Today’s classic song of the day is Jimmy Buffett’s “A Pirate Looks at Forty.” Released as a single in February of 1975, this one didn’t quite crack the Billboard Hot 100, stalling out at #101. (Missed it by that much…)
“A Pirate Looks at Forty” is about a washed-up drug smuggler turning the big 4-0, looking back on his life and lamenting that he’d have rather been a pirate. Jimmy Buffett wrote the song about Phil Clark, a character he met at the Chart Room Bar when he first moved to Key West. Mr. Clark had lived a number of lives by then, including advertising executive, bartender, gambler, gunrunner, and, yes, gentleman drug smuggler.
Here’s Mr. Buffett’s recollection:
“The real pirate’s name was Phillip Clark. He was one of the most unforgettable characters I met when I first lived in Key West, back in the days before it turned into a boutique. When I finished the song, I knew I had done him justice, and it is a fitting eulogy to an old friend. He died a few years ago under an alias, washed up on a beach near San Francisco. They flew his body back to Key West where some of his ashes were scattered at sea, and some still sit above the cash register in the Full Moon Saloon.”

It’s all there in the lyrics:
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
I’ve done a bit of smugglin’, and 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
Interestingly, “A Pirate Looks at Forty” was produced by a gent named Don Gant. Mr. Gant was the vocalist in the group Neon Philharmonic, which was the psychedelic brain child of one Tupper Saussy. You can read more about Mr. Saussy and the Neon Philharmonic in my write up of their big hit, “Morning Girl.” It’s an interesting read.
As Mr. Buffett said, Phil Clark drowned in San Francisco Bay sometime in the mid-80s. Jimmy Buffett passed away in 2023, 76 years old.
For your viewing and listening pleasure, here’s today’s daily bonus video of the day. It’s Jimmy Buffett and the Zach Brown Band performing “A Pirate Looks at Forty” back in 2010 on the CMT Crossroads program.