Dilbert's success can be traced to its all-too-accurate portrayal of corporate culture as a Kafkaesque world of bureaucracy for its own sake.
The boss has power, but no skill; the workers have skills, but no power – and as they learn that their skills are not rewarded, they become mere placeholders who see innovation as dangerous and count anonymity as success.
The humor emerges as we see the characters making obviously ridiculous decisions, and we realize that the artificial roles assigned to each member of the corporate culture often require us to do exactly the same thing.
/Cow-orker?
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