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The Meaning of Jimmy Buffett’s “A Pirate Looks at Forty”

A1A by Jimmy Buffett (1974).

Jimmy Buffett is known for writing ocean-minded music that goes hand in hand with boats, beaches, and of course, booze. “A Pirate Looks at Forty” is a classic example of this, and one that hits close to home for many a mariner, as they enter “mid adulthood”.

Released in 1974 on Jimmy Buffett’s classic fifth album, A1A, which also contains another fan-favorite, “Tin Cup Chalice”, “A Pirate Looks at Forty” represents the songwriter at his very best. The song presents an old swashbuckler who has been around for a while, and has done some questionable things in pursuit of the booty.

Now, aging into his forties, this pirate looks back on his life and sees that not only was he born in the wrong decade, he’s already made plenty of mistakes and he intends to make some more.

The latter is a common thread in Buffett’s music and part of what makes it so relatable, as it brings an element of humanity to the feel-good island lifestyle that he sings about.

“A Pirate Looks at Forty” Origins

According to the now-defunct fan site called the Church of Buffett Orthodox, “A Pirate Looks at Forty” was inspired by a real life person whom was living in Key West when Buffett first arrived there as an undiscovered singer-songwriter in 1970.

This man was Phillips “Phil” Clark, a local legend who tended bar at The Chart Room Bar at the Pier House Hotel. The Church of Buffett included a note from a fellow bartender, whom worked alongside Clark, which we have accessed via the Internet Archive’s Wayback Machine:

Phil and Vic Latham and I were the bartenders at The Chart Room Bar at the Pier House in 70 and 71 and 72. Our friend Jerry Jeff Walker was living in Coconut Grove with a young woman named Murphy Fernandez, and JJ and Murphy brought this out-of-work picker from Alabama to Key West for R&R; in November 71. The first place they brought Jimmy was The Chart Room, and I was the bartender on duty.

I handed JB a cold beer and told him, “The first one’s free.” I think that’s when he knew that Key West was the place for him. Anyway, we looked at Phil as some kind of wild Caribbean adventurer because he’d spent a lot of time in the Virgin Islands with characters of dubious repute, and Phil had already been busted for trying to fly some pot in from Jamaica. He had been a bartender in New York, claimed to have dated Lauren Huttton before she was famous, lived with the Mamas and Papas on the beach in St. Thomas, hung out with gun runners and professional gamblers.

Phil had plenty of tales to tell, and occasionally one of his old cohorts would breeze through Key West, and would fit the mold of modern-day pirate. Years later, Phil married Murphy Fernandez (she was one of six wives, as I recall, and the wives, eventually, all knew each other!) Sadly, Phil drowned in San Francisco Bay in the mid-1980s. He was hiding from various elements of the law and the bonding profession, bartending in Sausalito under an assumed name. 

Chart Room Bartender recalls the legendary Phil Clark.

The above note provides some very interesting context about this Phil Clark character. Buffett confirmed Clark as the inspiration behind the song in 1991, prior to performing the track alongside fellow Key West hang-around Jerry Jeff Walker.

Watch that video below, and read on for a full lyrical analysis.

“A Pirate Looks at Forty” Lyrics Meaning

Lyrically, “A Pirate Looks at Forty” is from the perspective of this old mariner, aging out of his glory days and struggling to come to grips with the modern world. Still, he maintains a love and respect for the ocean, something that is essential for a life on the water.

This begins with the first verse:

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

First verse to “A Pirate Looks at Forty” by Jimmy Buffett.

This mariner recalls hearing the call of the ocean from when they were just a young boy, in awe of its all-knowing and eternal nature.

The second verse reveals his stance as an old-timer, while still maintaining that respect for mother ocean:

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

Second verse to “A Pirate Looks at Forty” by Jimmy Buffett.

Here, he says that the ocean has seen its men switch from vessels powered by sails to vessels powered by engines. There are things at the bottom, sunken treasure and other mysteries, that most mariners can only dream of, thus increasing the allure of the ocean.

Next, our narrator shares his plight:

Yes I am a pirate, two hundred years too late
The cannons don’t thunder, there’s nothin’ to plunder
I’m an over-forty victim of fate
Arriving too late, arriving too late

Third verse to “A Pirate Looks at Forty” by Jimmy Buffett.

Born in the modern era, this pirate missed his chance to fire cannons and plunder the booty. Now, he’s over forty, losing his youthful ambition, and grappling with the frustration of being adrift.

In the fourth verse, however, we see that he certainly has partaken in his share of piracy:

I’ve done a bit of smugglin’, I’ve run my share of grass
I made enough money to buy Miami, but I pissed it away so fast
Never meant to last, never meant to last

Fourth verse to “A Pirate Looks at Forty” by Jimmy Buffett.

When he refers to “running grass”, he means taking cannabis by boat from Cuba or elsewhere and bringing it into the United States for sale. Specifically, to Miami, which he says that he could have bought in his prime.

However, he wasted all his money and now he has nothing to show for it. He consoles himself with the notion that it was never meant to last, anyway.

The fifth verse shows that he’s at a low point in life:

And I have been drunk now for over two weeks
I passed out and I rallied and I sprung a few leaks
But I got to stop wishin’, got to go fishin’
Down to rock bottom again
Just a few friends, just a few friends

Fifth verse to “A Pirate Looks at Forty” by Jimmy Buffett.

He’s been on a bender, drinking for two weeks. Passing out, waking up and starting again. He’s had some issues along the way, but he’s still standing.

There’s a double meaning inherent here, when he says he sprung a few leaks. He could be talking about his boat, or metaphorically about his life. Same goes for the next line about fishing.

Then, he mentions being ready for rock bottom. And it isn’t the first time, but he’s got some friends down there to hang around with.

His issues are further highlighted in the sixth verse:

I go for younger women, lived with several awhile
Though I ran ’em away, they’d come back one day
Still could manage to smile
Just takes a while, just takes a while

Sixth verse to “A Pirate Looks at Forty” by Jimmy Buffett.

Apparently, this sailor is not only struggling with his life choices, he also has some emotional demons to face. He has run off every woman in his life, but somehow still thinks they’ll come back around.

Sometimes, he can smile. It’s just not so easy these days. Maybe it requires a few drinks.

Finally, the closing lyrics further emphasize that this is a cyclical pattern for our narrator:

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

Outro to “A Pirate Looks at Forty” by Jimmy Buffett.

His biggest danger with work is that his chosen profession — piracy — no longer exists. He’s overwhelmed with this knowledge, and feels like he’s drowning. His solution? Head out for a few drinks, at rock bottom with his friends.

Listen to “A Pirate Looks at Forty” below.

Jimmy Buffet – “A Pirate Looks at Forty”

Jack Johnson & Dave Matthews Version

At the 2008 Kokua Festival in Hawaii, Jack Johnson was joined by Dave Matthews and Tim Reynolds for a wonderful rendition of “A Pirate Looks at Forty”. This version has a great vibe, and was even recorded on video. The video below also includes a song about recycling, after the Buffett cover.

Jack Johnson, Dave Matthews, and Tim Reynolds – “A Pirate Looks at Forty”