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You know Robin Hood right? I was about to made some kind of parody dressing him up in red, with a sickle and a hammer on the hat and with a money bag. It was "Robin Hood: the 12th century communist"
Because of the stealing the rich and giving money to the poor people stuff, you know.
Anyway, since I had the idea I've done like 10 sketches and all I got was a complete and absolute shit. Most of the time I notice I'm just drawing the same position but with slight changes. And I quit after 30 mins trying and getting nothing.
What do you do when you've got a good idea but you can't develop it?
Let go of your self imposed restrictions... for instance, "dressing him up in red, with a sickle and a hammer on the hat and with a money bag."
Just draw STUFF for a while, shapes, play with colour combos and schemes, thumbnails with less focus on the specifics. Then you're more likely to come up with a design that incorporates things besides the obvious.
Plus it's a ton of fun.
Is he just standing there or actually doing something? What type of situation is he in? If he has a purpose, you might find a way of drawing him.
Sinse you allready know all the props he has on, forget them. Start with a silhuette, just to find a strong pose...then add all the other stuff. A good ol' propaganda poster perspective of him standing jumps to mind (but that's the pose you've probably fucked up over and over heh). Try something along the lines of him sneaking into some underground millionaire's basement, cause being a millionaire is against communism and his about to redistribute some wealth..