Original Post
Just as the title says. The saddest achievements (in the Xbox sense) you've ever, uhm, achieved. For me, the saddest is Little Rocket Man in Half-Life 2 Episode 2. I spent all that time in the game escorting and protecting that little garden gnome. He became like a friend to me, a stalwart companion to both Gordon Freeman and Alyx Vance. And then, out of some twisted whim, the "good" doctor throws wee gnomey into the rocket's payload area and closes the door. I was devastated. All that time and effort keeping my gnome nearby and safe, and just like that he's gone. I almost cried. [crying] What achievements have made you sad?

- Portal - Heartbreaker