Everyone from Homestar Runner
Strongbad!
Strong Bad doubting his artistic skills
the embodiment of all things bad paints a serene landscape on his easel
Skull and crossbones in front of a sunset background.
A jolly roger is getting its photo taken for a job interview, with horrible photoshop job for a background.
Pirates
a nose without nostrils
I smell food
Doodle or Die is the game of "telephone" with drawing!
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