In 1999, the same year the Chicks released one of the best-selling country albums of all time, the group joined a tour that, at the time, seemed as far removed from mainstream Nashville as possible: the Lilith Fair. Equipped with banjos, mandolins, twangy harmonies, and some (then-controversial) crop tops, the trio of Natalie Maines, Emily Strayer, and Martie Maguire—then known as the Dixie Chicks—played nearly 20 dates on the all-female tour. It was proof that the Chicks’ music—and the women who made it—had transcended the limits of country music culture. And the higher the Chicks rose, the clearer it became that Maines, Strayer, and Maguire weren’t following anyone’s rules but their own. The beauty of Fly—the band’s chart-topping, Grammy-winning 1999 smash—is that, despite the album’s mischievous spirit, it’s a country record to its core: Polished and produced, to be sure, but also overflowing with ace instrumentation and strings that were more traditional (at least compared to the genre-wandering music of late-1990s pop-crossover acts like Shania Twain). Fly also demonstrated that the members of the Chicks were more than exemplary players and singers; they could write, too. The trio had a hand in five of the album’s songs, including the classic, sweeping love song “Cowboy Take Me Away.” Written for Maguire’s husband at the time, it’s not so much a pledge of everlasting commitment as it is an ode to the freedom that comes with his nomadic, unfettered lifestyle. “Fly this girl as high as you can,” Maines sings, “into the wild blue.” And fly they do, on an album that includes tributes to rebellious women, including “Sin Wagon” and the now-infamous murder ballad “Goodbye Earl”—both of which caused shocked country music programmers and DJs to pull out their hair. The response to some of Fly’s more boundary-pushing material forced listeners to confront their biases: After all, country music’s men had always sung about sexual appetites—Conway Twitty’s “Slow Hand,” anyone?—yet Nashville let out a collective shudder when such desires were seen through a female perspective. Murder ballads, meanwhile, were a downright country tradition—so why such outrage about a song in which the woman is the guilty party? Maybe, as Maines sang, it’s because Earl deserved it. But the Nashville lifers who found these songs so troublesome were far outnumbered by the Chicks’ ever-expanding fanbase—and even now, decades after its release, the appeal and influence of Fly endures. The album created a road map for future artists like Taylor Swift and Maren Morris, proving female country musicians could dress how they desired, sing the stories they wanted to tell, and defy the genre’s expectations—and, most importantly, that they could truly fly.

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