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This week, Billboard is publishing a series of lists and articles celebrating the music of 20 years ago. Our 2003 Week concludes with a look at a turning point in country music, where two smash hits daydreaming about getting away from it all helped make the beach as essential a Nashville vista as the dusty plain or the open road.

On August 25, 2012, Kenny Chesney officially declared the sovereignty of No Shoes Nation during a show at Gillette Stadium in Foxborough, Mass. A banner was eventually hung among those honoring all the Patriots’ titles to commemorate Chesney’s initial acknowledgement, though the actual origins of his fanbase’s name are shrouded in mystery (it was mentioned explicitly at least as early as a June 2012 Billboard feature on the singer).

“No Shoes Nation is more than a state of mind,” Chesney explained in the press release for his 2017 album, Live in No Shoes Nation. “It’s the place we all come together for the music, the fun and each other.” 

Whether or not you accept the legal autonomy of his shoeless (or more often, flip-flopped) fans, the decades Chesney has spent entwining country music and a specific type of geographically hazy beach vacation have fundamentally changed the genre. The tipping point came just under 20 years ago, on August 16, 2003: the No. 1 song on Billboard’s Hot Country Songs chart was Alan Jackson and Jimmy Buffett‘s “It’s Five O’Clock Somewhere,” and the No. 2 song on the chart was Kenny Chesney’s “No Shoes, No Shirt, No Problems.” Two weeks earlier, Uncle Kracker’s breezy cover of “Drift Away” (whose chorus is often misheard as “give me the Beach Boys“) reached No. 9 on the Hot 100.

America, or at least its country radio-listening contingent, needed a break — and it hasn’t put down its margaritas (or put on its shoes) since Chesney and Jackson spent one sweaty, sunburned summer compelling country listeners to trade back roads for sand bars. Etching a new country radio formula in stone and inspiring hundreds of imitators, they also ensured some of their songs’ questionable, touristic language and imagery stayed in the genre’s canon.

Before No Shoes Nation established its borders, of course, there was the little hamlet of Margaritaville. The early-’00s beach country renaissance arrived about a quarter-century after Buffett — having flopped pretty hard trying to ride the coattails of the Texas outlaws into Nashville — carved out what would become a billion-dollar niche romanticizing the then-untamed Key West waterfront. Buffett, having grown up on the less-scenic Gulf shores of Mobile, Alabama, had some claim to the island-time lifestyle that he would brand so effectively. 

His conversion experience, though, came courtesy of singer-songwriter Jerry Jeff Walker, who Buffett had met while trying to make it in Nashville. Walker, who lived in Miami at the time, led a down-on-his-luck Buffett around south Florida in typical vagabond fashion. Buffett fell in love with Key West, and told Walker to leave him there when he headed back to Miami. “I’d been a teenager on Bourbon Street in college, I knew New Orleans from childhood, and Key West just had that magic,” Buffett later told Texas Monthly. 

After “Margaritaville” hit No. 8 on the Billboard Hot 100 in 1977 — marking the singer-songwriter’s first, and still biggest, solo hit — Buffett was more than content to lean all the way into the light subversion of his beach-bum persona. With it, he was able to top the Adult Contemporary Airplay chart and reach No. 13 on Hot Country Songs, expanding his audience outside of Nashville by translating hippie nonchalance into a mode that even good hard-working folks could understand: a beach vacation. 

There is an actual self-deprecating critique buried in “Margaritaville”: Buffett describes it as “wasting away,” after all, and a “lost” third verse observes tourists who “dream about weight loss” and “wish they could be their own boss” (tourists who sound a lot like most people listening to “Margaritaville”). But any reflection on what it might mean to actually escape the drudgery that makes frozen beverages so symbolic and seductive was clearly eclipsed by the fun of singing about margaritas. 

Having forged a new sunny, breezy bridge between country music and pop — one that would eventually be coined “gulf and western” — Jimmy Buffett more or less played for the Parrotheads and explored different Margaritaville-themed ventures for the next 20 years. He never came close to the pop ubiquity he found with “Margaritaville” — until 2003, that is, when his unlikely compatriot Alan Jackson wondered, “What would Jimmy Buffett do?”

