Country singer-songwriter Caroline Jones has crisscrossed the country on tours with Kenny Chesney, Zac Brown and Jimmy Buffett, seeing bits here and there out of the bus window, yet she’s never been on a true coast-to-coast road trip. So when planning for the fictional car chase that takes place over two music videos for her songs “The Difference” and “Chasin’ Me,” she left no stone unturned.

The chase has actor Cody Walker—the brother of the late Paul Walker (“The Fast and the Furious”) pursuing the Connecticut-raised singer-songwriter in classic cars from the Florida Keys to Big Sur, bouncing around through the South, Memphis and Zion National Park in Utah, among other places.

“We knew we wanted to end up on the Pacific Ocean, and there’s a few different ways to route that,” said Jones, the daughter of well-known billionaire hedge fund manager Paul Tudor Jones II. “We spent months planning the music videos. It was a huge undertaking. But it was so fun. … We just wanted to find the prettiest place on the Pacific Ocean that made sense from Zion, and we didn’t really want to do the L.A. thing. We just thought the Big Sur was the most cinematic and beautiful place that we could end the video, and I’m so happy with how it turned out.”

Both songs are from Jones’ 2019 EP, Chasin’ Me. The two videos tell a love story mirrored in the lyrics to “Chasin’ Me” of the singer at first resisting a man’s advances before falling for him.

“That was so fun to develop a story [about] how you build trust and how you navigate literally and figuratively down a path of romance,” she said. “That was really fun to use as a metaphor, and the cars are super cool, especially for car nerds.”

Jones wrote four of the six tracks on Chasin’ Me by herself. Current single “All of the Boys” was a co-write with Zac Brown, while “Gulf Coast Girl” was written for her by Jimmy Buffett and Mac McAnally and includes guest appearances by Chesney and Lukas Nelson. She counts them as mentors. She co-produced the record with Ric Wake (Mariah Carey, Celine Dion, Whitney Houston), who’s also her manager.

Jones has been writing songs since she was 10, but country music wasn’t on her radar until she was 17. At New York University, she studied creative writing and learned to sing opera and jazz, as well as play various instruments like piano, guitar, banjo, mandolin and harmonica. Between 2010 and 2012 she released several albums independently.

She was introduced to Chesney at a hurricane benefit concert in 2017. Since then, she’s also opened for Tim McGraw and Faith Hill. In 2018, she released Bare Feet, her first LP. On the album, she played every instrument other than bass and drums. She’s opened for Zac Brown Band on its last three summer tours. Outside of playing music, she’s also hosted Sirius XM’s Art & Soul program, where she interviews other artists.

Jones was set to have a busy 2020. She started the year with Lee Brice and Sara Evans, played at the Grand Ole Opry stage and released a remix EP of “All of the Boys,” her current single, with a dance mix, coffee house mix and country mix. Then coronavirus arrived, and Jones began sheltering in place at her home in South Florida, with bright pink bougainvillea outside her window. Instead, she plans on releasing several singles this summer, eventually leading to an album release.

RIFF: You’re from Connecticut but were brought up in New York? Then where does Florida come into the picture?

Caroline Jones: Well, about five years ago this summer, I first met and partnered with my current manager and co-producer Ric Wake. …. And he had a studio down in Florida, and his production team engineer and assistant engineer was based in Florida. I was supposed to come down for two weeks to record some songs, and I never left. I fell in love with it. I fell in love with the team. Ric and I hit it off immediately. We recorded the entirety of … Bare Feet down here. Now I split my time between Florida and Nashville. … My band is more based in Nashville, and my recording team is based down here. I love both places.

You studied opera and jazz singing, and you’re from Connecticut, so naturally you’re attracted to country music?

I did not grow up listening to country. I grew up listening to a lot of classic rock, R&B, and great vocalists of the ‘90s. I like ‘70s and ‘80s pop. I fell in love with country inadvertently through my songwriting. I’ve been writing songs since I was 10, 11 years old, and I just kind of naturally have singer-songwriter country sensibilities in my music that my manager at the time picked up on and suggested that I travel to Nashville and get a feel for the songwriting community there. So I did, and I went to a show at the Bluebird Cafe, which is a legendary singer-songwriter venue. And I just fell in love with it.

I was just transfixed, and it felt like I found the missing piece of my artistry. I felt like I found a tribe of people who had the same musical values that I did, and I just really enjoyed delving all the way back to the Carter family and Hank Williams and … the whole lineage of country music … like as an exercise in music education, just by way of being a fangirl.

I have lots of different influences in my music, which is wonderful to see in this generation. This is one of the first generations where you can hear all different genres and music because of globalization. In previous generations, you had people in middle America who listen to country music, and you had people in cities who listen to jazz, or you had people in the Deep South who listen to blues music, so it was much more geographically driven. And now everyone grows up listening to everything, so you’re starting to see a lot more crossover. It’s really cool, I think.

