About to hit 17 years in the industry now so seen a few..
Sold a scanner to a strip club, I was new to the industry and just a teenager at the time - made the mistake of asking what they wanted to scan
Had a "serviced" copier in a massage parlour (inherited the install base so I cant take credit for this)
Sold/installed copiers/MFD's to both of the last two Prime Ministers offices/houses
Installed a fax machine INSIDE a jail, there was a very dusty gap and some cables on the desk so I asked what happened to the last one... it was stolen
Installed a printer to print orders for an online Viagra business
Sold the colour printer used to generate the slides to pitch for the original Lord of The Rings Movie
That's all I can think of right now...