Jimmy Buffett Wrote One of His “Big 8” Songs About a “Pirate” Bartender and Foretold His Tragic End

When Jimmy Buffett first moved to Key West in the early ’70s, he started hanging out at bars and venues frequented by locals, including the Chart Room at the Pier House Motel. That is where Buffett had his first performance in Key West and also connected with Phil Clark.

Considered a modern-day pirate, Clark, who had lived in Key West since the 1960s, led the life of an outlaw. Clark had a storied life, from being a mercenary soldier and even working as an advertising executive in New York City. He was busted for smuggling marijuana from Jamaica, hung around with gun and drug runners and gamblers, and also spent time on the Virgin Islands and shared many stories with Buffett of the characters he met along the way.

Fascinated with Clark’s renegade life as a modern-day pirate, Buffett wrote what would become one of his classic “Big 8” songs—those most popular with Parrot Heads, which he performed throughout his career.

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[RELATED: Glenn Frey and Jimmy Buffett Memorialized Their Wild Parties in Aspen on the Only Song They Ever Wrote Together]

“A Pirate Looks at Forty”

Released on Buffett’s fifth album, A14 in 1974, “A Pirate Looks at Forty” was his ode to Clark’s adventurous life.

Mother, mother ocean, I have heard you call
Wanted to sail upon your waters since I was three feet tall
You’ve seen it all, you’ve seen it all

Watched the men who rode you switch from sails to steam
And in your belly, you hold the treasures few have ever seen
Most of ’em dream, most of ’em dream

Yes, I am a pirate, two hundred years too late
The cannons don’t thunder, there’s nothing to plunder
I’m an over-forty victim of fate
Arriving too late, arriving too late

Wanted to sail upon your waters since I was three feet tall
You’ve seen it all, you’ve seen it all

Watched the men who rode you switch from sails to steam
And in your belly, you hold the treasures few have ever seen
Most of ’em dream, most of ’em dream

Eventually, Clark’s luck ran out when he was busted carrying “10 tons of cargo” and went to jail in Orlando. “When he bonded out and came back to Key West, his vitality seemed quenched,” said Carol Shaughnessy, who was engaged to Clark and later became the first editor for Jimmy Buffett’s Coconut Telegraph newsletter and handled his fan correspondences, and worked as his publicist.

“He [Clark] had made private plans to say his farewells and disappear,” Shaughnessy added. “The last time I saw him, it flashed through my mind that … someone would come to tell me he was dead.”

Later living under an alias, Clark worked as a bartender in Sausalito under an assumed name and died by drowning in the San Francisco Bay in the mid-’80s. His death was somehow foreshadowed in Buffett’s “A Pirate Looks at Forty” lyrics.

Mother, mother ocean, after all the years I’ve found
My occupational hazard being my occupation’s just not around
I feel like I’ve drowned, gonna head uptown
I feel like I’ve drowned, gonna head uptown

Covers

Buffett later called his 2000 autobiography, A Pirate Looks at Fifty, and the song lived on with some covers throughout the decades.

During the Peace Sunday rally in Pasadena, California, in 1982, Bob Dylan and Joan Baez performed “A Pirate Looks at Forty.” Jack Johnson has also covered “A Pirate Looks at Forty” live for years and released his version on the 2002 soundtrack to The September Sessions.

The day of Buffett’s death in September 2023 at age 76, Dave Matthews also performed the classic in his honor.

Photo: Michael Ochs Archives/Getty Images