Writing a Satisfying Ending – As Explained by The Princess Bride

I’ve lost count of all the story endings that I’ve read, watched or heard over the years. When I got into writing, I went back through some of my favorites with one goal in mind – why were they my favorites?

There’s some story endings that just stay with you, so that years after experiencing an author’s work you still might smile or feel sad at how things turned out. After looking at the stories that have I have loved over the years, I want to share the unofficial rules for what makes a great ending.

Let’s have some fun with this. I recently heard that a remake of the classic The Princess Bride is in the works – I hope not, I always thought the 1987 movie is perfect just the way it is. Watching this movie was a family tradition, it was watched when someone was sick or on a Sunday afternoon when everyone was in the house together. Eventually we could recite entire scenes to each other, and my sister even had an awesome “Mawage, is what bwings us, togetha, today” spin on her own wedding.

So without further ado – what makes a great ending?

You just shook your head! Doesn’t that make you happy?

The plan must go wrong: In every final battle, our brave heroes should always have a plan, no matter how crazy, as to how they will even the odds stacked against them. The fun lies in the fact that the plan should never go off without a hitch: something might get lost, a character might make a mistake, or a threat that had thought to be dealt with might re-emerge. In The Princess Bride, Inigo, Fezzik and the Dread Pirate Roberts/Westley must break into a castle guarded by 40 men, break up Buttercup’s wedding and escape. While Fezzik has a great time hamming it up as a terrifying version of the Dread Pirate Roberts, it all falls apart when the trio get inside the castle. The fact that Inigo runs off after the evil Count Rugen means that Fezzik gets lost and Westley disappears. Which leads us to the next point…

Hello. My name is Inigo Montoya. You killed my father. Prepare to die!

Secondary characters must get their time to shine: In this movie, the warm-up battles go to Fezzik and Inigo. The giant got to scare off 40 men while wearing a flaming robe, and Inigo gets a truly fantastic sword fight against his life-long nemesis, Count Rugen.

(side note: a childhood memory I have of this fight is when Rugen asks Inigo to spare his life, promising “anything you want.” The Spanish sword master replies with “I want my Father back, you son of a bitch” and stabs the villain. Dad turned to me and asked. “Would you do that for me?” I answered with a “Yeah!” and a lot of Father/Son victorious arm pumping ensued.)

The Hero and Villain must have their one-one-one moment: The reason why we have the plan go wrong and the secondary characters fight off their evil counterparts is so that the Hero or Heroine must be forced to risk everything on a final confrontation with the Villain. Luke Skywalker gambles it all on connecting with his father and defeating the evil Emperor. Jessica Jones has to summon her courage to face Killgrave, the man who once controlled her and could easily do so again. In The Princess Bride, Westley crawls through the castle to find Buttercup and face off against the arrogant Prince Humperdink. While this wasn’t the flashy battle seen earlier between Inigo and Rugen, the stakes had never been higher as the ultra-capable Westley was seemingly helpless to stop the Prince…

DROP. YOUR. SWORD.

The Hero must show something they’ve learnt, or overcome a major personal obstacle to succeed: This is where the Hero’s personal growth story should reach its conclusion. Every good Hero or Heroine should have a flaw, be it physical or emotional, and overcome it to secure their victory over the Villain. For an added bonus, this should reference earlier scenes of the story. In Aliens, the incredible Ellen Ripley must overcome the terrifying fear of the Xenomorphs that haunted her dreams at the start of the movie, going up against the Alien Queen to save the young girl Newt. Part of what made this scene satisfying wasn’t just that Ripley didn’t let her fear get the better of her, it was also that she used the Power Loader suit that she’d impressed the Space Marines with at the start of the story.

In The Princess Bride, Westley not only has to force his “mostly dead” body to stand, he knows from the previous interactions he’s had with Humperdink that the Prince is a coward who will give in the moment he’s threatened. A fantastic battle of wills ensues, although I don’t think I’ve ever heard any other protagonist win using the phrase “To the Pain!” For Westley, this is where he truly shows how much he has grown from a poor farmboy, overcoming death and staring down the most powerful man in the Kingdom.

The Hero must lose something in their victory: This leads us to the final rule – a good ending should have some kind of bittersweet edge. A worthwhile Hero or Heroine should never get their victory without paying some kind of a price. Frodo lost a finger and was both emotionally and physically scarred by the Ring of Power. Tony Stark died from radiation poisoning using the Infinity Stones to destroy Thanos. In The Princess Bride, Westley lets go of the role that had brought him wealth, talent and adventure, passing the title of Dread Pirate Roberts to Inigo. The loss, whether small or large, should free the Hero or Heroine from the circumstances they lived with while struggling against the Villain. Perhaps they’ll never be the same as they were, but the point is that the loss puts that part of the main character’s life behind them so that they can have their Happily Ever After.

That’s it for now, if you have any good story endings that these rules apply to then feel free to comment below, and please join me again on Thursday for another Words Are Weird webcomic!


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