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If someone else brought me a show concept that they wanted to be "hip", I would go as stylized and flat as possible, because I knew nothing else about the show would have any interest. No story, humor or personality.
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If I wanted to come up with a specific gag, the drawing couldn't be restricted by strict geometric rules so I found a middle ground between constructed characters and some stylization - angles in sensible places that wouldn't distract from the overall image or gag - character. These things are supposed to be alive, drawn comedians.
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There's lots more of this kind of stuff. Maybe I'll put some more up later so you can make fun of it, since I made fun of its modern descendants.
i think a lot of young cartoonists go through their "I wanna be hip" period. I had one, but I kept getting distracted by my natural instincts to want to be funny and entertaining and pure flatness wouldn't allow it.
What I'm amazed by today is that the super flat stuff has lasted almost 20 years - way beyond a normal allowance for what should be a passing trend. And that makes it no longer the least bit rebellious because everyone and his dog does it. It's become so simple that now anybody could draw it. It's now the purist form of conservatism.
Pete Emslie, Design-Master at Sheridan college weighs in. He says it better than me.
http://cartooncave.blogspot.com/2009/09/limitations-of-contemporary-tv.html