15 Movies That Can Teach You Everything You Need To Know About Character Dilemma

8. The Celebration (Thomas Vinterberg, 1998)

The Celebration (1998)

What it can teach you: Choose the right scene.

Thomas Vinterberg´s “The Celebration”, can be best described as a choked laugh, spontaneously smothered by a raw look, because this is exactly how you feel when watching it, especially, whenever you intend to laugh at a scene of the movie, which you are not entirely sure is supposed to be funny.

At the sixtieth birthday party of the patriarch of a Danish family, the eldest son (Christian) reveals all the corrupt and painful secrets surrounding the family– abuse and rape. In front of all the guests and distant relatives, Christian raises his glass, and calmly offers a toast for his father, who is also the man who raped him and his sister, when they were just children. The guests make an effort to drown the accusation with fake laughs and banal change of subjects, but by the second time Christian raises his glass, all hell lets loose.

With the rap of a spoon against a glass, begins a dilemma of catastrophic proportions for all the family members, some household employees, and a couple of drunken guests. Should they believe Christian´s words or not? A perfect scene introduces a perfect dilemma. All the character´s lives will forever be transformed as they spin down, without control, into an evening of chronic revelations and farcical wounds.

If you have spent enough time hurting your head with rewrites and rewrites, with the only purpose of nailing the dilemma of your story, make sure to choose right scene to introduce it as well.


9. Million Dollar Baby (Clint Eastwood, 2004)


What it can teach you: Dilemma is all about moments of wisdom.

In Clint Eastwood´s boxing homage, Million Dollar Baby, near the end, there is a superb moment of ordinary quietness between Frankie (Eastwood) and Eddie (Morgan Freeman). They share a silent conversation, plunged deep inside the slashing darkness of their gym. It’s a loud ode to forgiveness whispered in small mumbles.

At the same time, Maggie (Hilary Swank), Frankie´s pupil, friend, daughter (there are no correct labels for this relationship, since it transcends all of them) lies on a hospital bed after being struck down by “the Bear,” and breaking her neck with a wooden stool as a result of an unfair boxing match. Her legs have been amputated, and she now floats in a gaseous state between consciousness and unconsciousness, due to the cocktail of sedatives they are giving her, to keep her from attempting suicide. In a last effort to articulate, Maggie asks Frankie to help her, to finish it all, to kill her.

By the time Frankie and Eddie are sharing the previously mentioned scene, Frankie remains hesitant and undecided towards the action he should take in order to solve the main dilemma. Does he provide Maggie a humane, quick death despite the risk of being accused for her murder, as well as definitely losing his favorite person in the world, or let her live until she gradually rots in that hospital bed?

It is Morgan Freeman´s character, who, with a beautiful line, “If she dies today her last thought will be: I think I did all right,” transforms Frankie´s doubts into a resolved matter. With that brief encounter, our main character undergoes a moment of wisdom; he decides to help her.

With great dilemma comes great wisdom. Any good character, in any storytelling medium, has the right to a moment of wisdom. Be it long and harsh or instant and subtle, it must be a moment of profound recognition in which both the audience and the character are able to understand the impact of the actions that must now taken.


10. Match Point (Woody Allen, 2005)

match point

What it can teach you: Dueling desires. Why can´t the character have it all?

If a man is asked to be the best man at his best friend´s wedding, and the godfather at his nephew´s christening, and both ceremonies are on the same day, at the same time, at two different locations, well…you may say the story has a good dilemma for the character. However, if the story unfolds in a positive manner when the man tricks everybody to have both events at the same place, well, now it sounds like a funny kind of a movie if you got nothing else to watch, but nothing you´ll remember after dinner. Why? Because the dilemma of the story has now solidified into dog crap.

Match Point was the sexy overture to a new kind of Woody Allen genre. It marked the beginning of his cinematic tour de force around Europe, but mostly, it proved the genius of a seventy-something year-old director, we all thought did not have the strength, nor the ability to continue shining and burning a creative light. Young, fresh, and smoking hot, Match Point is a lesson in storytelling, because it exquisitely (and painfully) exposes a simple character rule: The character can never, and I mean NEVER, be able to get away with both options, due to his dueling desires, presented in a dilemma..

Dueling desires means that the character desires both choices equally, but such desires repel each other like magnets with the same electrical charge.