Jackson, who made his name through the ’90s as the most agreeable kind of neo-traditional country singer-songwriter, isn’t the kind of artist one would typically associate with “beach country” — even post-“Somewhere.” But the Georgia native claimed Buffett as an influence prior to their most familiar collaboration — his 1992 signature song “Chattahoochee” is about frolicking around a body of water, after all. “I’ve always been a big Jimmy Buffett fan,” Jackson wrote in the liner notes for his 1999 album Under The Influence, which included his first collaboration with Buffett on a cover of “Margaritaville.” “I like his music and the fact that he does what he wants to do.” (Billboard called the cover “a bit jarring.”)

In spite of the surprise that greeted his “Margaritaville” cover, Jackson went looking for another good duet option for him and Buffett — and came up with the most successful single of his career with “It’s Five O’Clock Somewhere.” “When I got the song it sounded like Buffett, so I called him up and asked him if he’d do it with me,” Jackson told the AP in 2003. “We cut the track in Nashville, then I flew to Key West and did the vocals [at Buffett’s Shrimp Boat Studio].” Buffett was not enormously invested in the song: he didn’t go to the video shoot (hence the live interlude), nor did he talk to the press at all about it as it skyrocketed up the charts — and it made no difference whatsoever. The song became not just one of the biggest of the year, spending eight weeks atop the country charts, but of the decade, a timeless drinking anthem that’s more about imagining a carefree beach vacation than actually getting to go on one.

Chesney first publicly embraced Buffett a little earlier than Jackson, with the late 1998 release of his breakthrough hit “How Forever Feels.” The singer-songwriter, raised in a small town near Knoxville, had as solid of country music bona fides as anyone in Nashville. But they hadn’t helped him break away from the pack of nearly indistinguishable mid-’90s cowboy-hatted young men attempting to replicate Garth Brooks’ success. “How Forever Feels,” which spent six weeks atop the Hot Country Songs chart, was the reason people started to learn his name. 

The song, which was written by Wendell Mobley and Tony Mullins, has a decidedly country aesthetic — fiddle, pedal steel and all — and is about a decidedly country topic (marriage). But it opens with a little tribute to Buffett: “Big orange ball, sinkin’ in the water/ Toes in the sand, couldn’t get much hotter…Now I know how Jimmy Buffett feels.” That, along with a video shot on a picturesque St. Thomas beach in which Chesney alternates between his Brooksian black cowboy hat and a backwards baseball hat and sunglasses, was enough to cement his brand as “beach guy.” As “Forever” climbed the Billboard charts, Chesney added a cover of “Margaritaville” to his own set, and started tossing beach balls into the crowd when he played his single. (Earlier in 1998, Garth himself also scored a Buffett-influenced hit of his own, with the land-weary “Two Pina Coladas.”)

It didn’t really matter that “She Thinks My Tractor’s Sexy” and any number of other non-explicitly “beach” songs became hits for Chesney soon after — his fate was cast with his first mention of “oil tannin’ señoritas.” “Before I was just in a big bowl of guys,” Chesney told the AP in 2004. “You’ve got to find your avenue, your way to separate yourself. I think for the first time in my career I was able to pull myself out of that ditch and be known as more than just a country hat act who was singing the same old songs everybody else was singing.”

Seemingly disinterested in messing with success, Chesney and his team put out a greatest hits compilation in 2000 that featured the first of several iconic country-beach-kitsch album covers. Chesney, fully clothed in a black cowboy hat and white button-down shirt, is pictured emerging from the ocean — despite the fact that only one of the included songs even mentioned the beach (on the back, he was similarly submerged while wearing overalls). The album became his first to top the Country Albums chart, and has since gone platinum five times over.

Releasing No Shoes, No Shirt, No Problems in 2002, then, was almost like playing with house money for the Chesney camp. The album followed a now-familiar formula: a couple overtly beachy tunes, combined with a slew of more familiar country radio sounds (and a Bruce Springsteen cover, lest anyone question his range, or right to integrate rock elements into his performances at bigger and bigger venues). The cover featured Chesney in a black tank top and seemingly impractical cowboy hat on the sand, so that you knew his latitude and attitude before even listening to the album.

