I agree totally with Tim Bray's comments a couple of days ago that advertising on the web is out of control:
[Web ads] slither and shake and squirm and flash and jitter and morph and I’m gonna start bleeding from the eyeballs.
One of the best things about the web—and why Google Adsense is raking in the money—is that contextual advertising is so easy. Aside from Google's text ads, the best ads I've seen in a while are part of The Deck, a series of ads on design websites that are hand-picked by the authors as both quality products and quality advertisements (no flashing, well-designed, etc).
That said, it can be quite amusing when the automatic advertising selection gets the context completely wrong. Today while sending a link to the Hipster PDA to a colleague, an odd advertisement showed up beside it on 43 Folders.
The question is: who would buy a Blackberry, the ultimate in high-tech anti-GTD-ness, when they're reading about the ridiculously low-tech Hipster PDA?