The Expanded Ultimate Story Checklist: Does the ending tip toward one side of the thematic dilemma without entirely resolving it?

Your theme should take the form of an irresolvable dilemma, so you should give both sides equal weight for as long as possible until the climax. The trick is to come up with a finale that addresses the conflict and makes a concrete statement about it, without definitively declaring one side right and the other wrong. 

Each of the first three seasons of Lost has a powerful overarching theme:

• Season one: our future is dictated by our past versus our future is a blank slate 
• Season two: faith versus skepticism 
• Season three: strict, safe order (the Others) versus chaotic, unsafe freedom (the crash survivors) 

At the end of each season, the characters advocating one side of the debate are proven “right.”

• Season one: The characters find ways to move on from the past, and even sing “Redemption Song” together on a boat. 
• Season two: We find out Locke was right to have faith in the button, and Jack was wrong when he said it did nothing. 
• Season three: The chaotic makeshift community of the crash survivors proves to be more sustainable than the cultlike Others. 

But in each case, the victory is ironic and ambiguous. A statement is made about the dilemma, but it’s not permanently settled.

You have something to say, but you don’t have something definitive to say. You have a point, but your point is untidy. You’re leaving room open for uncertainty and ambiguity, because that multiplies the meaning.

Let’s return to the stories we looked at before. Each has an irreconcilable thematic dilemma, and five of them tip toward one side in the end, but not definitively:

• Casablanca: Patriotism is better than love, but it’s a painful decision. 
• Beloved: Sethe will never know whether enslavement was better than death for her daughter, but she warily accepts that self-forgiveness is better than self-accountability. 
• Harry Potter and the Philosopher’s Stone: Justice is better than peace, but it comes with dark consequences. (Harry not only kills Quirrell, but he condemns Dumbledore’s friend Nicholas Flamel to death by destroying the stone.) 
• Iron Man: Yes, societal responsibility is ultimately somewhat more important than individual achievement, but Tony still wants to be a badass all the time, not a do-gooder. 
• An Education: Yes, living up to one’s responsibilities is somewhat better than a life of excitement, but we sense she doesn’t really regret her dalliance and still longs to be more sophisticated than her parents. 

But the other three have interesting variations:

• In Groundhog Day, one of the contrasting values in the thematic dilemma is clearly superior to the others. Phil concludes that acceptance is almost entirely better than ambition. 
• Silence of the Lambs ends with its moral dilemma still totally unsettled. Neither Clarice nor the audience can decide at the end whether it was worth it to work with one monster to stop another. 
• Sideways pits Jack’s boundless optimism versus Miles’s clear-eyed cynicism, but each man achieves his own goal by reverting to type at the end and fails to influence the other. Jack’s outrageous, optimistic lies pay off for him, and Miles’s cynical honesty pays off for him. The conclusion looks askance at both of their philosophies but refuses to privilege either one over the other. 

So this rule isn’t universal: You can resolve the dilemma definitively, tip to one side without resolving it, or leave it totally unresolved, but the middle option is the most common and usually the best bet. You have something to say, so say it, but you don’t want to take away from the fundamental power of the irreconcilable dilemma.

Rulebook Casefile: The Irresolvable Thematic Dilemma in Rushmore

When I was trying to identify Max’s false statement of philosophy in Rushmore, I settled on this exchange: “What are you going to do?” “The only thing I can do: try to pull some strings with the administration.” For this corrected statement of philosophy later, I chose “I’m just a barber’s son.” But what about the movie’s most prominent statement of philosophy?

Max’s obsession with Miss Cross begins when he’s reading a book on diving and he finds that she has jotted down a Cousteau quote in the margins: “When one man, for whatever reason, has the opportunity to lead an extraordinary life, he has no right to keep it to himself.” Is that statement proven to be false or true?

This brings us to another rule: the ending should tip towards one side of the thematic dilemma without resolving it entirely. The central thematic dilemma in this movie is ambition vs. acceptance, and ultimately it tips towards acceptance, but that’s a hard choice.

Anti-ambition movies are few and far between. America worships ambition and our movies do the same. It’s hard not to root for Max’s wild schemes. It’s painful to watch him pour so much energy and optimism into things and then admit that his work is too ambitious and ultimately not very good. We want and expect to see those qualities rewarded.

And indeed the movie only barely tips towards acceptance. He accepts public school, and gives up on Miss Cross, and admits to everyone that his dad’s a barber, but he’s still making overly ambitious plays and collecting acolytes. So is that quote false or true? Max is not as extraordinary as he thought he was, but he’s certainly unique. How will his life change for better or for worse if he learns to keep that to himself, as least some of the time?

Most movies sell us the wish fulfillment message that there’s always something more waiting for us if we’re willing to be bigger and bolder. This is one of the few that raises the possibility that we may be happier and healthier if we learn to accept a life that’s smaller. It’s a painful realization, and that pain gives this movie its emotional punch.

