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Rag Doll Kung Fu is a pretty strange game.
http://ca.youtube.com/watch?v=frYZu_1mhXA
Prey had it's moments of pure insanity.
Psychonauts is not only weird, is also one of the best games ever (Goggalor rules)
Wolfenstein 3D + Spear of Destiny, they surely have the weirdest bosses, beasts, giant nazis and so on....
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bpops: Eternal Darkness
Psychonauts

The Milkman Prophecy... God I love Psychonauts.
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bpops: Eternal Darkness
Psychonauts
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Aatami: The Milkman Prophecy... God I love Psychonauts.

Oddly enough, Psychonauts seems completely normal to me.
Weird Dreams seems to tick all the right boxes in that regard:
http://www.youtube.com/watch?v=z1rhvFW3Lbo
weird in a brilliant way : Toonstruck :D
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DrWevil: weird in a brilliant way : Toonstruck :D

Awesome game. FLUFFY BUN BUNS!
Morrowind!
At the beginning of the game, I walked out of the first city and suddenly heard a "...aaaaah..". I looked around, but nothing was to be seen, while the sound grew louder and louder. And suddenly it made a sound like *scrunch* and a wizard dropped from the sky and splashed right in front of my feet.
Searching his body revealed a short note, which read:
"I believe I may have found the correct forumla for the spell I am developing. With it, I will be able to travel great distances without the need to pay others for the service. I believe I have worked out all of the possible complications. It will allow me to leap great distances, covering many hundreds of miles."
In addition he carried some potions which enabled you to jump over half the island .. one of the funniest and weirdest encounters I ever had in a game :-)
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Pantalaimon: Morrowind!
At the beginning of the game, I walked out of the first city and suddenly heard a "...aaaaah..". I looked around, but nothing was to be seen, while the sound grew louder and louder. And suddenly it made a sound like *scrunch* and a wizard dropped from the sky and splashed right in front of my feet.
Searching his body revealed a short note, which read:
"I believe I may have found the correct forumla for the spell I am developing. With it, I will be able to travel great distances without the need to pay others for the service. I believe I have worked out all of the possible complications. It will allow me to leap great distances, covering many hundreds of miles."
In addition he carried some potions which enabled you to jump over half the island .. one of the funniest and weirdest encounters I ever had in a game :-)

Oh, yes, I remember that. Right outside of the starter town, too. I thought it was funny so I tried it myself. The results were seeing the most breathtaking sight in the entire game, followed by a crunch as my character landed and sustained damage more than any mortal could take. :P
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MinigunFiend: The final boss in Half-Life.
What the hell was that thing anyway?

Oh yeah - the practically unkiilable fetus. Who thought that was a good idea?
I did. Still do.
Killer 7 was definitely a weird game, it's a shame it was such a god awful gameplay experience.
Vangers was pretty damn messed up. Killer 7, always good for a "OK... wait, what?" moment. Psychonauts wasn't really all that deranged, just off-kilter a tad. Eternal Darkness had a nice edge of "Is it real?", and the immersion techniques were top-notch.
Now, You want really twisted, play Dreamweb. By the end of that you're sitting there going "... Que?"
Or try jumping into a nice, old game called Tass Times in Tonetown. First-person text/mouse adventure game. Really deranged.