1. Conker (Diddy Kong Racing/Conker's Bad Fur Day)
Then: Apple-cheeked cutesy-pie, introduced in Rare's Diddy Kong Racing and set for wholesome adventures all his own. The slingshot-toting squirrel delighted(?) young audiences in the 1999 Game Boy Color adventure, Conker's Pocket Tales, and a full-fledged N64 outing, Twelve Tales: Conker 64, was on the way. "A Rare game about a cute little animal on a fetch-quest? Wonders never cease," we all sneered.
Now: "Screw it," said the ever-inventive Rare, "let's scrap this character and turn him into a foul-mouthed young lout on the hunt for girls and alcohol." The result, N64 classic Conker's Bad Fur Day, was heavy on pop-cultural callouts and bawdy humour. Advertised in Playboy instead of Nintendo Power--and, sure, lots of fun to play--the game reminded players that Nintendo/Rare were still capable of surprising you.