The 40 Year Old Virgin	YES. Respect for women and need for sex remain equally important, self-sufficiency is not as good as co-dependent love.
Alien	NO. this movie resolves its moral dilemma far more definitively than most movies: corporations are completely evil, quarantine is totally sacrosanct, self-preservation is entirely better than protecting new life-forms. Personal safety is entirely better than job loyalty. This is fine: horror movies are less ambiguous than most genres.
An Education	YES.  Responsibility is ultimately better than the glamour. (But given that everything turned out okay, you suspect that she doesn’t really have any regrets)
The Babadook	YES. Very much so.  Grief must be nurtured but controlled.
Blazing Saddles	YES. Solidarity is better than individualism, but Bart is still too discontent to be part of the community he created. Winning people over is better than standing up to them,  but both must be combined.  Anger is better than subservience, but must be controlled.
Blue Velvet	NO. Not really, we still can’t decide which is worse: naivete or cynicism. Jeffrey has decided to restore his life to a level of naive idealistic artifice, but it is merely a mask for his yawning chasm of dark cynicism, and we sense that he’s still utterly torn between these two unpleasant choices.
The Bourne Identity	NO. It tips fairly definitively: conscience is proven to be clearly better than duty. They could have attempted to make this more ambiguous by pointing to important missions that won’t get fulfilled due to Bourne’s crisis of conscience, but this is one case in which ambiguity would feel like the weaker choice: We see that the “vital CIA mission” Bourne was accomplishing was the execution of a deposed dictator and former CIA asset who was going to write a tell-all memoir. In this case, the need to show an irresolvable dilemma is trumped by the need to show the way the world works. We know that the CIA always claims that their dirty tricks are justified by their vital missions, and we also know that that always turns out to be bullshit. Indeed, the hapless reboot The Bourne Legacy does have a “but what about the vital missions?” scene, and it feels cheap and phony.
Bridesmaids	YES. It’s ultimately probably better to prioritize finding a romantic life partner over holding onto a long-distance friendship.
Casablanca	YES. it comes down strongly on the side of country, but love is clearly more appealing.
Chinatown	YES. It is better to honor the past than shoddily and unjustly build the future.
Donnie Brasco	YES.  Family loyalties are ultimately more important than work loyalties.  He chooses to go back to being a cop, a husband, and a father, but he still feels like a gangster inside and he can’t forgive himself for getting Lefty killed.
Do the Right Thing	YES. It’s still split pretty much evenly at the end, as evidenced by the conflicting quotes from Martin and Malcolm
The Farewell	YES. Happy lie is seemingly better, but we’re not sure of that.
The Fighter	YES. Family and independence must be kept in balance.
Frozen	YES. Family is better than independence, but both are important.
The Fugitive	YES. justice is better than law, but the solution is to forcibly bend the law back toward justice, rather than abandon law altogether.
Get Out	NO. it tips definitively: Vigilance is entirely great, cooperation is fatally naive.
Groundhog Day	NO. It’s pretty definitive. Phil concludes that acceptance of one’s circumstances is pretty much entirely better than personal ambition.
How to Train Your Dragon	YES. Justice is ultimately more important than loyalty to family, but it’s an impossible choice so the two must be reconciled. The other dilemma is split: They’re able to make peace with most, but have to kill the one who won’t make peace.
In a Lonely Place	YES. self protection is better than sacrificing for love, but it’s a painful choice.
Iron Man	YES. Societal responsibility is clearly better, but Individual achievement is still pretty cool.
Lady Bird	YES. She chooses ambition but realizes she also needs to accept that she should have been more loving towards her mom and her town.
Raising Arizona	YES. Settling for a meager legal life is better, though disappointing.
Rushmore	YES. Acceptance is better than ambition, but ambition still looks pretty great.
Selma	YES. Moderation works, this time, but we sense that DuVernay thinks other methods might have worked, too, and maybe we still have severe problems today because the movement was too moderate.
The Shining	NO. As in many horror movies, it tips overwhelmingly: Family is better than masculinity, mother is better than father, self-protection is better than loyalty to parents, moving on is better than making it work, trusting yourself is better than trusting your parents.
Sideways	YES. It looks askance at both of our heroes’ philosophies (Jack’s boundless optimism vs. Miles’s clear-eyed cynicism), but refuses to privilege either one over the other. Ironically, each man achieves his own goal by reverting to type at the end and fails to influence the other one: Jack’s outrageous positive-thinking lies pays off for him, and Miles’s cynical honesty pays off for him.
The Silence of the Lambs	YES. It’s implied that it was probably worth it, (maybe it would have felt very different if we ended on Lecter killing an innocent family, for instance)
Star Wars	YES. Spirituality is better than technology, but even more dangerous in the wrong hands.
Sunset Boulevard	YES. dignity is somewhat better than success.