Allen juggles with our expectations towards the character of the film, a beat-up, ex-tennis player, now married to a wealthy English woman, but having an affair with an unemployed American actress, as we see him struggle through the burning desires of choosing one of the two lifestyles he would have with each woman.

If you haven´t seen this movie, when you do, and you get to the part where he makes his choice, you´ll feel a skinny, icy finger running down your spine.


11. The Lives of Others (Florian Henckel von Donnersmarck, 2006)


What it can teach you: The strength of a dilemma depends on how much the character´s convictions are put to the test.

The Lives of Others! Where do I begin? First, it seems as if the movie was adapted from a very complex espionage best seller, but it was not. Florian Henckel von Donnersmarck originally wrote it for the screen. In the hands of a different filmmaker, the genre of the movie would have overpowered story and character. Von Donnersmarck trusts only authority of human contradiction to support the film. It is not a formula movie. It is not about spies, not about socialism, not about sacrifice or betrayal. The Lives of Others is a movie about human subtraction, about human internalization.

The story is not complicated. It takes place in East Germany before the fall of the wall. Gerd Wiesler is a member of the Stasi police. He has a mission: To spy on playwright Dreyman and his lover, actress Christa-Maria, to prove that he is not loyal to the government ideals. He finds evidence to incriminate them, but chooses not to provide it. Why? The couple has changed his convictions along the way.

The movie asks for our sympathy, but there is nothing sympathetic about our main character. A machine-like man, dressed in grey, married to the most frigid and coldest of wives: his nation. Where the movie shines beautifully is in its ability to show change, through the actions of an emotionless character, whose convictions are imploding with disastrous cracks, as he continues to investigate this couple.

Each dilemma that he comes across (showing the evidence to destroy the lives of these individuals or not) has the delightful function of testing the beliefs of a man who was taught and ordered to think, but never to feel. There are no inner monologues, no small indications of what crosses his mind. No. There are only choices.


12. 4 Months, 3 Weeks, 2 Days (Cristian Mungiu, 2007)


What it can teach you: Dilemmas must go beyond the superficial layers of a simple “problem.” THERE ARE ALWAYS TWO CHOICES TO MAKE, AT LEAST.

Bad movies introduce characters with simple problems that have no challenges in store for them. Great films, on the other hand, raise the bar by presenting two or more choices where there is always something to lose no matter the decision taken by the hero.

4 Months, 3 Weeks, 2 Days is a great film from which to learn this principle. Yes, it is a murky, tripping balls kind of an experience that could also be described as the most fucked up waiting game ever. Throughout the film, we follow Otilia, a foreign student living in Romania in the ‘80s, as she tries to arrange an illegal abortion for her friend, Gabita, who by the way, is also the most passive-aggressive, maddening roommate anyone could want.

What should be a simple day of confirming hotel reservations, meeting up with a dubious “doctor”, and getting the hell out of that situation ends up transforming into a maleficent voyage through the nine circles of Hell, as we literally “wait” along with Otilia, while the circumstances unfold, little by little, into catastrophic events.

When the aforementioned doctor turns out to be a complete son of a bitch, Otilia must decide between having sex with the bastard, who has now refused to perform the abortion, because Gabita is more than three months pregnant, or let him leave and watch her friend become a single mother. Apparently, in 1987 Romania, being a single mother was worse than let’s say…a death sentence.

Two choices; no easy way out. Oh, yeah, did I forget to mention that Otilia has a boyfriend, and she is supposed to meet him at his mother´s birthday in less than two hours?


13. The Dark Knight (Christopher Nolan, 2008)


What it can teach you: Dilemma must always mean SACRIFICE!

Christopher Nolan´s second film in his Batman trilogy, deals with an ethereal, yet universal kind of dilemma: The dilemma of identity. Is there nothing else beyond heroes and villains? Can we be something more? If so, how can my actions transcend those labels?

With The Dark Knight, Nolan liquefies the meaning of what makes a superhero “super” into a warm soup of psychological drama. The best part is that he feeds it to the audience in small doses of character disintegration.

