Pickle Incident, The

Originating in a Fark.com photoshop contest back in December 2002. The contest began as normal, with the usual clever but innocuous submissions. Until one unfortunate soul attempted to submit a picture of an amended Star Trek magazine cover, with the caption "where no man has gone before". Sadly, the picture that was actually submitted was a graphic close-up of a man with a very large pickle (or more likely, a cucumber) inserted into his ass.

The caption remained.