The Chicks’ Groundbreaking Album ‘Fly’ Turns 25: Us Ranks All 13 Songs

The boundaries between country and pop are getting more porous by the day, but back in 1999, the lines were far more rigid — and the Chicks were at the forefront of a movement to push their genre forward.

The trio released their second major-label album, Fly , on August 31, 1999, and almost immediately changed the game. The LP debuted at No. 1 on both the Billboard 200 and Top Country albums chart, and several of their singles crossed over to the Hot 100.

While the album is full of bluegrass licks and steel guitar, traditionalist detractors felt it was too pop to be real country. Conservative critics, meanwhile, were upset by the sex-positive song “Sin Wagon” and the cheeky stomper “Goodbye Earl,” which told the story of a woman murdering her abusive husband with help from her best friend.

“Our label is so scared about ‘Sin Wagon’ because it says ‘mattress dancing,’” frontwoman Natalie Maines told Entertainment Weekly in September 1999. “They’re scared to death about that song, and they won’t talk about it in interviews. … I don’t think mattress dancing’s anything bad. I mean, my mom laughs and says, When you were 5, you were walking around singing ‘Like a Virgin.’ You know, there’s no difference, every kid grows up singing something. I’ve looked at the pop stars out there — Britney Spears and some others who have songs that are totally sexy. And I think ours is OK because we’re being tongue-in-cheek and it’s more funny; we’re not really saying, ‘Ooh baby, do it to me all night long,’ we’re joking about it.”

After the highs of 1999, the Chicks faced tons of ups and downs in their career, from CD burning to performing with Beyoncé , but Fly remains a classic, no-skips album. Keep scrolling for a ranking of all 13 tracks:

13. ‘Don’t Waste Your Heart’

As mentioned, Fly is no-skips — a quality that’s increasingly hard to come by in the era of juicing streaming numbers with extra tracks. “Don’t Waste Your Heart” is by no means bad, it’s just the weakest entry on an album full of absolute bangers.

12. ‘Some Days You Gotta Dance’

This twangy, silly bop is about the joys of shaking off your troubles by busting a move. Fun fact: It was previously recorded by Keith Urban ’s band The Ranch, and Urban plays guitar on the Chicks’ version.

11. ‘If I Fall You're Going Down With Me’

On any other album, this upbeat track would be closer to the top of the heap, but it suffers from being sandwiched between two much stronger songs: “Ready to Run” and “Cowboy Take Me Away.” Still, Martie Maguire ’s fiddle-playing and the band’s gorgeous harmonies give it a kick that makes it stick with you longer.

10. ‘Hole in My Head’

While much of Fly finds the Chicks dabbling in pop sounds, “Hole in My Head” is almost punk in nature. Make no mistake, it’s still a country song, but the electric guitar and the brassy lyrics wouldn’t sound out of place on a rock album.

9. ‘Without You’

There are so many heartbreaking ballads on this album that it’s hard to play favorites. While this one is devastating, it doesn’t hit quite as hard as what comes before and after. In true Chicks form, however, the harmonies on “Without You” are simply divine, and the full string section that comes in before the bridge will make you wonder whether you’ve ever loved anybody at all.

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8. ‘Cold Day in July’

It says something about the Chicks’ absolute dominance in the Y2K era that they released this very slow, very sad song — which is a full five minutes long — as a single, and it still charted on both the Hot 100 and Hot Country Songs. (This was also more than a decade before fans lauded Taylor Swift for dropping a 10-minute version of “All Too Well.”)

7. ‘Heartbreak Town’

Most of the sad songs on Fly are about failed relationships, but this one is about having your heart broken by a city — it tells the story of a family disappointed by their move to Nashville, which is full of “square people in a world that’s round.” The track was written by country veteran Darrell Scott , but the lyrics become extra prescient when you consider what mainstream country radio did to the Chicks after they spoke out against the Iraq War.

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6. ‘Hello Mr. Heartache’

This deep cut is perhaps the most truly country song on the album, thanks in part to steel guitar courtesy of Natalie’s dad, Lloyd Maines . No matter how many hits the Chicks chart on the Hot 100, this song proves they’ll always be Texas forever.

5. ‘Let Him Fly’

Fly ’s album closer marked the first time the Chicks’ covered a song by the great Patty Griffin , who opened for them on their 2022-2023 world tour. (They later covered “Truth No. 2” and “Top of the World” on 2002’s Home.) “Let Him Fly” is the perfect vehicle for Natalie to show off her often-underrated vocals, which start off soft and gentle before escalating to a full-throated plea.

4. ‘Ready to Run’

“Ready to Run” is one of the all-time great album openers, kicking off Fly with a burst of fiddle and tin whistle that grounds the song in the Chicks’ country roots before Natalie chimes in with some of the band’s catchiest, poppiest lyrics. The music video — a tie-in for the Julia Roberts and Richard Gere rom-com Runaway Bride — is also a delight, showing the Chicks, clad in wedding gowns, fleeing their triple wedding on bicycles.

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3. ‘Sin Wagon’

We lied about this album being no-skips, but not by choice. If you were a preteen in 1999 and in the car with your parents, then you had to skip “Sin Wagon” because of the aforementioned “mattress dancing” line. But once you took the CD back to your room, this song was perfect. Natalie scream-singing the line “one hell of a story!” The interpolation of the classic hymn “I’ll Fly Away!” That wicked fiddle breakdown (that real ones know played whenever you logged onto the Chicks’ website in that era)! If mattress dancing is wrong, then Us doesn’t want to be right.

2. ‘Cowboy Take Me Away’

This song is arguably (and rightfully) the Chicks’ biggest hit to date, full of evocative lyrics about lying “on a pillow of bluebonnets in a blanket made of stars” with your beloved. It serves as a showcase for all three women’s individual strengths: Natalie’s clarion vocals, Maguire’s spectacular fiddling and Emily Strayer ’s virtuosic banjo-playing. Additionally, the track features another stellar steel guitar moment from Natalie’s dad, Lloyd.

1. ‘Goodbye Earl’

This classic track edges out “Cowboy Take Me Away” by a nose, in part because its political message was a harbinger of what was to come for the Chicks (and other country artists, particularly female ones, who dare to speak out about racism, sexism and other societal ills). Never has a song about premeditated murder been so danceable or catchy, never has anyone imbued the phrase “black eyed peas” with so much menace. Like “Ready to Run,” this one came with an unmissable video starring Dennis Franz as the titular villain, Jane Krakowksi as Wanda and Lauren Holly as Mary-Ann.

In addition to being the kind of song you absolutely must sing along to every time you hear it, it’s had a long tail of influence on a younger generation of artists. In 2015, Swift invited Maines onstage during the 1989 gour to sing “Goodbye Earl,” and Kelsea Ballerini cited the sonag as an inspiration on her 2022 track “If You Go Down (I’m Goin’ Down Too).”