Here's one from our local paper here in Lüneburg that made the rounds a few years ago. The story is about somebody deported to Auschwitz during the war. The ad is from our local gas company. Doh!
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I really find a lot of these seemingly based on keyword association (like the "teacher convicted of sex abuse/be a teaching assistant" example). There's probably an opportunity here for some better robots.

And what does this teach us, class? Ignore every message you recive and just do what you want.

I was at work the day the cnn.com one happened (in jason's original link). Good grief, you could almost HEAR the emails flying around.

It teaches us that some cats are Jesus wannabe's. As if they're not self-righteous enough...

There are certain Google keywords that probably should never be used in the Breaking News sections of news sites. I've been running a small Google ad on my blog for years (and just recently accumulated enough credits to get my first $100 check from them). I am no Power Adsense User and when I see some of the ads they 'match' to my jokey, often stream-of-consciousness posts, I wonder why I even bother.