Usually I just focus on making my art funny and place little effort on actually creating an aesthetically pleasing picture. In the case of 'Somali Pirates,' I was inspired by the well-drawn, maritime-themed artworks of hellopirate2 and I wanted to spend a little more time creating something that looked nice.
And behold! Somali pirates are fearsome and dangerous in real life, but in MS Paint they're just lovable little rapscallions. In addition to the menacing assault rifle and rocket launcher, I added some unrealistic/anachronistic features such as a parrot and sheathed sword.
Add a smile to one of the pirates, and suddenly they seem completely disarmed.
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