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


If character choice drives the story, dilemma is the storytelling element that engages us to it. Choice will only be as good as the situation that precedes it. If choice is a response to your character´s personality, then you can only truly know your character, if you introduce the proper challenge for him to confront.

Here is a list of movies that can teach you everything about why and how good dilemmas should be created, introduced, and used as one of the most important storytelling elements, in order to create a great film.


1. Casablanca (Michael Curtiz, 1942)


What it can teach you: Dilemmas must have clear stakes and consequences. How much can the character lose? How much does it mean for him to lose it?

Rick Blaine (Humphrey Bogart) should have been named the president of humanity after that last scene in Casablanca. The ending of this film is like a delicate roar, so profoundly moving in a private, soundless manner, so filled with obtrusive glances of glimmering hope, in an overall, foggy and depressing finale. Yes, he lets Ilsa (Ingrid Bergman) go. He will probably never see her again, but he has given her the chance of a dignified life, which he just cannot offer her.

The dilemma that Rick faces in Casablanca when Ilsa returns to his life is so carnivorously aggressive due to the significance of their relationship and what it has done to him once it was over. There is too much on the line for Rick, whether he decides to help Ilsa and her husband by giving them the papers of transit or not. Especially, when we learn how much Ilsa still means to him.

There is nothing fun in watching a character win, if he hasn’t lost enough beforehand. That´s what dilemmas are for! However, how much a character is able to lose does not mean anything in a dilemma, if we, the audience, are not aware of how much it means for the character to lose it.


2. The Bicycle Thief (Vittorio de Sica, 1948)


What it can teach you: The strength of the dilemma depends on how much the audience is rooting for the character. No matter the morality of such character, the audience must find empathy in his decisions.

The essence of a good dilemma lies on the heat-generating, pulsating effect it has, not only on the character, but also on the audience. If cinema equals point of view, and if the audience is destined to see, hear, and feel the same way our hero does, then, the dilemma must be the bridge in charge of connecting those emotions between both sides of the screen.

However, before a gut-wrenching dilemma is able to disarm the audience, the filmmaker has to be sure that the audience is feeling towards the character the exact emotion he wants them to be feeling by that point of the story: Empathy.

The audience might not like the character, but they must be rooting for him despite the morality of such character. For a dilemma to work, “The audience must want to get the treasure as much as the pirate does.”

At the beginning of The Bicycle Thief, we see a man, trying to make an honest living in post-war Italy. In an apparently jobless world, he gets one. He needs a bicycle or else he´ll lose this opportunity. He does not have one, but he is able to buy one by selling his bed linings. He is a loving husband, and even more so, a caring father, so, when his bicycle is stolen, it is no surprise that the audience desperately wants him to get it back.

During the entire journey to find the untraceable bicycle, he proves himself a moral man all the way in, always emanating an example of patience and virtue for his son.

In the final scene, when the character is all rundown and emotionally massacred by the circumstances, he finds himself in front of the dilemma of stealing someone else´s bicycle, and finally, he can easily put an end to this intoxicating day. By this moment, and I can bet one hundred dollars to anyone reading this, the audience is doing nothing but rooting for the honest man to do something dishonest. Why? Empathy.


3. All that Heaven Allows (Douglas Sir, 1955), Ali: Fear Eats The Soul (Rainer Weiner Fassbinder, 1974), Far from Heaven (Todd Haynes, 2002)

Far From Heaven

What it can teach you: Dilemma is mostly (not always, but mostly) determined by choosing between what is best for myself versus what is best for the greater good?

“No one can live without others, Emmi,” is the warning to the main character of the Rainer Werner Fassbinder film, Ali: Fear Eats The Soul, when she flirts with the idea of abandoning her solitary life, by taking up company with a Moroccan man named Ali. Why is it a warning when her actions seem to be in agreement with that statement? She just wants her empty life to be a little bit more bearable with the company of someone else. When Emmi, an old German cleaning lady, the pure image of melancholia and nostalgia, decides to marry Ali, a soft-spoken Moroccan immigrant living in post-Munich 1972, Berlin, her life flushes down into a spiral of misunderstanding, alienation, and racism.

Can you isolate yourself from the world, when you choose not to be lonely anymore?

This Douglas Sirk, Werner Fassbinder, Todd Haynes makeshift trilogy of films explores the rhetoric of this question, by questioning the subjects of happiness themselves. Through the eyes of lonely women trapped inside the twirling ironies of hypocritical societies, these three filmmakers try not to find an answer to the matters of rejection within society, but to deepen the illusion of the inquiry.

Jane Wyman, Brigitte Mira, and Julianne Moore play three very different while equally lonely women. All of them in love with men, different from themselves, in class, age, and race. Each one of them is unable to be happy with the man who makes her happy, because the people who surround her are unhappy to see her happy with a man with whom society says she should not be happy.

Is my happiness more important than the happiness of my “loved ones”? This same quiet dilemma carries the narrative of the three films with uproarious strength, and, demonstrates, how even the softest of characters, when faced with a dilemma that challenges his or her own conveniences, can possess the loudest presence.


4. The Godfather (Francis Ford Coppola, 1972)

The Godfather (1972)

What it can teach you: Dilemmas should always reveal the true nature of a character.

