Bugs...
Big Rigs: Over the Road Racing has a few (google it if you don't know what I'm talking about :P)
The void in Daggerfall was pretty funny. And annoying.
The Championship Manager/Football Manager series has had a few fun bugs in it's time too. 3 year old players (or 300 year old players), strange transfer fees, players being duplicated, a player called 'DELETE ME PLEASE'... the newest football manager game seems to have issues with red cards. I seem to have 3 players sent off every week.
Frontier: Elite II, and Frontier: First Encounters had a few funny ones too. Collision detection is horrible, sometimes you'll just explode for no apparent reason. And there's that weird bug where you can warp for a huge distance for almost no fuel, ending up hundreds of light years away (I think it was because of floating point calculations or something technical like that).
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