Ok, well maybe more weird than funny but still worth sharing:
During my college program I was a cast member at World of Disney at Downtown Disney Marketplace. The store is huge as you all know, and very very crowded, especially in the evening. I had a family at my counter and I was merchantaining them... when I got to their total, which was fairly steep, the man went to get his extra cash out. Instead of reaching for his wallet or bag or purse of some kind... he proceeded to unbuckle his belt, unzip his shorts, and reveal a lime green speedo type thong thing, and reach inside and pull out a wad of cash.
He handed me his cash (slightly soggy I still remember), and I, of course, was horrified, but I couldn't really react or laugh or anything, because I'm sure that would have been embarassing to them... so I held it together until after I had finished with them.
Let's just say that was one of the most humorous experiences I had while working at good ole' World of Disney. (There are more stories, ha)