Ok. Ive thought long and hard on this one... I tend to spread evil around Skyrim like Johnny Appleseed, and came up with my top 3.
1) Saw an Ice and Fire Dragon fighting, got their attention, then brought them to Dawnstar and helped them slaughter EVERYONE. Except guards(infinite) and unkillables(bastards).
2) Random quest to go here and save this mans daughter from whatever. He wanted to join in my merriment of bloodshed. I cut his head off and proceeded to drop an imaginarey duece on him before drinking his wine and laughing as i forgot all about whatever he wanted me to deliver...? Find his sword? Ah whatever, not important.
3) I made a thief who only stole Sweetrolls. If I remember correctly, the last time I played him I had around 400ish laying in Breezehome.