My personal favorite is the old Pregnant Nun- not sure what to recommend for your friend however along the same theme (also may be offensive to some)

A bald man with a wooden leg was invited to a halloween party and went to the local costume shop to get his costume. The attendant said, "I know exactly what you need!" and returned shortly with a pirates costume. He told the gentleman, "With your wooden leg, this would be perfect". The man blew up, "How can you even suggest such a thing- I am very self conscious about my wooden leg- take that back and get me something else at once!"

The attendant came back shortly with a monk's costume- he told the man, "The long robe will cover up your wooden leg and this will really take advantage of your shiny pate". The man was really incensed now- he told the attendant what he could do with the monk's costume and told him to get him a different costume.

A while later, the attendant came back with a can of red spray paint and a bag of caramels. He told the man, "Paint yourself red, while you are drying, melt the caramels in a pan. Pour the caramels over your little bald head, stick your wooden leg up your *ss and go as a Caramel Apple!"

DISCLAIMER- this post is not designed to offend catholics, pirates, monks, people who are tress challenged or those with wooden legs- no flames please! Laura