as a fan, I get invested in the artist, and that's why I love the music. I know that a lot of people that listen to my music are the same way, where like they listen to what I put out because I’m putting it out.
Last question: What's your signature drink?
Other than wine, it's tequila, and if it’s tequila, it’s a margarita, and it’s probably a mezcal margarita. Those are the best.
A version of this article originally appeared in the Dec. 5, 2020 issue of Billboard.