Here are my current selections in each category. Was actually really difficult to choose each game.
Test of Time
Deus Ex: Game of the Year Edition, because of reasons
I’m Not Crying, There’s Something In My Eye
Papo & Yo, especially if you understand the metaphoric nature of the game and what it actually represents
Just 5 More Minutes
Sid Meier's Civilization V, the ultimate time sink of a game
Whoooaaaaaaa, dude!
BioShock, that twist, yo
Villain Most In Need Of A Hug
Borderlands 2, Handsome Jack just wanna be loved, aggashame
Game Within A Game
The Witcher 3: Wild Hunt, I hate Gwent, but I cannot deny it's impact on the world. It's a really impressive achievement
I Thought This Game Was Cool Before It Won An Award
Factorio, I got this while if was still in alpha, saw it being played by a YouTuber, way before it's Steam release.
Best Use Of A Farm Animal
Stardew Valley, those cows are adorable!!
We Didn’t Think Of Everything
My Award is called the "Out Of This World" Award, and it goes to Kerbal Space Program, because it's literally about getting out of this world, and it's just out of this world amazing. I'll stop saying that now.