#50: Monkey Island 2: LeChuck’s Revenge (LucasArts, DOS, 1991) 

Right after that trip to the Governor’s mansion, you get the means to trigger one of the game’s moments of most surreal brilliance. Guybrush gets knocked unconscious by a tree-climbing fall, the world turns red, and he gets a vision. With the game’s newfound elan in mixing the hilarious and horrifying, that vision features the return of his parents, their transformation into singing and dancing skeletons, and Guybrush getting attacked by the Guybrush from The Secret of Monkey Island. Even his former self doesn’t like what he’s becoming.