I’ve spent a certain amount of time looking at contextual advertising systems. During my time at Overture Research, I helped build a system to evaluate them. Needless to say, I’ve seen my share of bad ad placement.
My personal all time favorite was on an article about a gruesome murder. I don’t remember the names or the place. The long story short was that the killer hacked his victims in to little bits and shoved them in to suitcases in order to hide them. Google, in their wisdom, chose to place an ad for luggage on that page. Priceless.
Only slightly less wonderful than that was the ad that I found on my weblog today: “Meet Republican Singles.” Way to be, Google.