Game: Donkey Kong (1981)

This ape has been a hero, a worrisome dad and a race car driver. However, his roots began as a boss. After absconding with a helpless princess, the giant monkey fends off her heroic plumber with barrels, vines and level after level of increasing platform difficulty. Being one of the original baddies in video games, Donkey Kong will always swing his way onto a great boss list.