How did you go from meeting Jimmy Buffet at the hurricane relief show to him taking you under his wing?

Fortunately, and kind of amazingly, it was pretty immediate. We just really hit it off, and he just went out of his way from the beginning to be extremely hospitable and extremely supportive of me. … The first night I met him, I went up and sang like three or four songs with him on stage; he was just that generous with his stage time. I got to close the frickin’ show that had Kenny Chesney, Jake Owen and Toby Keith on it. … I’d like to think that he saw some shared values in me and a shared drive, and he just has mentored me ever since.

And how did you get to know Zac Brown and Kenny Chesney?

I met Kenny the same night I met Jimmy. So Kenny was playing that show, and he was kind enough to invite me onto the bus and talk to me and mentor me, find out how I was doing and support me. You have to remember these guys are just like the top-caliber of artists, entertainers and humans. This is not like normal stuff, so I don’t take it for granted.

It is a really beautiful lost art; mentorship. It’s so important in any industry to have mentors who are more experienced than you, with the same dream, take you under their wing. It’s invaluable. You can’t even put a price on it. …

I met Zac before all these people … through a friend of a friend who played him my music, and he reached out and invited me to open two shows for him. I ended up opening the whole tour, and that was my first huge tour. That was my first time experiencing crowds of 25 to 30,000 people. I just thought I’d died and gone to heaven. I’ve been dreaming about that for so many years before I got to do it, touring on that level. Being an opening act; I know not everyone likes it, but it’s so much fun. It’s like summer camp, and Zac Brown or Kenny Chesney is your counselor. It’s so exciting. I miss it. You’re making me miss it because when I think about it, I just get so excited.

Zac Brown’s a country artist who can pivot quickly to a cover of Dave Matthews’ “Ants Marching” or Metallica’s “Enter Sandman.” Do you look to him as an example of a country artist spreading his wings to other genres?

Absolutely. It’s not so much like trying consciously to spread your wings. It’s just really natural and fun. It’s much more unnatural to put yourself in a box when you’re an artist because you’re just always evolving and excited by so many different things, and Zac is fearless like that.

In what ways have your mom and dad helped you in your music career?

My dad’s musical taste is very different than mine. He actually has a pretty good ear for someone who’s not musical. He really enjoys production. He enjoys Big Band instrumentation and loves The Temptations, Earth, Wind and Fire and all the Motown, Stax stuff—those big soul bands, which is not exactly my thing. So it’s really cool to get his perspective. He’s not super musical, but he loves to be able to sing along to things. My mom is much more vocally driven. We grew up singing along to Mariah Carey and Celine Dion. She’s much more of a vocalist fan.

They’ve influenced my music career and my taste in that way, I guess. I’m very blessed to have really supportive parents. Even if they don’t agree with every turn that I’ve taken on the path that I’ve chosen, they always support me, and that’s really special.

Your family has had a lot of success in a different field because of your father and also his family. Are there any disadvantages to making it in the music industry when coming from a family like yours? In previous interviews, your dad said he encouraged you and your siblings to go into trading. When did you decide you were more interested in making music?

The most honest way I can respond to that is that there’s only really ever been support and love from my family. That’s the biggest gift that I’ve gotten from my family, and charting your own path in any field is always a challenge and a beautiful thing, but it’s worth it when it’s your dream.

You write most of your own songs. That’s unique for Nashville. Why do you prefer to work on your own?

I’m open to collaboration more and more as I mature as an artist. I was really intent on homing in on and alchemizing my own style, and I still am. I’m a staunch individualist. I love pushing myself to see how far my creativity can take me. So the collaboration has been a little slower to evolve, but I don’t regret that, because that’s how we build our craft. As a songwriter, you have to have an identity as an artist, and that takes time to build. If you are constantly looking outside of yourself and listening to outside influences, it’s harder to build that.

Some of my favorite songwriters write by themselves: Bob Dylan, Lori McKenna; Taylor Swift writes incredibly well by herself. I think that’s a real lost art sometimes because the co-writing culture in Nashville is so strong, and there’s such incredible co-writers, unbelievable talent. So I think a balance, for me, is healthy.

How did you come to have Paul Walker’s brother appear in the videos to “The Difference” and “Chasin’ Me?”

Originally, we wanted a race car driver, like one of the Indy guys. I didn’t end up getting one, and I’m so glad because, first of all, it just wasn’t necessary, and we weren’t going that fast. And second of all, Cody’s an actor, among many other things. He’s very multi-talented. It was one of those things that was meant to be. He was such a team player, such a nice guy. Such a talent. He couldn’t have been better to work with. I’m really grateful.

Follow editor Roman Gokhman at Twitter.com/RomiTheWriter.