I think the Unix entry is the funniest.

XML:
After describing the pistol, the bullets, and your foot in minute detail, you find out that you can’t actually get to shoot your foot. So you begin describing your disappointment instead.
Windows95:And the best one of all...
d:\setup
And lest we forget our roots...
>shoot self in foot
I don't see any self here.
>shoot me in foot
There is no you in the foot.
>shoot foot
I don't know which foot you're talking about.
>shoot left foot
You don't have the gun.
>get gun
You take the gun.
You're lantern just went out.
You are attacked by grues.
* * * YOU HAVE DIED * * *

And the best one of all...QuoteAnd lest we forget our roots...
>shoot self in foot
I don't see any self here.
>shoot me in foot
There is no you in the foot.
>shoot foot
I don't know which foot you're talking about.
>shoot left foot
You don't have the gun.
>get gun
You take the gun.
You're lantern just went out.
You are attacked by grues.
* * * YOU HAVE DIED * * *
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and then there is this gem:
http://maradydd.livejournal.com/293666.html
Keep going on to the next page. There is pages of comments where people contributed tons more.

Original address: https://www.donationcoder.com/forum/index.php?topic=5621.0