Jaime Wyatt on Finding Freedom in New Track ‘World Worth Keeping’

She may have temporarily shelved her white cowboy hat and traded her signature two-piece Western suits for a pink tracksuit, but Jaime Wyatt is just as much an outlaw as she’s ever been.

Trouble has never had a hard time finding Wyatt, 37, who spent her young life living as an old soul from a small town in Washington, only to hit rock bottom in her teenage years — hooked on drugs, strung out and crazy enough to try and rob a drug dealer.

Wyatt doesn’t shy from her past, but also refuses to be defined by the person she was 20 years ago, locked up in L.A. County jail. Today, she’s an outspoken voice for those living on the margins, an LGBT activist in living in a state she’s ready to boycott, and an evolving artist ready to challenge the conventions of country music. She’s currently doing the latter with new single “World Worth Keeping,” a roots and revival anthem celebrating an imperfect world, as well as those who make it worth keeping.

Produced by Adrian Quesada from the Black Pumas, the track is a departure from the heartbreak honky tonk kitsch of Wyatt’s 2020 record Neon Cross. The first single off her new record Feel Good, out Nov. 3 on New West Records, “World Worth Keeping” feels more like a 1960s civil rights anthem, with a timeless lyrical theme and an easy-on-the-ears sensibility highlighting Wyatts impressive range.

Wyatt sat down with Billboard earlier this year to talk about her new music, her time behind bars and the bittersweet universalism of a broken heart. Below is an edited version of that conversation.

I recently read a profile about you, and there was an interesting vignette in the piece describing a fan approaching you at your merch booth and quizzing you to see if you were outlaw country enough. Do you get approached like often?

Yeah, country has this weird thing, like, “How country are you? Are you really country?” And the answer is, “Yeah, I am.” I lived in a trailer when i was a kid in Washington. We had horses, I worked at a horse barn and my parents listened to plenty of country records. What else do you want from me?

Now that you live in Nashville, are you questioned even more?

Yeah, and some people are surprised when they find out I’m not a native Tennessean. I’m part Cherokee, and my people moved from Oklahoma to California and played in a band to support themselves. Most people in Nashville, it turns out, are really amazing, sweet compassionate people. But yeah, some people want to test me, and my response is the same — I don’t have time for it. I really just want to spend my time making music.

As a gay artist in country music, do you feel pressure to be more active pushing for LGBT representation, or do you feel pressure to not stand out?

It varies day to day. Sometimes I walk into a venue and I’m like, “I don’t want to be gay here. I don’t want to be gay today.” I’m not going to tell them who I am, not today. Other days, l play my earnest card. Usually that’s best.

Do you think artists should boycott states that push an anti-LGBT agenda.

Yes, and I live in Tennesse. But f–k it, boycott ‘em. F–king sad to say, but I was thinking about this the other day, and that’s what gets people’s attention. Not me, but someone like Taylor Swift. That’s what it would take.

What’s life like on the road for you?

Right now I’m playing with Head and the Heart. I’m playing a bunch of festivals, and mixing it up with both country bands and rock and roll. I like that type of musical exploration. We’re going out with My Morning Jacket, and I really like their music and am influenced by their stuff. Touring is like that – out on the road, every night somewhere else. We’re showing up the same time every day. It’s the most consistency that me and my musician guys have ever had in our lives.

Tell me about the new music you are working on.

I’m working with Adrian Quesada from the Black Pumas on a new record, which we recorded and produced in Austin. The music is the closest thing I’ve done to my life story so far. For me personally, it’s about falling in love while also moving and trying to get more free.

What do you mean?

Trying to feel better and trying to take care of my physical self. Trying to lighten up. It’s really more about the music than it is about the lyrics. Like, the last two records I made were very much singer-songwriter tracks hammering at different metaphors, whereas this one way is more a sound I heard in my head when we made this record.

Did you fall in love when recording the album?

Yes, but then I tumbled back out of it.

Was is it a hard fall?

No, but it hurts like it was a hard fall.

Hard fall or hard landing?

Pathetic landing, if I’m being honest.

Does it surprise you how much it hurt?

Yeah.

You want to talk about jail instead?

Yeah, that was so much easier.

Just doing your time in L.A. County Jail?

Don’t get me wrong, it was really messed up too — but I loved it in a way. There was no pressure from society to be an accountant, or even pay the bills.

That sounds a bit over-idealized.

Yeah, but anyone who has struggled with addiction can vibe on it. Jail is a f–king trip.

I read that you were arrested for robbing drug dealers?

Well, yeah, I guess. I was arrested for robbing my drug dealer, which is not that unusual. I was addicted to heroin; it was all super f–ked up.

How old were you when you got locked up?

I was 20, and turned 21 in jail. I ended up doing eight months, and then did nine and half months after that.

How did you get by?

When I first got there, I got high every day. You could use everywhere, and I was an addict — I was strung out all the time. As I started to get better, I would enjoy reading and writing little stories with different characters.

Did the experience change you?

I think I learned a lot about society, and to be honest, it made me a little jaded. Jaded on what society has for people. Where you’re born, it’s like a f–king lottery. And that’s why most people are there — not because they were born to be a criminal, but because they were born with nothing else.

Knowing what you know, do you think you would ever want kids?

It’s not the first thing that I’m looking for. I’d probably love to have an amazing Telecaster instead. Or a dog. Don’t get me wrong, kids are cool. Humans are cool. But I’m a weirdo. I gotta be out there, experiencing the world and meeting people. I always want to be connecting with other artists and recording music. With that type of lifestyle – really, my type of lifestyle – a telecaster seems more practical.