The tradition of writing a funny best man speech for modern weddings is fairly new. The wedding tradition of a best man speaking has evolved from respectful well wishing to pithy toasting of the happy couple and in particular the groom. The risk of taking well meaning jabs and over-reaching to tasteless mockery is the tricky fine line that all too often gets crossed.
The goal of a funny best man speech should be to humanize the groom. The best man should highlight that which is best in the groom’s character, without berating or demolishing the groom’s image. In other words, the best man should share the embarrassment with the groom, not place himself in a more positive light.
One approach is for the best man to assume a mutually self-deprecating role along side the groom. A story of a time when tom-foolery lead to a sticky situation when the best man and groom found themselves in an embarrassing or hostile situation, only to emerge through the ordeal by virtue of their loyalty and camaraderie is a good foundation.
Another approach is for the best man to take the burden of self-deprecation wholly on himself. A classic comedy set up is to have a two-man team where one plays the straight-man and the other plays the fool, such as an Abbot and Costello routine. The best man would then bring out what’s best in the groom’s character by describing the groom’s virtues complementing the best mans vices.