A Pirate Looks at Forty singing a Pirate Song with Pirates & Parrots in a Sea Shanty Medley!

Hello, my favorite Monday peeps! I hope everyone had a fabulous weekend! Ours was actually pretty mellow for the most part—which was especially welcome after Mother Nature decided to kick things off Friday with a wild and crazy storm that knocked out our power. 😳⛈️

Let’s just say she certainly knows how to make an entrance! But I’ll save those shenanigans for tomorrow. 😉 Thankfully, the rest of the weekend was much calmer, and as usual, it zipped by entirely too fast. How is it Monday again already?!

This week is a theme week for Monday’s Music Moves Me, and we’re heading out onto the high seas! Cathy gave us this fun assignment: “Recently, it was International Talk Like a Pirate Day, a fun modern holiday. It would be fun to see where the seven seas take each of you as you share with us songs relating to pirates.”

Arrrrr you ready? 😂 Because I had entirely too much fun with this one! We’re starting with a legendary island-loving troubadour and a pirate contemplating the passage of time, then setting sail with another country superstar who dreams of trading everyday life for a pirate’s freedom.

From there, we’ll raise a glass to the ultimate modern-day pirate with a song celebrating the incredible musical legacy he left behind, before gathering the whole crew for a rowdy a cappella voyage across the seven seas. So grab your eye patch, hoist the Jolly Roger, and let’s see where the musical tides take us!

We couldn’t possibly set sail on a pirate-themed Monday without inviting the man who practically made the island-and-ocean lifestyle its own musical genre! This 1974 classic wasn’t simply dreamed up as a fictional pirate tale, either.

It was inspired by a real Key West character named Phil Clark, whom the singer knew from his early days hanging around the Chart Room. Clark was a sailor and smuggler whose colorful life provided the perfect inspiration for a modern-day pirate who feels as though he was born a couple of centuries too late.

But beneath all that pirate imagery is actually a surprisingly reflective song about getting older and taking stock of where life has carried you. Our modern-day pirate looks back at the adventures, mistakes and questionable choices of his first four decades while wondering what might still be waiting beyond the horizon.

It became one of the singer’s most beloved songs—one he performed at nearly every concert—and there’s something wonderfully appropriate about beginning our voyage with a pirate who isn’t searching for buried treasure so much as looking back at the life he’s already lived.

Get ready to dance; here’s the late great Jimmy Buffett with “A Pirate Looks at Forty”:

From a pirate who believes he was born in the wrong century, we’re moving on to someone who’s perfectly happy to fantasize about trading modern life for one spent sailing the Caribbean.

This dreamy little escape appeared on a 2018 album inspired by the people and islands of the Caribbean after Hurricane Irma caused enormous devastation there in 2017. The singer had a home on St. John and deep connections to the community, so watching friends lose homes and livelihoods hit especially close to home.

The entire album became a love letter to the islands and, more importantly, to the resilience of the people rebuilding them. He said he wanted the music to capture their ability to rise above complete chaos and begin again. Our particular selection is one of the record’s more wistful moments, imagining the freedom of leaving life’s complications behind for an existence dictated by the wind, waves and horizon.

And considering how much this singer has credited a certain legendary island-loving songwriter with introducing him to boats and life on the water, there’s a nice little invisible thread connecting our first pirate to our second.

Give a listen to Kenny Chesney with “Pirate Song”:

And speaking of that legendary island-loving songwriter, he’s still very much with us for our third selection—even though this song was written after we lost him. ❤️ Two musicians who were especially close to him turned their grief into a celebration of the friend who had meant so much to both of them.

One had collaborated with him several times over the years, while the other spent decades as a member of his band and considered him something of a big brother and mentor.

The idea grew out of a heartfelt conversation between the two shortly after their friend died. Rather than writing a somber goodbye, they imagined him somewhere with blue water, white sand and the eternal island party still going strong.

It became a bittersweet but joyful tribute to the man, his music, and the enormous family of fans he created along the way.

The song was later premiered at the Hollywood Bowl during an all-star tribute concert celebrating his life—which feels exactly right. After all, one of his final requests to his longtime bandmate was essentially to keep the party going…and that’s precisely what they’re doing.

Get ready for some major goosebumps; here’s Zac Brown Band featuring Mac McAnally with “Pirates & Parrots”:

All right, mateys—we’ve contemplated life with an aging pirate, dreamed about escaping to the islands, and raised a musical glass to a beloved Parrothead captain. There’s only one sensible thing left to do: gather the crew and start singing sea shanties! 😂 

This all-vocal group jumped aboard the sea-shanty craze in 2021 and mashed several maritime favorites together, beginning with the song that had suddenly taken over social media before sailing through a whole collection of tunes traditionally associated with sailors and life at sea.

And boy, did people respond—the group says their medley eventually racked up an astonishing 4.4 billion views across social platforms. Apparently that was enough to awaken their inner sailors permanently, because what started as one viral medley eventually inspired them to dive much deeper into maritime music, including an entire album devoted to songs of the sea.

With five guys supplying every harmony, bass note, rhythm, and sound using nothing but their voices, it’s rowdy, ridiculously fun, and practically impossible not to sing along with.

So grab your imaginary tankard, find your best pirate voice, and prepare to finish today’s voyage like a proper crew. Yo ho ho! 😂

I dare you not to dance and sing along; here’s Home Free with “Sea Shanty Medley”:

That’s a wrap for this week, me hearties – have a great Monday! May yer seas be calm, yer rum be plentiful, and I’ll see you on the dance floor! 🏴‍☠️😆

Now, onto the particulars of Monday’s Music Moves Me:

I have the supreme honor and privilege of being a co-host with the inimitable Xmas Dolly and our musical cohort, the awesome Cathy from Curious as a CAThy, and Alana of Ramblin’ with AM!

Want to join in the fun? It’s easy – just find a tune that rocks your boat, post it, and link up! Check out the other music lovahs and let’s jam!