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Essentially it means "is much better than" or "humiliates", and is most commonly used as a verb. "Pwn5" is [the ultimate] way to say "pwns", much in the same way "1337" is the ultimate way to say "l33t". The "5" represents the "s". It is also mid-way between 0 and 10, so is considered a direct hit between the eyes i.e. perfect. This stems from the origins of the word in online [multiplayer] gaming, where a [perfect shot] is respected. So if you want to be 1337, you should say "pwn5" instead of "pwns" ;) :P
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