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.
I did the pickpocket back too!This ones more funny than evil but whenever I paid for pickpocket training from that beggar in Windhelm, I always immediately pickpocket my cash back.
Also Ulfr the Blind in White River Watch near Whiterun, killed his whole clan except for him. Imagine his horror when he tries to find his mates after they start smelling bad and realising he has nothing in life anymore...
Remind me to do that with my current Dark ElfHehe I snuck into the Battle-Born house at night and made them all murder eachother using fury spells. The children watched in terror as their father ripped their mother's stomach out. Muahahahahahahahaha