Surprisingly, the title track — Chesney’s most overtly island-themed tune to date (note the ukulele) — was No Problems‘ final single. “The islands,” Chesney intones during the video’s opening monologue. “They’re the one place where you can truly be as you are — where it doesn’t matter what you’ve done or how you make your life, you’re just there, with the sun, the sand, the sea, and the locals.” In place of Buffett’s hazy pairing of self-indulgence and deprecation, Chesney offers a manifesto. (Chesney had actually passed “It’s Five O’Clock Somewhere,” which was originally offered to him by writers Don Rollins and Jim “Moose” Brown before Jackson snapped it up.)

Together, “Somewhere” and “No Problems” distill how Chesney and Jackson helped retool Buffett’s beachy bohemia into a core element of contemporary country music — how they translated its hippie dropout energy into something that fit easily within the world of Nashville’s moralized conservatism. 

“Beach bum” is not a lifestyle for either, but an escape from the unpleasant but necessary rigors of doing one’s job: “I’m gettin’ paid by the hour and older by the minute, my boss just pushed me over the limit,” Jackson sings, “I’d like to call him something; I think I’ll just call it a day.” In place of Johnny Paycheck’s “Take This Job and Shove It,” we get an anthem for taking this job and swallowing it…in the form of a tasty frozen beverage. Chesney has been “working six days a week,” while Jackson hasn’t “had a day off now in over a year” — they’ve earned this indulgence, which could hardly be deemed anything close to “wastin’ away.”

The darker side of all three artists’ take on coastal escapes comes with a relentlessly casual attitude towards “locals,” as Chesney calls them in the aforementioned monologue, treating them like an unchanging, natural, impersonal force – akin to the sun, the sand and the sea. Most often, the beachy escapes imagined in “Somewhere,” “No Problems” and the dozens of copycats since are uninhabited except for sexy nameless “senoritas;” they have no issue, then, with somewhat hackneyed countrified takes on reggae and calypso. 

In these songs, there is a clear sense that the intended audience is people who view Mexico or Jamaica as a place to vacation, not as their home — and those listeners seem to feel entitled to those beaches and margaritas, regardless of the potential consequences of their perpetual visits for their inhabitants. Margaritaville resorts stretch throughout the Caribbean and Central America and press uncomfortably up against the residents of those actual countries where people live all year long.

Chesney released “When The Sun Goes Down,” a beachy duet with Uncle Kracker, in 2004 — the first of many attempts to follow up “No Problems.” Buffett would lean into his way-belated Nashville success the following year with an album of country collaborations called License to Chill, often quipping about getting his first country No. 1 and his first award (the CMA for Vocal Event of the Year) long after becoming a household name. “I was thinking of doing a record like this for a long time,” Buffett told the Boston Globe at the time. “It certainly has not gone unnoticed by me that I was either getting mentioned as an influence or was included in song lyrics by a lot of country singers.” 

“I think everybody’s a Jimmy Buffett wannabe,” Chesney said in an interview with the Minneapolis Star-Tribune in 2005. “Deep down, Jimmy was always a country artist. His songs had a country soul to them.” 

Now, it’s the rare country album that doesn’t have some sort of vacation-themed song or allusion to mix up the drinking tunes, whether it’s Dierks Bentley’s “Somewhere on a Beach,” Morgan Wallen’s “Sand In My Boots,” or Luke Combs going “deep sea señorita fishing down in Panama.” The Buffett aesthetic and ethos was, via Chesney and Jackson, turned into yet another familiar Music Row formula; a theme that allows for No Shoes Nation to treat a concert like a more affordable version of the kinds of vacations they’re singing along to songs about from the Sandbar (what Chesney tours call the pit). 

“You can call him a Kmart Buffett all you want, but give Chesney credit,” as Sean Daly put it in the St. Petersburg Times. “He’s coupled boat-drink dreams with blue-collar reality, a simple formula with staggering 21st century pull.”

While Jackson, ever a traditionalist, hasn’t done much with his beachy cred, Chesney has maintained all along that his ever-growing vacation anthem oeuvre is about more than just him keeping a good thing going. 

“The people who believe this is all an invention of clever marketing have missed the point,” he told Billboard in 2007. “Not that there hasn’t been some great marketing, but … we don’t put a check out there I can’t cash. When people talk about the tropical lifestyle, the beach, summer, friends, we absolutely put that out there…But we didn’t just pull it out of the air. That’s my life and how I live.” If the country charts of the past two decades are any indication, more and more country fans wish they could live that way too.