We all know the story of Michael Corleone, perhaps, the most recognizable anti-hero of cinema. His story, portrayed along a trilogy of crusades, is one of shredding poetry and cannibalistic personalities. What´s so interesting about this character and his story is its adaptability to any narrative context. It has all the treason elements to be a Greek tragedy, and all the dramatic twists to be a Shakespearean play.

It is, ultimately, the story of a prince who didn´t want to be king, but ended up inheriting the kingdom thanks to a series of dilemmas that forced him not only to choose between family and morality, but that coerced him to break free from any spoor of humanity, in order to be able to make those decisions.

The Godfather´s narrative adaptability comes from the potential to reveal the true nature of Michael Corleone, from the inherent evil that lives within him, to the tender instinct of protection that overpowers him, with pencil-sharp dilemmas whose only purpose are to challenge the hero step-by-step. The audience understands who this character is by the choices he is obliged to make, even if it means along the way, the expectations and hopes we had for this character when we first met him, as a war hero coming back home for his sister´s wedding, will shatter and crumble like rotten bones.


5. Kramer vs. Kramer (Robert Benton, 1979)


What it can teach you: Dilemma must show how much the character has changed.

A dilemma, rich in conflict, works in favor of the story, not only to integrate the chunks of a powerful narration sprinkled with unexpected twists. Besides always moving the story forward through character choice, a dilemma also serves a much simpler yet rather complex purpose. It demonstrates character change.

In Kramer vs. Kramer, when we first meet Ted Kramer (Dustin Hoffman), he is an egotistical father and a misogynistic husband, who worries more about a work-related phone call than listening to his wife expressing in hushed whimpers that she is leaving him for good. Once he gets stuck with the head over heels situation of the film (taking care of his six-year-old son, Billy, all by himself), he will undergo a series of situations that will transform him into a different kind of man, but how will the audience know he has really changed? And especially, when?

During his journey to become a good father, Ted learns how to make French toast, he reads bedtime stories to Billy, he loses his job, but he gets another one a day before Christmas, etc. When it seems he is getting the hang of it, his wife, Joanna (Meryl Streep), reappears, demanding the custody of Billy. Ted wants Billy for himself. He is mad at her. He is still selfish.

It all points Ted is going to lose custody, but his lawyer offers a final option: Billy must take the stand and decide, in front of the judge, his mother, his father, and a bunch of strangers, with whom he wants to live. Therefore, a final dilemma comes up for Ted. He can either take the risk of emotionally scarring his child by making him take the stand, and most likely win the custody, or he can avoid that kind of suffering for Billy, but lose him. “I won’t make him do that,”-Ted finally utters.

With this action, Ted endears himself to the audience, because they now know he is no longer the selfish human being we saw at the beginning. Only a blustery dilemma of this magnitude can make the audience aware of such character change.


6. Tootsie (Sydney Pollack, 1982)

Tootsie movie image Dustin Hoffman

What it can teach you: Dilemmas must incite a character to be selfish.

Every dilemma comes with moments of struggling meditation for the character, moments in which the hero needs to confront the facts and risks for each of the paths that have been set in front of him during this crossroads. If there is nothing the character can lose from the situation, then the dilemma is not really a dilemma and if there is nothing the character can win from a situation, well then the dilemma is not really a great dilemma.

The character needs to be a selfish prick for the most part of act two, so that in act three, he might be able to change, and fulfill his whole potential. The character must be aware of the consequences for each of the options he is capable to choose, and therefore select those that benefit him the most. Usually, these first selfish decisions, \ seem to carry immediate wins for him, but in retrospect end up pushing the character further and further away from what he really needs. It is the classic clashing of interests between what the character wants and what the character needs, but is unaware of needing.

In Tootsie, Dustin Hoffman plays Michael Dorsey, a misogynistic, unemployed actor whom nobody wants to hire. He is terrific. He is a pain in the ass. He is searching to finance his best friend´s play and to get his name back in the acting game. Given that he is unable to get a role as a man, he transforms himself into Dorothy Michaels, a middle-aged soap opera actress who becomes an instant star.

Every dilemma in this film evolves into a bigger dilemma of its own. It’s a stairway of difficult situations, built one after the other, thanks to the decisions the main character takes in order to keep his secret safe. From having sex with the friend he betrayed to get the role, to becoming the “fiancée” of an old widower man, each choice keeps him farther and farther away from the only woman he has ever loved.


7. Sophie’s Choice (Alan J. Pakula, 1982), Thelma and Louise (Ridley Scott, 1991)


What it can teach you: Immediate dilemmas must be gut-wrenching. They must show the journey of the character in a matter of seconds.

There are two kinds of dilemmas: those that stretch during the whole duration of the film and those that influence as fast as a bullet. The first kind (as we´ve seen with other entries on this list), break down into smaller conflicts that allow the second kind to blossom like spring flowers.

If you haven´t seen Sophie´s Choice or Thelma and Louise, all you need to know is that both films are about heroines so utterly ordinary on the outside that their uniqueness comes from them reacting to the in hospitality of this second kind of dilemma, immediate dilemmas.

Thelma and Louise embark on a high road journey, plagued with blue skies, red-blooded sunsets, and the toxicity of freedom poisoning the air around them. That is, until the catharsis of their actions, leads them to the end of the road, to an unforeseen momentum of doom. Sophie, on the other hand, while being locked in a house with cheap, flamingo walls, and embraces the stormy love of two very different men, is haunted by the memory of a decision she had to take, a choice from which she will never escape.

One tragedy ends, the other one begins, both with a moment of split-second choices.