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The year was 2000. Y2K had come and gone without a hitch. Cell phones were still a novelty and not yet an appendage. And a decidedly analog album was taking the country by storm.

The arrival of O Brother, Where Art Thou in December of that year, a soundtrack that went on to sell over eight million copies and win two Grammys (including album of the year at the 2002 awards), put a little-known label called Lost Highway on the map. Its sound — a blend of Americana, bluegrass and Appalachian standards — hit a chord. The company’s roster, which included Willie Nelson, Lyle Lovett, Lucinda Williams, Elvis Costello and eventually a 23-year-old newcomer named Kacey Musgraves, proved its vitality upon launch.

In many ways, Lost Highway was ahead of its time. It identified career artists that could thrive outside of the Nashville system and gave them the freedom to explore their own musical paths.

It’s a warm, cloudless April Saturday in Tennessee, and right now, Kacey Musgraves’ life is a Kacey Musgraves song. The singer-songwriter is driving southbound to rural Williamsport — exactly an hour from her Nashville home — where she’ll be going horseback riding and rambling along the river with a few friends.

“A good friend of mine has a beautiful farm on hundreds of acres,” she says in her Texas twang. “It’s on the Duck River, which is one of the most biologically diverse rivers in the world. It has all these specific species of things that don’t exist anywhere else. It’s really clean and beautiful, organic and peaceful. My friends and I go out there, bring a picnic and just live our best lives — barefoot, dirty, in the river. It’s so fun.”

Excursions like these have colored her songwriting on tracks like “Space Cowboy,” “Oh What a World,...