This film is a strange lesson in screenwriting, in which Christopher and Jonathan Nolan refuse to construct or build a character. Instead, they decide to disintegrate him into little pieces of contradictions. Batman and Bruce Wayne are both prisoners of the same conscious man. A man, who, in this film, is stripped down to his very core and forced to understand not only himself, but also the communion of his alter egos, through a package of figurative “shit hit the fan” kind of dilemmas: from deciding between rescuing the woman he loves or the man who could actually save Gotham city, to throwing the “Joker” off a building or not. Jesus! Even Alfred gets a punch in the guts when he has to decide between delivering the last letter Rachel wrote to Bruce! Let’s not focus on Alfred, though.

The point is it is not about superpowers. It’s about super-choices. Layer by layer, Nolan peels our main character until he remains naked (figuratively speaking) in front of the truth. In front of the final, ultimate, and father of all dilemmas: “The only way he can be a true hero is by becoming the villain,”… SACRIFICE! Is there something greater than heroes and villains? Yes! There is!


14. Toy Story 3 (Lee Unkrich, 2010)


What it can teach you: Dilemma must lead to a transcendental finale.

If, by the end of each of the movies from the Toy Story trilogy, Woody appears to be such an endearing character–a prototype of the old-fashioned American cowboy who possesses nothing but righteous qualities–it is due, in most part, to the degree of selflessness the writers injected in the character over the course of the three films.

There is no fun in watching a character make the right choices repeatedly until the credits start rolling. No, no, no. In fact, what separates a good movie ending from a transcendental one is precisely the recognition the character has in order to make the “right” choice when everything appears to be lost. No transcendent finale will come, if it isn´t delivered from a choice that makes the character win something, and lose something equally important by the end of the movie. This is where Toy Story 3 excels and distinguishes itself from the rest.

Imagine if the toys would have met their end in the flaming mouth of the incinerator (lose-lose situation). That is just plain ass depressing. Now, imagine if by the end, Andy decides to take all the toys with him to college (win-win situation) that is just plain ass forgettable.

There were plenty of finales I am sure the writers thought to incorporate before reaching the perfect one, and what a perfect one! In the last minutes of the film, Woody discovers the true meaning of family, when watching Andy and his mom hug in a ceremonious goodbye ritual. He makes one last choice: Give up the person he loves the most for the goodness of his true family, the other toys.

This is a one kind of an ending that makes you want to re-watch the movie every time you catch it on T.V., the kind of ending that leaves you hanging with contradictory emotions: “I am so happy for Woody and the toys; they have a new kid that will play with them, but, oh, god! Woody and Andy will never see each other again.”

If your ending is far from being transcendental, you are probably not giving your dilemmas the attention it needs.


15. A Separation (Asghar Farhadi, 2011)

A Separation

What it can teach you: The main dilemma must open the door for other subsequent dilemmas.

Every once in a while, comes a movie so pleasantly absorbing, that you feel you could just die a peaceful death right there in the thick darkness of the movie theater, and as the lights go up, so does your soul. That is what happens to you after watching Asghar Farhadi´s A Separation.

The film is a domestic drama. Disregard the fact that the story takes place in Iran. It´s about regular people wrapped in a macabre situation, so annoyingly common, that it makes you wonder: “Shit! What would I do in this same position?”

The film opens with our main couple filing for divorce (Nader and Simin). She wants to leave Iran with their daughter; he does not. He can´t. His father has Alzheimer’s and nobody else can take care of him. It´s a starting dilemma in its own terms, since evidently, they still love each other but their egos are on the way.

The main dilemma however, arrives when Nader hires a pregnant woman to take care of his father, while he is at work. After a negligence that almost costs the life of the old man, Nader fires her in a nerve-wracking, heated argument, pushing her out of his home. The next day, he finds out the woman has been hospitalized, and she has lost her baby. Not only that, but the family is accusing him of murdering the unborn child.

The film has a mirroring effect. It holds the reflection of tarnished men and women high enough, for everyone in the audience to ponder what is like when you have no resources left but to scavenge for a slight piece of dignity, in a situation that is everything but dignifying. Every single character in the movie faces a dilemma, and, when forced to face that dilemma, they will most likely provoke another dilemma, for someone else to suffer it.

Author Bio: Miguel Guerrero Becerra is a Mexican filmmaker who specializes in developing webseries. He is also a film instructor at two universities in Mexico. His favorite class to teach is writing and directing for television.