On Aug. 31, 1999, the Dixie Chicks released their second major-label album, Fly. The album, which was also their second one recorded with Natalie Maines in the lineup, built on the success of 1998's Wide Open Spaces.

Fly spawned a staggering eight country radio singles. Even more impressive is the fact that six of those songs made the Top 10 and two -- "Without You" and "Cowboy Take Me Away" -- hit No. 1. Only "Heartbreak Town," which peaked at No. 23, and, surprisingly enough, "Goodbye Earl," which landed at No. 13, missed the mark. However, the latter song became the Dixie Chicks' first huge U.S. pop crossover hit, as it reached No. 19 on the Billboard Hot 100.

"Goodbye Earl" is in the grand tradition of twisted country tunes, as it focuses on best friends Mary Anne and Wanda, who conspire to kill the latter's no-good, abusive husband, Earl, and then live happily ever after without him. The Dixie Chicks amplify the black comedy intrinsic to the song's lyrics by pairing it with upbeat music brimming with perky "na-na-na"s and cheerful banjo.

The song embodies a major theme on Fly: Its main characters are frequently self-assured women who aren't afraid to strike out on their own. That's also the case with "Ready to Run," a song that hit No. 2, which is all about a bride getting cold feet about committing to a long-term relationship, much less marriage: "All I'm ready to do is have some fun / What's all this talk about love?"

Sony

"Cowboy Take Me Away," meanwhile, just might be the quintessential Dixie Chicks song, at least musically: Martie Maguire's keening fiddle intertwines seamlessly with Emily Strayer's understated banjo as Maines sings deeply romantic lyrics about finding comfort and solace in a perfect guy, here idealized as a no-frills cowboy.

On Fly, the group wrote or co-wrote multiple song -- in fact, Strayer and Maines handled the fierce "Don't Waste Your Heart" themselves -- but also cut tunes written by notable songwriters, including Patty Griffin ("Let Her Fly"), Jim Lauderdale and Buddy Miller ("Hole in My Head"), and Darrell Scott ("Heartbreak Town"). The Dixie Chicks even recorded "Some Days You Gotta Dance," which was originally cut by Keith Urban's early band the Ranch. (In a nice favor-return, Urban appears on the Chicks' take.)

However, Fly illustrates just how unique the group's approach to country music was, what with their nods to bluegrass, pop, Americana and folk. "I just feel like any song we write or song that's given to us, we need to put our own stamp on it, and it doesn't really come to life until we three sit around with a guitar and a fiddle and a banjo or a dobro and make it our own," Maguire says in an interview disc. "So when songwriters try to make their demos sound what they think 'Chickish' is, we tend to not be drawn to those songs."

As with Wide Open Spaces, Fly was certified diamond by the RIAA, which signifies 10 million albums shipped. In the wake of this success, the Dixie Chicks won two Grammy Awards: Best Country Performance By a Duo or Group With Vocal for "Ready to Run" and Best Country Album.

Fly's commercial performance also caused the group to take a second look at their relationship with their record label. In 2001, the Dixie Chicks sued Sony for $4 million on the grounds of "systematic thievery" amid accusations that the band didn't receive all of the royalties they deserved for Wide Open Spaces and Fly. The lawsuit was settled out of court.

Fly + 19 More Country Albums Turning 20 in 2019