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LeChuck - as seen in Monkey Island 1-4
Initially, Monkey Island’s signature baddie was just an angry ghost pirate stalking a girl who didn’t like him. It’s frankly astonishing how much oft-revised backstory the purportedly silly point-’n’-click adventures have since managed to shoehorn in. Whatever his past, his present seems to be climbing the ladder of evil: he’s escalated from ghost to zombie to demon, so perhaps he’ll be a Nazi or an advertising executive in the next game. One thing’s for sure: he’s both partial and allergic to voodoo, which in each game has been central to his latest cunning plan and his eventual defeat. He’s also one of very few villains to have emerged triumphant at the end of a game, trapping his nemesis Guybrush Threepwood in a demonic pastiche of Disney World at the end of Monkey Island 2.

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The Makron - as seen in Quake II and Quake IV
The giant enemy that’s actually a tiny man in a massive suit is one of those game boss stereotypes that just keeps on giving. In the case of the supreme leader of the Stroggs, even once his big robot body is destroyed, he turns out to be a brain in jar piloting a smaller robot that has a railgun for a head. A railgun for a head.

The Milkman - as seen in Psychonauts
It’s less the villain himself that makes this Psychonauts’ most bravura moment, but rather the level that is set inside his cracked mind. Escher-esque suburban streets spiral into bizarre ribbons that laugh in the face of physics, patrolled by wildly exaggerated G-Men unconvincingly posing as housewives, while cameras lurk in every hedge and stealth helicopters patrol the skies. It’s extreme paranoia made hilariously real, the kind of visual genius that only games can do. At the heart of it all lurks the Milkman himself, twisted personification of the anger of unhappy security guard Boyd. He attacks with bottles of exploding moo juice, solemnly intoning “I am the Milkman. My milk is delicious.”