My grandfather's name was Colon. Not Colin, Colon. Spelled and pronounced like a certain part of the human digestive system. When he died I went to the website of my local newspaper to read his obituary and found the page adorned with ads for "Colon Health" and "Colon Cleansing". That was my first introduction to contextual advertising.
In newspaper parlance its called "tombstoning"; when two unrelated items on a page combine in the mind of the observer in an absurd or humorous way. This association is created between two items by their proximity to each other or their relative positions in a page's layout.
In the online world these random associations happen constantly. Whether its contextual advertising, which scans the text of a page and serves up relevant but sometimes wholly inappropriate ads, or content management systems, which treats content like interchangeable blocks. It might even be an online retailer that produces some wacky recommendations when someone buys both children's and adult-type toys. When webpages are dynamically generated, database driven and templated these unfortunate juxtapositions are inevitable and the less a human editor is required to shepherd the process of online publishing the more absurd they are likely to get.
Through the years I've collected these gems whenever I came across them. On this site I'll share my collection with you and ask you to submit your own.