I chose the golden days of N64 and Playstation 1 for my piece. Because I
know not everyone knows these characters, I'll list'm:
"Prune Juice" Moonraker Elite (b) from Goldeneye 007, Spyro from the Spyro games, Crash Bandicoot (and the Tiki Mask thinger) from the Crash Bandicoot Games, and Link from Zelda (specifically Ocarina of Time). Also featuring one of the versions of the winning screen from the Mario Party 2 mini-games!
I had a hell of a lot of fun playing these games when I was younger. I always played as Prune Juice with my group of friends (everyone had that group of friends y'played 007 with), coasting as Spyro, running away backwards from an encroaching obstacle as Crash, and riding the pony as Link (I probably didn't actually finish that game.. riding the pony was the highlight for me, hence fourth place).
.. and now I can go back to drawing TF2 fanart.