Pirates Archives | Freelance cartoonist and illustrator

Pirate Folk Song; The Ballad of Shillelagh O’Toole

Never was any pirate so cruel, than the old Irish pirate, Shillelagh O’Toole!

This was a little commission piece, created to illustrate the front cover of a pirate folk song, written by the very talented Robert Palomo.

And being he was an Irish pirate, I’ve used some shades of emerald green on all of his clothing, but this also aids in making him stand out against a primarily brown backdrop – perfect for small phone and iPod screens!

In his hand is his weapon of choice, the dreaded blackthorn shillelagh, and top his shoulder rides a rather squawky (and probably unstable) parrot! If you look carefully, there’s also a little crab hiding out in his pocket.

To complete the scene, we’ve a circle of rather trembly arms that belong to an extremely scared ship crew, each brandishing a weapon!

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Walk The Plank Cartoon

What’s the best thing to do with a mutinous sea dog? Make him walk the plank of course!

Here is another of my cartoon pirate characters in a little bit of a situation… It would seem his shipmates feel he should be made to walk the plank!

Created firstly as a pencil sketch, this cartoon pirate was then scanned in and the outlines digitised.

The next stage was to add in all of the base colours, followed by a little shading and required highlights.

I’ve also added in a little flex in the plank to suggest some weight in the pirate character.

He is also the perfect accompaniment to the other cartoon pirates that can be found roaming in my portfolio!

Cartoon King

Bow down all before the might of the cartoon king!

This cartoon king is another of my cartoon illustrations created for ‘The Pirate Deck’ card game.

Wearing a regal red cloak and brandishing a mighty sword, he’s the perfect character to keep those unruly pirates in line!

Created firstly as a pencil sketch, he was then scanned in and all of the outlines digitised.

The next stage was adding all of the base colours, such as the skin and clothing and then finally the details and shading, such as the metallic sheen on parts of his armour.

This particular cartoon king is based upon William of Orange (or King William III), who was ruler of England during the 1600’s (and affectionately known in this household as ‘Billy Tango’).

Pirate Cannon Cartoon

Avast Ye! This be a pirate cannon cartoon and he be aiming right at you! This crazy looking little chap is another of my pirate creations to feature in an up and coming card game.

The pirate cannon was created firstly in pencils, before scanning in and adding some digital outlines. The next step was to then add in the base colours and finally a little shading to bring the pirate cannon to life.

I also like the cracked skull sitting at the front of the cannon – not sure whether this is an enemy or a relative, but his teeth appear to be in good condition!

When creating the pirate cannon cartoon, I also took some time to create a desert island themed backdrop, complete with palm tree.

Pirate Ghost Cartoon

Who you gonna call? Well, ideally someone who knows how to deal with a pirate ghost!

Draped in tattered and torn clothing and sporting a rather fetching hat, he now spends an eternity as a ghost due to an unfortunate encounter with a cannon!

This rather spooky character is another commission piece as part of The Pirate Deck card game.

The pirate ghost was created firstly as a quick pencil sketch. He was then scanned in and all outlines were then digitised.

The next step was to apply all the spooky green base colours, before adding in some highlights and shading where required.

Zombie Pirate Cartoon

Here we have a rather squelchy zombie pirate cartoon, dressed in weathered pirate attire and complete with a rather hungry fish chomping on his finger!

The zombie pirate cartoon was created firstly as a pencil sketch and then digitised using Adobe Illustrator before adding in final colours and detail, such as the tentacle in his pocket!

The zombie pirate will feature as one of the action cards in the up and coming Pirate Deck card game, which is currently in development – the perfect accompaniment to my other cartoon zombie!

Cartoon Shark

Imagine dipping a toe into the water, only to be confronted by the cartoon shark – complete with a menacing grin and lots of pointy teeth!

Created initially as a pencil sketch and then digital outlines were applied, before adding in the base colours and then finally the shades / highlights to bring out the detail.

With the cartoon shark, I really wanted to convey an air of menace, but also a slightly friendly edge, which I think works well. I think I’d hummed the ‘Jaws’ theme on more than one occasion too!

He’s looking pretty hungry – I’d imagine the cartoon dolphins in my portfolio would want to keep out of his way!

Cartoon Pirates

Avast ye! Here be a collection of cartoon pirates ready for battle off the port bow!

These cartoon pirates are all characters that have been created for the up and coming Pirate Deck card game.

First up is a fierce red-bearded cartoon pirate, complete with his cutlass, evil grimace and red-striped breaches.

We’ve also a peg-leg pirate captain, blurting out some orders to whoever might be listening (I’m sure it’s not his rather worried-looking parrot!).

A pirate with a grappling hook also joins the line-up. I created a custom brush for the rope in Adobe Illustrator, which allowed me to create an editable and posable rope, which I was then able to use for other pirates later in the project.

Two of the most motley of the crew are ‘Skinny Sam’ and ‘Portly Pete’ who both vary greatly in stature, but this is a key element in the Pirate Deck Card Game – one can push other cards out of the way and the other can slink in between!

As with all of my cartoon artworks, these all started out life as pencil sketches, which were then scanned in and digitised using Adobe Illustrator.