My favorite achievement that I accomplished was Little Rocket Man in HL2: Episode 2. It was a pain in the dick, but I fought through it and was so happy to see the blurb pop up saying I got it. Too bad I lost it in some Xbox Live glitch fuck up. I probably had about 1600 gamerscore erased from the Orange Box, Mass Effect, and Assassin's Creed because of that... Oh well.
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