When Jimmy Buffett passed away on Sept. 1, 2023 at age 76, the decorated singer/songwriter, performer, author and entrepreneur left behind a legacy that unified a swath of musical genres and people.

The man behind "Margaritaville" — the song and later the brand — and so many other tunes that bridged folk sensibilities with country and rock touches, sometimes called "Gulf & Western," was much more than the beach-obsessed character he played in song. Although he had plenty of industry successes, notching 13 Billboard Hot 100 hits, a pair of GRAMMY Award nominations, while selling more than 20 million albums, his fans loved him for how he made them feel.

In song, he was a true storyteller that was clever, funny and introspective; in performances, he was the quintessential Parrothead to the core. As the ringleader of the party, he was generous enough to share the spotlight with members of his Coral Reefer Band as well as the fans who dressed up, tailgated outside the venues and spread their joy to others.

Both sides of Buffett were crucial building blocks in the business empire he built around his persona as the laid-back, casually philosophical beach bum. The Margaritaville restaurant and resort chains, his Landshark Lager beer and many other ventures made him a billionaire, while his storytelling prowess made him one of few authors to top both fiction and nonfiction bestsellers' lists. While his legacy may be both musical and merchandisable, the endearing qualities of the Parrothead personality he created is the real reward for his fans.

Below, remember Buffett's illustrious career through 15 classic songs — just a glimpse of his genius that made it okay for country singers to loosen up, for rockers to pick up an acoustic guitar, and for the Parrotheads to while away their days in the sun.

While Buffett's first two albums showed glimpses of the celebrated artist he would become, his songwriting largely hewed close to the earnest observations typical of early-seventies folkies. By his third album, though, he had grown into his winking style of satire and breezy, Nashville-meets-Key West flair.

This cut from A White Sports Coat and a Pink Crustacean combined both, and created the template for hundreds of bleary-eyed sing-alongs to follow. "The Great Filling Station Hold-Up" may have been the proper album single, but "Why Don't We Get Drunk," its controversial B-side, became the bigger tune — and the one featured on his seven-times Platinum compilation, Songs You Know By Heart.

As Buffett pulled away from his folk sensibilities, Nashville-style balladry became a big part of his sound. "Come Monday"  brings orchestral strings into the mix to help express the yearnings he felt while stuck in "a brown L.A. haze," pining for his love back home. The song resonated with new fans, becoming his first Top 40 single, as it peaked at No. 30 on the Billboard Hot 100.

"A Pirate Looks at Forty," 'A1A' (1974)

It probably wasn't a stretch for Buffett to sing so convincingly from the perspective of a seafaring, modern-day pirate. He considered his own later entrepreneurial forays an adventure on the high seas of life. But back in '74, he was so inspired by the real-life stories of a Key West smuggler and rapscallion he befriended that he wrote "A Pirate Looks at Forty" from his perspective. 

A key cut on his second long-player of '74, A1A, "Pirate" is empathetic to the dashed dreams and yearnings of a man looking back at his wins and losses. And despite the eventual billionaire fortunes of Buffett himself, his narrator determines the balance is a draw.

Buffett's next album, Changes in Latitude, Changes in Attitude, launched his music career into the stratosphere — and its success had a lot to do with "Margaritaville," a Top 10 hit and the basis of the global brand he later built.

Essentially, "Margaritaville" established the beach-boho lifestyle as an aspiration for millions. Against a backdrop of tropical instruments like steel drum and marimba, Buffett sang of the quiet pleasures of an unhurried life, unconcerned with the tides and buoyed by his favorite blender drink. In 2016, the tune was voted into the GRAMMY Hall of Fame, while the Library of Congress added it to the National Recording Registry in April 2023. 

"Son Of A Son Of A Sailor," 'Son Of A Son Of A Sailor' (1978)

Whether Buffett's soft and breezy music can be considered "yacht rock" is a subject of debate, but he certainly rocked a yacht or two in his day — and he dressed the part for the cover of his album Son Of A Son Of A Sailor. The title track is a definitive take on his love of the wandering life, untethered from the anchors many cling to and always in search of the next port of call. A master of ballads whimsical and wistful, Buffett manages to be both at once here.

Before it was a menu item at his Margaritaville-branded restaurants and resorts, "Cheeseburger in Paradise" was a mirage Buffett dreamed about while marooned at sea. As the story goes, a misadventure in the Caribbean left Buffett with only meager rations to survive. And when he finally struck a landing on dry ground, his first meal inspired one of his most enduring songs: an easy-rockin' Top 40 hit about cheeseburgers that somehow isn't a novelty cut — a hat trick only Buffett could pull off.

"Fins," 'Volcano' (1979)

As the lead tune from his 11th album, Volcano, "Fins" entered the pantheon of Buffett concert staples immediately and helped inspire plenty of Parrothead ephemera, as well as the title of the 1990 live album Feeding Frenzy and his Landshark Lager brand. But none of that would be important if not for Buffett's song about a hapless woman who travels to the beach to relax, but instead is encircled by "sharks that can swim on the land." With "fins" to the left and right of her, she's "the only bait in town."

Buffett had a knack for coining phrases — and "Boat Drinks" certainly qualifies among the best. What makes a boat ride better? Boat drinks, of course.

An album cut from Volcano (also featured as a B-side to the single "Survive"), Buffett ironically wrote the song while on a winter sojourn in Boston, exiled from his native habitat and wishing the city's fresh blanket of snow were the sugar-white sands of Florida. Musically, the tune is a quintessential cut from his whirlwind late-seventies period, when Caribbean themes and sonic textures became his calling card.

"It's My Job," 'Coconut Telegraph' (1981)

Long before Mac McAnally joined Buffett as a sideman in the Coral Reefer Band, Buffett sent the young artist a note praising his songwriting. Then, for his 1981 album, Coconut Telegraph, Buffett boosted his new friend's fortunes by recording "It's My Job," a tune McAnally wrote about taking pride in your work — however menial or miserable it may be — while working on a hot Mississippi highway in the summertime. The tune reached No. 57 on the Billboard Hot 100, marking Buffett's last appearance on the chart until 2003 (more on that later).

The 1980s were the beginning of Buffett's transition from chart champion to blockbuster concert draw. But he still had plenty of gas in the songwriting tank, as songs like "One Particular Harbor" proved.

Inspired by his travels in Polynesia, Buffett sings in Tahitian about the "abundance of the sea" after leaving behind the mainland. While the song was a minor hit on Adult Contemporary radio, it became a fan favorite and a mainstay of live shows from the era. 

"Jamaica Mistaica," 'Banana Wind' (1996)

Like on "Cheeseburger in Paradise," Buffett's penchant for seeing the humor in the unfortunate dustups of his real life shines on the Banana Wind cut "Jamaica Mistaica." In this case, Jamaican police opened fire on his plane, believing he was a smuggler or criminal straight out of his own song "A Pirate Looks at Forty." Set to a reggae beat, though, Buffett lets listeners in on the joke — an endearing quality that earned him the love not only of Parrotheads, but also an official apology from the Jamaican government.

By the dawn of the new century, Buffett's beach-bum aesthetic had conquered Nashville, the town he left in the early '70s to find his identity as an artist in Key West. And "It's Five O'Clock Somewhere," recorded with country star Alan Jackson and featured on his Greatest Hits Volume II, was exactly the new Buffett-style anthem Music City needed.

It was also what Buffett's 21st century career needed: "It's Five O'Clock Somewhere" earned the veteran singer his first No. 1 on Billboard's Hot Country Songs chart as well as his first GRAMMY nomination (in the Best Country Collaboration With Vocals Category) and his first Country Music Association Award (for Vocal Event of the Year). Later, the song notched the No. 3 song of the decade on Billboard's Hot Country Songs chart, proving Buffett's staying power amid shifting musical trends.

"Bama Breeze," 'Take the Weather With You' (2006)

After Hurricane Katrina made matchsticks of Buffett's home territory in 2005 — the beachfront bars of Mississippi, Alabama and Florida where he cut his teeth — he responded with the album Take the Weather With You and its leadoff track, "Bama Breeze." The country-rock tune extols the virtues of the so-called "Redneck Riviera" and coming of age as the sun came up outside the dive bars of the Gulf Coast, many of which were now ruined. The song also nods to the fans who have stuck by him since the beginning: "At the Bama Breeze, you're one of our own down there/ You'll never drink alone down there/ Good god, I feel at home down there."

One of the most rewarding markers of a mature career in music is the respect paid by each successive generation of musicians. Newly minted country star Zac Brown paid homage with "Knee Deep," which was written with Buffett in mind and borrows heavily from his long-established beachbound, escape-by-tropics aesthetic. But it truly takes off when Buffett himself takes the second verse and then harmonizes the choruses with Brown. And the combination proved sweet for both acts: the song was certified triple Platinum and landed at No. 1 on Billboard's Hot Country Songs and Country Airplay charts.

Although the public wasn't aware at the time, Buffett was dealing with the effects of Merkel cell carcinoma — the disease that claimed his life — throughout his final years of touring and recording music. Released two months after he passed, Equal Strain On All Parts, his 32nd and final album, arrived like a comforting voice from beyond to Parrotheads and casual fans alike.

On "Bubbles Up," Buffett was in a particularly reflective mood, facing his own mortality in his most measured, reassuring manner. The title phrase came from his survival training — if he were to find himself submerged in water, either from a boat or plane wreck, his trainers advised him to follow the bubbles up to the surface. "They will always point you toward home," he sings, "no matter how deep or how far you roam." 

For a songwriter and performer who spent his life showing the world how to relax, enjoy life and see the humor in life's challenges, the reassuring sentiment — to quote the title of his 2004 album — underscores that a License to Chill has no expiration date.