The Wire: D'Angelo Barksdale. A guy who never really had a chance, and was almost tormented by having just enough self-awareness to realize how trapped he was, and to want more, but too tied down by circumstance to escape his fate. Also, although they were not deaths, the departure of Michael and Dukie's subsequent fall to drugs was almost as bad. Even though both characters survived, when so many others hadn't, by that point in the show, the cyclical repetition of character arcs and the way they echoed the circumstances of Bubbles and Omar made you absolutely certain about the road ahead for each, and the inevitable end of that road, and how impossibly difficult getting off it would be.
For some reason, I could never get my head around the four boys in that season. I kept mixing them up mentally and kept forgetting who was who, which made the impact of their decline miss their target with me.
Maybe I watched too many episodes in a row (I did watch The Wire at breakneck speed), combined with the sheer amount of characters, all of them trying (and succeeding) to be memorable, that these four boys, who were introduced as just a group of boys within a larger group of boys who were playing hokey.
But D'Angelo: yeah. I've got to agree on that one. I didn't expect that to happen, not within the second season at least. I was expecting him to bite it at the threshold of freedom, or just past it.