Here are some video sketches which are somehow related to IT.
Lets start with bad humor. I don't like this kind of attitude to customers: yes, they often don't know what they want; yes, they often don't know how to properly name things - but the mission of IT guy in this situation is to understand what is actually needed, not to prove, that customer is stupid and doesn't understand the topic.
This sketch shows how unprofessional IT "expert" actually is, not how stupid requirements customers order.
This one is better. Not very funny but at least accurate and not offensive:
And these are really good: 2 parts of If Google Was a Guy: