I'd say you would do the most damage with a Tank build as you progress through the levels (no pun intended). Most of the higher level players understand the importance of a tank, so if you FAIL in that role, the game is pretty much over. With no one to protect the squishies, it's game over. Although with a smurf account, I don't think many others at that level would even notice that kind of troll build. About the only thing I can come up with would be stacking boots, then laughing when people say it doesn't work. Tell them about the insane movespeed Rammus on Youtube or something.
IMO, I like AP Shaco as a sort of troll build. I'd imagine that would work WONDERS in the lower levels too. Pop JitBs, and wait for kills. Even if you just JitB some place stupid at level 1 while your teammates sit and wonder what is going on. Either that or use Teemo and shroom the crap out of an entire lane. Tell everyone the poison stacks or something.