u/Adventurous-Nose-183

First time trying to draw in this art style, but last night I had the idea of The Flying Dutchman, Jolly Roger and The Kraken as bosses in the style of Cuphead, so I sat down and decided to try and sketch them out the best I could.

Jolly Roger, The Accursed Pirate

The Kraken, Collector from The Deep

The Flying Dutchman, not happy how it turned out other than the mouth and skeleton at the front

Not that happy with how the dutchman came out but it's the best I could do while using the ship from the Captain BrineyBeard boss fight in the game.

After rearranging my room a touch and cleaning? Finally got enough space to add a better "showcase" of a small portion of some Pirates of The Caribbean merch and some other random nautical stuff I have around my room.

https://preview.redd.it/0x0e4q5gqq1h1.png?width=1279&format=png&auto=webp&s=95836f33474953c990c0e8d575e2a16f93fcb478

The reason why the dutchman doesn't have all of it's sails by the way, is due to them being able to fall of easier so I put them with the rest of the spare parts I have into storage.

E3 2006 special print of Jolly Roger from Pirates of The Caribbean Online

Mega Bloks Kraken, 3D printed Potc Kraken model and the beta pass disc which was given out at E3 2006, along with a close up of the Mega Bloks Dutchman

Davy Jones, Clanker and Maccus Mega Bloks figurines

AWE Human Jones figure, a wall decoration of a Octopus and a Corgi embroidery my sister made one year for Christmas, not pirate themed but there is one of a corgi on a squid behind it.

a near 1:1 sized Dead Man's Chest, 2 Kraken Spiced Rum Bottles (One from orlando florida), a vintage navy sailor figure I got and a painting my sister did of a Kraken

The stuff on the left in the first image is a skeletal mermaid, a ship that I've had since I was like 12 that was used for aquariums and a starfish from an old "sea life" type collection from Hilton Head, which I got for one of my birthdays, can't get a clear image of them sadly due to the glare and sunlight.

In highlight of some awesome recent news...

Here's my own take on designing the kraken based off of some illustrations, mainly the one done by Hodari ShadowWalker on Twitter!

https://preview.redd.it/lcv5vbfswexg1.png?width=1404&format=png&auto=webp&s=4efc164580b9fa909c212451c5ddc3c2ad6a222d