Pynchon doesn't pretend to be anything. His material mostly consists of low culture, obscenity, and engineering nerd stuff he finds interesting. He lived through the beat and hippie countercultures and draws from them for his characters and settings.
I think people get hung up on the difficulty of his writing. He writes word puzzles and he's having as much fun with it as he can.
People like his work because they have fun untangling the obscure mess he puts on the page.