It's somehow been more than two decades since the Chicks (then known as the Dixie Chicks) released their iconic sophomore major-label studio album, Fly, on Aug. 31, 1999. The album produced an astounding eight singles, four Grammy Awards nominations, two Grammy Awards victories and some of the country trio's most iconic songs.

From "Goodbye Earl" to "Cowboy Take Me Away" to "Ready to Run," Fly is as good today as it was in 1999. To celebrate the album's anniversary, we're going back through every one of its 13 tracks, from worst to best. Read on to see how Fly shakes out:

  • 13

    "Some Days You Gotta Dance"

    “Some Days You Gotta Dance” was originally recorded in 1996 by a band called the Ranch. If you haven’t heard of them, you’ve probably heard of their most famous member: Keith Urban. The Chicks enlisted Urban to play guitar on their version of the song, which was the eighth and final single from Fly, and became a No. 7 hit.

  • 12

    "Hello Mr. Heartache"

    “Hello Mr. Heartache” is the most straightforward, down-the-middle country song on Fly. Opening with the isolated “Hello, Mr. Heartache” line, the song trades between Natalie Maines’ solo vocals and the group’s signature choral harmonies. It's not the biggest song on the album, but “Hello, Mr. Heartache” nonetheless proved that the Chicks could be as country as they wanted to be.

  • 11

    "Cold Day in July"

    “Cold Day in July” is a big, powerful and moving ballad, a song about the loneliness that comes with a breakup. “Time moves so slow when promises get broken / On this cold day in July,” its narrator explains. The Chicks’ version of “Cold Day in July” peaked at No. 10.

  • 10

    "If I Fall You're Going Down With Me"

    The melody of “If I Fall You’re Going Down With Me” is deceptively upbeat, masking lyrics that have the narrator insisting that “nobody runs from the law now, baby,” so “if I fall, you’re going down with me.” It’s not the most memorable song on Fly, but it’s still bouncy, catchy and a lot of fun.

  • 9

    "Don't Waste Your Heart"

    The verses of “Don’t Waste Your Heart” are a showcase of Maines’ clear, bright vocals. It’s a simple, mid-tempo song with a simple, bittersweet message about the need for freedom, even in love: “Don’t waste your heart on a wild thing / She’s got a soul that won’t settle on one thing / Whoa, this bird can’t sing when you’ve tied its wings / Don’t waste your heart on me.”

  • 8

    "Heartbreak Town"

    “Heartbreak Town” isn’t the only heartbreak song on Fly (the word “heartache” itself shows up in two song titles alone) -- but it is the only song about having your heart broken by a town. “Heartbreak Town,” the seventh single from Fly, is about the heartbreak that comes from trying to make it in music and in Nashville -- the titular “Heartbreak Town.” It’s not a love song in the traditional sense, but it’s still one of the most affecting songs on Fly.

  • 7

    "Let Him Fly"

    Appropriately, Fly ends with a song called “Let Him Fly.” It’s not a Chicks original, though; rather, “Let Him Fly” is a Patty Griffin cover, and its inclusion is an homage to Maines’ love of Griffin’s work. Even though it’s Griffin’s song, it’s the perfect thesis statement for the restlessness of Fly, with Maines singing, “There’s no mercy in a live wire / No rest at all in freedom / Choices we are given / It’s no choice at all.

  • 6

    "Without You"

    The stark and moody “Without You” describes the demise and fallout from the breakup of Maines’ first marriage. “Without You” wears its feelings -- and its pop influences -- on its sleeve. Listeners loved it: “Without You” is one of the two No. 1 hits from Fly.

  • 5

    "Hole in My Head"

    “Hole in My Head” rocks as hard as anything on Fly, with Maines opening the song half-growling, “Hole in my head, hole in my head / I need a boy like you like I need a hole in my head.” The song is more Americana than anything else on Fly, and with it, the Chicks prove they can pull that genre off expertly, too.

  • 4

    "Ready to Run"

    “Ready to Run” may have been the biggest song on Fly: It was the album’s lead single, a No. 2 hit, and earned Grammy nominations for Best Country Song and Best Country Performance By a Duo or Group With Vocals. The Celtic-inspired song was also featured in the movie Runaway Bride. Twenty years later, the soaring song is still one of the group's biggest, and a perennial concert staple.

  • 3

    "Sin Wagon"

    “Sin Wagon” was never officially a single, but the song became so popular that it landed at No. 52 on the Billboard charts anyway. It's a wild, frenetic romp, named for what Sandy calls Danny’s car in the movie Grease. It’s about good girls getting wild, busting stereotypes and -- most memorably -- “mattress dancing” (that's right, we said "mattress dancing"). Most of all, it’s an impossibly good time.

  • 2

    "Goodbye Earl"

    “Goodbye Earl” was one of the Chicks’ dances with controversy: Many radio stations balked at playing the song, which gleefully describes the way that two women, Mary Ann and Wanda, get murderous revenge on Wanda’s abusive husband. If that doesn’t sound like a good time, then you haven’t heard “Goodbye Earl.” It’s pure, hilarious and cathartic black comedy -- and despite the stations that wouldn’t touch it, it charted even before being released as a single, and eventually peaked at No. 13. It’s now one of the best-known and -loved songs in the Chicks’ discography.

  • 1

    "Cowboy Take Me Away"

    It’s not wild like “Sin Wagon” or darkly funny like “Goodbye Earl." “Cowboy Take Me Away” is just … good. The other No. 1 hit on Fly, “Cowboy Take Me Away” features all of the Chicks simply doing what they do best, from its unforgettable fiddle line to its memorable melody to the chorus’ powerful group harmonies. It’s not only a major hit inspired by a Calgon commercial, it’s also a song about yearning and acceptance, and it’s simply the Chicks at their absolute best.

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