i've used heaps of different vending machines in japan. some of the more noteable ones are:
hanukin toy park in ginza has toy vending machines out the front so you can buy toys after closing time. They even come with wrapping and a Hanukin toy Park shopping bag (very important if you are buying a gift).
in a hotel I once stayed at in Shinjuku (well
Kabuki-cho actually) there was one that sold underwear (mens, and new, not used) and toothbrushes and also whiskey! the one next to it sold hot food, like potato fries, takoyaki etc.
one in chiba in the middle of no where (chiba-minato, in a back street) I was walking past and noticed it sold beer. but even had the big 1litre and 2 litre cans! the 2litre cans were quite expensive around 2,000 or 3,000 yen I think, so I had to use a 10,000 yen note and the bastard machine ripped me off, took my 10,000yen and didn't give me any beer! My friend lost hist temper and smacked the machine and it broke his watch. haha, robbed and beaten up by a japanese vending machine.
There is another very old school looking vending machine in kabuki-cho that dispenses racy lingerie.
My favourites are in winter when I buy my boss coffee (love WEB, rainbow mountain is good too) and at night (well usually like 3 or 4 am) on the way home I buy a semi-sweet cocoa (dont care which brand they are all pretty similar, kirin, asahi, CCA etc). Also when it's really cold and I'm starving I love a can of the corn soup. so I get a can of corn soup to warm one pocket, and some coffee for the other. nice.
and I've never seen a used pantie vending machine and believe me I've been keeping an eye out for this one. harder to find than the loch ness monster I think. and if there ever was any, they are probably long gone now.