Craigslist may be the current home to creepy classifieds, but it all started with newspapers. If you could afford 5 bucks a letter (or whatever it was), you could create an ad saying anything you wanted. Often they were funny. Often they were creepy. Sometimes, they were both.
Creepy Classifieds: The Funniest Ads Newspapers Have Ever Printed (PICTURES)
Creepy Classifieds: The Funniest Ads Newspapers Have Ever Printed (PICTURES)