40. Monkey Island 2: LeChuck's Revenge (1991)

Final Level: Dinky Island
Why It Sucked: The Monkey Island games never shied away from breaking the fourth wall, but it just got awful when the ending to the second game revealed that LeChuck and Guybrush were actually two kids playing a game at a carnival. It was so bad that they disregarded it for Monkey Island 3 and pretended it had never happened.
How We Would End It: Well, if they did it for the lulz, we can't fault them.

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