Right, as this seems to have died a death, I'm going to use our new found currency to dish out some prizes for the best guesses. My current stash of money stands at $14880 (after this post), which neatly divides into 5 prizes of $2970. ($2976 rounded down, and leaving me with $30).
So my 5 favourite guesses (in no particular order):
1 GBM's guess of 'Spam', for not only starting the topic but also knowing what makes me tick...
2 Fedele's guess of 'A pervertable', because everyone loves pervertables.
3 IG's guess of 'Extra toner for his fax macheene', for reminding me of a silly afternoon in the OOC.
4 Flem's guess of a Russian doll head and hat combo effect, for being especially silly and deep at the same time.
and,
5 VB's guess of 'The Human League', for providing a perfect finisher to the mental image I now have of my hat with these 5 things in.
So all of you, well done, I'll be PMing Hers to sort out your winnings. As for everyone else, don't feel too down as it was very difficult sorting them out, and once I've dragged myself up from destitution, I might do another round of this...