Draw Like A Pirate Day

In honor of International Talk Like A Pirate Day, I thought I’d take you on a brief voyage to a time when sea-faring thieves and blood-thirsty brigands reigned terror upon unsuspecting sailors – to a time when I was a member of a band of pirates.

This band of ne’er do well cads were masters of their fearsome weapons. There was a bass player, a guitar man or two, a drummer, and a “xylobones” player. And there was a ferocious Captain whose gravelly, rum-soaked voice commanded the crew and any sorry souls who came to hear the cannon-thundered sound of their pirate rock ‘n roll.

Captain Bogg & Salty was a Portland-based buccaneer rock band renowned for marauding the nightclubs, pirate festivals, and a public library or two around the turn of the last century. And every so often, the bosun’s pipe would call me to join the crew.

Okay, I wasn’t actually in the band. I was a hired to bring the story of the band to life by illustrating their album sleeves.

Drawing inspiration from none other than Disney Legend Marc Davis who drew much of the concept art for the Pirates of the Caribbean attractions, I drew in pen and ink and shaded them with black water color. I tried to infuse the characters with a little bit of menace, a whole lot of humor, and that true treasure every pirate seeks, freedom.

To get a look at what I mean, check out this one I drew for their Dick Dale inspired surf rock song I’m A Pirate.

Surfing Pirate, ©2004, Freddy Martin, all rights reserved. No duplicating or reposting without permission.

I hoped to create a piece, like the picture books I remember as a kid, that viewers would want to take time to look deeply at the details and hidden jokes while listening to the song. Go ahead, look deeply. Can you spy the the pirates tube-riding companion? The not-quite empty flagon of rum? Or can you figure out the true reason this part of the ocean has such killer waves?

This piece didn’t make the cut but it remains one of my favorites to this day.

Still, the pieces from that period that still give me the most joy are the back covers. Each drawing seemed to serve as an expression of the spirit of each particular album. On the back of Bedtime Stories for Pirates, you’ll find a crows’ nest full of buccaneers singing their scurvy lungs out to nobody but the gulls. The backside of Pegleg Tango features a wooden-legged privateer swinging, nay, flying through the riggings without a care in the big blue world.

But the back cover piece that delivers the most yarrr for your buck in my opinion is the marooned pirate on the back of Emphatical Piratical. I’ll give you a look at it in just a second, but first I want to give you a step-by-step view of its creation, from concept to final piece.

First, Loren Hoskins and Kevin Hendrickson, the creative forces behind Captain Bogg & Salty came up with a concept for me – a marooned pirate who isn’t too upset about it. The music they’d been writing for the album had a laid back, island paradise feel and they thought their stranded castaway might whiling away his years on a white sandy beach.

Marooned Pirate concept sketch, ©2004 Freddy Martin, all rights reserved. No duplicating or reposting without permission.

So I plopped him in a hammock, looking out to see with a tasty coconut rum in his good hand. We loved the concept and could truly feel his relaxation coming to fruition. But with his face away from the camera, we didn’t quite have the same character driven fun we did with the other back covers. It could also look like he’s waiting for someone to come, hoping to be rescued.

Not our pirate. We wanted him to appear like he has found heaven on earth, so we turned him around.

Marooned Pirate concept sketch, ©2004 Freddy Martin, all rights reserved. No duplicating or reposting without permission.

Now we were getting somewhere. The look on this pirate’s face communicates pure joy. He doesn’t care if anybody ever finds him. You can almost smell the hibiscus. The site gag of the satisfied marauder marking an X where he’s found his treasure makes the point perfectly. This is the spot!

Before we could go further, we needed to take time to flesh out what our pirate would look like. The pirates in each of the illustrations represented a vast crew of pirates from across the seven seas, so we wanted to be careful not to repeat a face, or identify any particular character from the songs.

So I took some time and drew a line up of likely lads for the pirates in Portland to peruse and pick.

Marooned Pirate character studies, ©2004 Freddy Martin, all rights reserved. No duplicating or reposting without permission.

Now here was a rogues’ gallery of villains sure to give the mommies nightmares and the kiddies dreams of going to sea. With a little deliberation, and much talk about their possible crimes and back stories, we settled on the Spanish gentleman in the bottom right.

Huzzah! I was finally able to start work on the final piece. I played the rough cuts of the new songs over and over. Frogg Island, The Purple Tiki, The Plank Walker, and Waltz of the Waves kept me company as I drew fresh inspiration for the illustration from the lyrics.

Marooned Pirate, ©2004 Hendrickson Hoskins, LLC, all rights reserved. No duplicating or reposting without permission.

Take off your shoes and pore over this illustration on island time. See if you can find all the hidden clues about this freebooting fellow and his new life here in paradise.

Also, get ye to iTunes quick to download each and every one of Captain Bogg & Salty’s amazingly piratey albums. Privateering music fans of all ages will be able to get funky with the crew of the good ship Pollywogg. And if your younger pirates tell you they recognize the voices, you’ll be pleased to find out that these same buccaneers went on to create the songs and music for Disney Junior’s Jake and the Never Land Pirates. That’s right. Captain Bogg & Salty once set sail under the names Sharky and Bones under the notorious Captain Hook!

If you enjoyed diving into my illustrations, let me know in the comments below and I’ll make sure to open the junk drawer more often. And if you’d prefer to read more about other types of adventures, I’d like to know that too. You’re the reason I write, and I can’t thank you enough for allowing me the opportunity to share my take on the world with you.


All content, and especially the artwork, enjoy the protection afforded all intellectual property. Some of it belongs to Fred Martin and some of it belongs to Hendrickson Hoskins, LLC. Please do not use it without first gaining permission. 


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