Who: C. Montgomery Burns

What: Blocking out the sun/pissing off an entire town

When:May 21, 1995

Where: The Simpsons Season 6

Why its a great moment: Mr. Burns was always a bastard. Over the last twenty years he's blackmailed, smear campaigned, stolen money, posed nude, cancelled bonuses, racked up 342 environmental safety violations, and run over kids with his car. And by "last twenty years" I mean "first two seasons."

His wikipedia article reads like an application to The Legion of Doom. Wizard magazine lists Burns as the 45th greatest villain ever, beating names like Brainiac, Venom, Catwoman and Megatron.

Still, Burns's shining moment was in the season 6 finale. After destroying his enemies; the retirement castle, Moe's Tavern and Springfield Elementary School, he crossed the line between regular villainy and cartoonish supervillainy. "Since the beginning of time man has yearned to destroy the sun. I will do the next best thing: block it out."

He built a freakin machine to block out the sun, casting the entire town into eternal darkness! Holy crap!

But the real icing on the Screw You Cake was his response to the whole town threating to kill him. So what do you do when the entire town wants you dead? You show up at town hall where they're all packin' heat, and egg them on. "You all talk big, but who here has the guts to stop me?"

What chrome-plated balls on that guy! The whole town is really planning to murder him in the streets and he shows up one middle finger raised high, the other hand defiantly on his crotch!

And for that, we salute him.

Got a suggestion for one of villainy's greatest moments -- in comics, movies, books, TV, video games, whatever? Drop us a line at submissions@the-iss.com.