Spite Houses

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A spite house is a building constructed or modified to irritate neighbors or other parties with land stakes. Spite houses often serve as obstructions, blocking out light or access to neighboring buildings, or as flamboyant symbols of defiance. Because long-term occupation is at best a secondary consideration, spite houses frequently sport strange and impractical structures.

Boing Boing has an article about spite houses. LINK: The Presurfer

The Annoying Orange

An Orange annoys the hell out of his friend, Apple. LINK: Youtube

The 10 Most Irritatingly Impossible Old-School Video Games

Battle Toads is the number one on the list.
The premise:
Two anthropomorphic toads, who are in no way in violation of copyrights which may or may not be had on other anthropomorphic baddy-fighting creatures, attempt to rescue their friends from the evil Dark Queen.
Why it was infuriating:
The potentially awesome hover biking is made somewhat less so when you realize few players were able to last more than six seconds before smashing into a wall or plummeting to their death. With each checkpoint bar the player reached, a small ball of hope grew inside of them--only to be smashed on the ensuing wall seconds later.
There is also videos you can watch when you go to the link.