On The Simpsons, however, the characters are nothing but stereotype. They’re practically Pyncheonesque in their emptiness — not people, but objects who get driven through various pastiches in order to become the butt of the audience’s arch, ironic jokes. I didn’t give a shit about any of them. The only way I could enjoy these characters was to say, “Haha look at the funny dumb poor people who are so incredibly stupid that they actually work at nuclear power plants.”I don't know what's worse: the failure to understand The Simpsons, the failure to understand Pynchon, or the over-the-top knee-jerk reaction against strawman hipsters (with their "arch, ironic" jokes).
There seems to be an assumption that there is an intellectual elite sitting somewhere in their towers mocking dumb poor people for sport and profit. When in fact, that is exactly the sort of situation that would be ably lampooned on The Simpsons (with a guest appearance from Wes Anderson and a Royal Tenenbaums spoof). Because it is the situations in The Simpsons that we are meant to laugh at and the way they expose unspoken desires and power relations in the real world (just like a Pynchon novel).
If Homer seems like a stereotype its because he is archetypal in the same way Bugs Bunny is: able to be dropped into any storyline, role, or pastiche while maintaining his core identity. More importantly we don't laugh at Homer so much as recognize that his dumbness is a reflection of the world he lives in. We sympathize with Homer for his laziness, inflated sense of importance, weakness for donuts, and talent for disappointment (d'oh!). He is us. He is our everyman. At the same time he is also all of our own worst habits, all those things that annoy us in everybody else
Perhaps good comedies exploit that same tension that we find in the fear and entertainment experienced by audiences in a horror movie: "the frisson of ambivalent feelings". In The Simpsons we have characters who remind us that life is both wonderful and stupid. We laugh with as we laugh at and that ambivalence is what makes the show so brilliant.
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As for Pynchon, his latest book, Against the Day, is a steam-punk epic and a meditation on the unnecessary violence that gave birth to the modern world. His characters begin as types, but their true humanity is revealed for those patient enough to read to the end. No joke.