Can robots have a sense of humour? And would we find it funny?

In Catch 22 wounded officers in hospital are given enlisted men’s letters to redact of any sensitive military detail. Some of the letters are to girl friends back home and are very sexually graphic but most are from sons to mothers and are very dull. The officers quickly become board with the task and devise ways of making it more interesting. Like redacting every forth word, or every word with a certain letter in it, or taking out all the words except the swear words. But even this gets a bit boring after a while so the main character redacts every thing but the , “dear mum”and the “your loving son”. So what would happen if an AI  was given the task? Would they complete it without deviation endlessly or would their superior intelligence eventually mean they would be capable of subtlety subverting the task? 

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