With his crinkled smile, breezy tunes and barefoot stage presence, Jimmy Buffett encompassed the persona of a beach bum.

But a 50-plus year recording career that spawned unparalleled devotion from fans as well as branded restaurants, books, beer, resorts, a Broadway show and cruise line established Buffett as a bona fide mogul.

The “Margaritaville” icon died Friday, according to a statement on his official website and social media pages. He was 76.

The statement reads the singer died "peacefully ... surrounded by his family, friends, music and dogs."

"He lived his life like a song till the very last breath and will be missed beyond measure by so many."

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Buffett struggled with an undisclosed health issue starting in 2022, when he was hospitalized and forced to cancel several shows. In May and June 2023, he canceled more concerts after revealing he was “back in the hospital to address some issues that needed immediate attention.”

It was a striking admission from the road warrior, whose summer tours attracted swarms of devotees, known as Parrotheads. His fan base is legendary, with hundreds of Parrothead Club chapters around the country whose members trekked to multiple concerts adorned in Hawaiian shirts and hats bearing the tropical motif of Buffett’s songs.

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Along with his 1977 breakthrough “Margaritaville,” the languid ode to relaxation with a buzzy bent that was submitted to the National Recording Registry in 2023, Buffett penned a bonanza of pop culture staples in the 1970s and 1980s.

“Come Monday,” “Cheeseburger in Paradise,” “Changes in Latitudes, Changes in Attitudes,” “A Pirate Looks at Forty” and “Pencil Thin Mustache” were alternately contemplative and silly. But all bore Buffett’s signature sound that became known as “trop rock,” or, as Buffett called it, “Gulf and Western,” with acoustic guitar, steel drums and pedal steel guitar injected into their backbone.

Born on Christmas Day 1946 in Pascagoula, Mississippi, Buffett grew up in nearby Mobile, Alabama, where he developed a love of sailing from his grandfather.

He started playing guitar while at Auburn University and subsequently moved to Nashville to release his first country album, “Down to Earth,” in 1970.

But it was a 1971 trip to Key West with fellow country music singer-songwriter Jerry Jeff Walker (“Mr. Bojangles”) that altered Buffett’s musical direction from outlaw country to Calypso folk-pop.

While Buffett bred a persona of lackadaisical living through his lighthearted songs that offered fans a musical escape hatch from real life, he was also asserting his business acumen.

He opened his first Margaritaville store in Key West in 1985 and followed it two years later with a nearby Margaritaville Café.

Since that initial endeavor, Buffett built an empire encompassing apparel, resorts, restaurants (including 5 O’Clock Somewhere Bar & Grill and LandShark Bar & Grill), beer (LandShark Lager), casinos, a radio station (Radio Margaritaville on SiriusXM) and retirement communities dubbed Latitude Margaritaville.

In 2017, Forbes estimated that the Margaritaville global lifestyle brand had more than $4.8 billion in the development pipeline and garnered $1.5 billion in annual sales.

As of June 2023, Forbes listed Buffett’s worth at $1 billion.

“If you’re an artist, if you want to have control of your life . . . then you gotta be a businessman, like it or not,” Buffett told Forbes in 1994. “So the businessman evolved out of being an artist.”

Buffett told USA TODAY in 2022 that being “a sponge of ideas” helped him determine his numerous business ventures.

“It’s that unexpected phone call that comes along and you say, ‘That sounds interesting.’ It’s got to be the right time, the right feeling and there has to be a lot of luck in it, too.”

But Buffett’s business building didn’t quash his creative endeavors.

In addition to his 30 albums, he launched Margaritaville Records in the early ‘90s, wrote several fiction books (including the bestsellers “Tales From Margaritaville” and “Where is Joe Merchant?”) and dabbled in film and TV via musical contributions (“Fast Times at Ridgemont High,” “Urban Cowboy”) and cameos (“Jurassic World,” “NCIS: New Orleans”).

In 2018, “Escape to Margaritaville” debuted on Broadway to mixed reviews and closed after five months; the musical continued as a touring production.

With the 2020 release of his final album,”Life on the Flipside,” Buffett spoke about the song “Live Like It’s Your Last Day,” which he said was inspired by his 1994 plane crash and a stage fall in 2011.

"I've had a couple close calls and I'm still here,” he told USA TODAY. “So I think I've been living like it could be my last day for a long time."