In most stories, the hero is the underdog battling against injustice created by a super-powerful villain. In these common types of stories, the hero typically wins at the end. However, what if you want your hero to lose?
There’s a big difference between your hero and your villain. Your hero typically changes during the course of the story, learns a lesson, and based on that new lesson, your hero is able to defeat the villain.
(One notable exception to this is “WALL-E” where WALL-E pretty much stays the same character throughout the story, causing others to change as a result of their interaction with him. The writers modeled WALL-E after Charlie Chaplin, the lovable tramp who would remain basically the same person but change the lives of everyone he met.)
The reason your hero can win in the end is because he or she is willing to change. The reason why your hero can lose in the end is because he or she is not willing to change.
In “The Ladykilllers” remake starring Tom Hanks, Tom Hanks plays the hero who is actually the villain. His “villain” is actually a kindly old lady who opposes him. In a traditional story, the hero is the underdog and the villain is all-powerful. Switch the roles around and in “The Ladykillers,” Tom Hanks is all-powerful and the old lady is the underdog. Despite being the “hero,” Tom Hanks still retains the power of the typical villain.
In “The Ladykillers,” Tom Hanks recruits a bunch of misfits to tunnel into a casino, rob it, and then cover their tracks. To dig this tunnel, they have to dig through the tunnel in the old lady’s basement and keep her from discovering what they’re really doing down there.
Throughout the story, Tom Hanks remains the same shifty, clever character that he was at the beginning. Because he doesn’t change, he fails in the end. The old lady also doesn’t change, but she technically “wins” in the end even though she doesn’t know it.
If you want your hero to win in the end, your hero must change. If you want your hero to lose at the end, your hero does not need to change. In fact, the hero who loses does so because he or she does not learn an important lesson. The penalty for not learning is losing.
Making your hero lose is rarely a satisfying ending because we’re rooting for the hero and nobody wants to see their favorite lose just like nobody wants to see their favorite sports team lose. Sometimes a better approach is to make your hero lose, but actually win in an unexpected way.
In “Rocky,” Rocky actually loses the fight, but because he stayed on his feet the whole fight, he wins the respect of a nation and his girlfriend, which is what he really wanted after all.
In “Thelma and Louise,” the two women die in the end, which can hardly be called a happy ending. Yet because they refused to be arrested, they actually “won” by maintaining their freedom.
Sometimes the hero wins, sometimes the hero loses but the loss turns into a win. And sometimes the hero just loses altogether, which usually only works in dark comedies like “The Ladykillers” or “Dr. Strangelove.”