These were some high-quality entries. I had a lot of fun running this contest and I hope you all had as much fun participating in it. However, I must admit to having three regrets about this contest:
(1) That none of these games actually exist.
(2) That I couldn't compete in it. Although I didn't let that stop me from whipping up a couple of Dragon Warrior edits:

(3) That I can only pick one winner. So even though you don't get anything for it, here's the list of Honorable Mentions:
JrnymnNate's wirthling/Deus Ex box. Fits nicely, looks natural.
boorite's Gauntlet parody. I have a soft spot for that Gauntlet warning voice. "Tobor cornholed the food" is classic.
wirthling's Double Drag Queen box. Excellent concept, excellent editing job.
Spankling's Diablo III character screen. Boorite as the paladin is perfect.
TheElPaso's The Perms box. As funny as it is disturbing.
DexX's wirthling-as-Shodan. I've never played System Shock, but judging by the link you gave us, it's an incredible likeness.
But when all is said and done, I don't see how I could fail to give the victory to Drexle. Clearly this contest was calling his name. I could list all the entries I think he deserves to win for, but it would be quicker just to tell you to re-read this thread. So, although we don't usually do it this way, I'm awarding him the (figurative) trophy based on the collective strength of all his entries. If you don't like that, then pick your favorite of his entries and pretend he won for that one.
Thanks to everyone for the great artwork. Even if you didn't make the short list, you still made me laugh.
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The what mentioned above is total fiction. Please don't take it seriously!