Game: Final Fantasy IX (2000)
Love it or hate it, Final Fantasy VIII was kind of, um, heavy. So when it came time to prep the ninth installment, Square wanted to keep things jokey. The humor starts right from the opening scene of the game, which tasks your party with putting on a play called "I Want to Be Your Canary." It's a sort of surreal take on Shakespeare that acts as a battle tutorial and as a way to introduce several of the protagonists. The whole thing just exuded charm and let you know the kind of experience you were getting yourself into. Also, is the title a Stooges reference? Cool!