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Instead of rehashing my Top 10 Boss article, I decided that highlighting excellent boss fights would be a better method of executing this type of feature.  Along with that, I'll also be picking the greatest enemies I've tangled up with in gaming.  Consider this the "Best of Villainy" feature. :)  As you may have gathered, this does have some spoilers.

BOSS BATTLE GREATS - Ganon (Zelda: Ocarina of Time)
Ganon is the epitome of excellent boss design.  He has evolved with the times, creating several of the best moments in boss history along his sinister path.  However, my personal favorite has been, and probably always will be, my first encounter with Ganondorf in Ocarina of Time.  How beautifully epic this battle was...I can visualize it perfectly even now.  Using Light Arrows, the Hookshot and the Master Sword in gameplay bliss-inducing unison to deliver the blows to the Evil King.  How the game seemed to be over once you escaped the crumbling castle.  
But then the intense scream of pain, the heavy, dense breathing, the pupiless eyes, the sudden appearance of the Triforce of Power, the overwhelming darkness Miyamoto and his team had created for the final fight with the King of Evil.  And how Ganon was born into the 3D realm...what an amazing cinematic.  The music is perfect.  The mood was fantastic.  The fight I still treasure.  And the way you finish him off...is just stunning, especially considering how the violence in Zelda never had felt so intense before that moment.  The way Link shoves the Master Sword into Ganon's head to finally subdue him...a haunting scene, one that would set precedent for the future duels with Ganondorf to follow.  A truly glorious battle, one that I will consider the most memorable that I've ever conquered.

ENEMY LEGEND - Medusa Heads (Castlevania series)
Arguably the most annoying enemy in gaming's long history, Medusa Heads exist merely to make the series' platforming all the more difficult to perform.  These diabolical beasts made traversing the NES games extra tough, especially with Simon/Trevor's tendency to fly backwards if struck by an attack.  As the Castlevania games evolved into Metroid-esque adventures, these foes became synonymous with the Clock Tower, the spike-filled hell hole that typically offers up the most platforming in modern Castlevanias.  And that's not all!  Some of these demonic Medusa spawn can also turn you to stone, which DOUBLES the damage you take on those nasty spikes (and commonly also lead to instant deaths...hope you saved!).  If there ever was an enemy that equals pure frustration, Medusa Heads would be my choice.  And that's why they are legendary...in their agonizing torture of players trying to make their way through already punishing platform hopping.