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I remember seeing Madonna’s “Don’t Tell Me” on MTV in 2000 when I was 11 years old. It was mind-blowing. Growing up in New England, country music never hit close to home. It was all Garth Brooks singing about driving a truck with a fat engine and cracking a warm beer by the lake. But Madonna took the genre and spun it on its head in one of the most transportive videos of her career: steamy cowboys and a dark ranchero vibe, mixed up with a lot of sand-strewn cheek. (It was also the first time Madonna played guitar on an album.) It’s almost hard to believe that the music video is almost 20 years old. “Don’t Tell Me” was the OG beginnings of what we are now calling the “yeehaw agenda.” Subversive twang is going mainstream in the form of Lil Nas X’s “Old Town Road,” Orville Peck’s masked exploration of masculinity in country music, and Diplo brooding in a Nudie suit on Instagram. But let me remind you that Madonna was the first to pave the way for giddy-up pop.

We begin with Madonna walking down a desert highway; an 18-wheeler truck drives by, and her cowboy hat flies off. A few seconds later, the camera zooms out, and the viewers realize that Madonna is simply walking, hips cocking side-to-side, in front of an old-timey projector. Her dancers are ever-fabulous, muscular gyrating men, characters plucked out of that Vivienne Westwood “Cowboy” T-shirt. The sound is pared back but still addictive with an ironic plucking of a guitar.

Then the fashion! Madonna’s cowboy hat is pulled down past her eyes. In the first half, she wears a simple unbuttoned plaid shirt with a bedazzled grommet belt. The dark-wash flares are stained with mud. Another look: a black leather cowboy shirt with puffed-up shoulders that reveal a slice of her belly. Her pants have chaps. Looking back at it now, the video and its wardrobe were deliciously sassy: Madonna took a good-natured country look and flipped it completely.

In the video, Madonna’s two Western outfits were made by Dsquared2, who were only making menswear at the time. “They were friends of ours, Dean and Dan [Caten], and they had yet to do anything for women,” says Phillips. “They did these incredible jeans with mud splatter with a kind of fake mud [for their men’s collection]. I asked if they would make a pair for Madonna, and they did.” The designers also provided Madonna’s “cowboy goth” look. “They also made the leather shirt, a Victorian kind of take on the cowboy shirt,” says Phillips. “That was new for the boys of Dsquared2.” That outfit appears in a pivotal moment: Once Madonna changes into it, she and her dancers let loose with a hypersexualized take on line dancing while a raccoon tail bounces from Madonna’s belt loops.

Of course, the most iconic item was Madonna’s cowboy hat. Aside from “Don’t Tell Me,” Madonna also wore it on the cover of Music and in the music video “Music,” a non-country hit. “Putting Madonna in a cowboy hat had to be tongue-in-cheek. It was something that I wanted to be short-lived. We used it in the music video, and it became this ironic prop in a way. Then her fans really grabbed on to it,” says Phillips. “I think, to this day, you can’t go to a Madonna concert without a cowboy hat.”

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