Omikron009 said:
I always thought "my brother is an Italian plumber" from Borderlands was quit creative. For those of you that don't know, you get it for killing an enemy by jumping on its head. However, head jumps are so hard to pull off and do such minimal damage that you have to almost kill the enemy and then precisely jump on it. I think I got the achievement on a spiderantling.
It's funny, because I got that achievement totally on accident really early on in the game, and, being web-less at the time, had no clue what in the world I did to get it
Also, "I'm on a boat!"
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Red Dead Redemption has a couple of funny achievements, like "Dastardly" and "Heading South on a White Bronco," I found those two to be very amusing. Dastardly is great for being a nod to that classic spaghetti western villain maneuver, and "Heading South" simply for the pop culture reference, one that quite a few young'uns might not even get without a little research on their part these days.
The Orange Box had a smattering of very creative, challenging achievements "The One Free Bullet" (complete the episode shooting only one bullet) in HL2:Ep1 stands out as one with the most fun I've had tackling a challenge simply for the points.
Eldritch Warlord said:
"Flushed" from The Orange Box. You get it by killing an enemy with a toilet.
Pretty easy, except there's only one toilet in all of Half-Life 2 that you can actually pick up with the gravity gun.
I'm pretty certain that every toilet in the Nova Prospekt washroom where you fight the antlion guard can be yanked off the wall....and there's several of them.