< back

A Closer Look at “Sideways,” and How Dramatic Danger Holds the Key to Unlocking the Heart of Your Successful Screenplay

Countless movies break the so-called “rules of screenwriting,” proving that nothing trumps good storytelling.

The Departed's grim violence and bleak fatality fall far outside traditional norms of the "sellable" screenplay.

Here’s the true reality of the entertainment industry: good, heart-and-soul writing is what advances careers – it’s what gets writers representation, it’s what gets writers staffed on TV shows, it’s what lands development deals, it’s what gets scripts optioned and it’s what separates the mediocre forgettable movies from the modern classics. Hollywood is always hungry to find writers that will make for sound investments – and when someone comes around with a poised, self-assured, quality script, there is always a producer, agent and/or star running close behind hoping to capitalize on his talent.

Unfortunately, there’s so much contradicting screenwriting rhetoric out there that many writers end up scrambling into their heads trying to “get it right” – listening to others versus listening to themselves, seeking to satisfy the traditional formulas, trying to apply the various principles they’ve gleaned from the latest books and magazines, etc – and they end up drifting away from their inspired story idea toward a half-baked, tepid project that reads like every other scriptmaking the daily rounds. What starts as a product of creative passion so often becomes a source of confused frustration – and, worse yet, the author has compromised his shot at writing the kind of cohesively great script that demands industry attention.

I have devised a no-nonsense, practical approach to screenwriting that throws all the cluttered jargon out the window and instead unlocks the heart of the story that a writer’s passionate about telling. It’s an inside-out approach that helps writers: 1) succinctly identify their clear story idea 2) craft the highest-stakes story to effectively dramatize that idea 3) leave the audience satisfied with an organic conclusion that pays off the building journey. In essence, my accessible principles provide a strong foundation for smart, cohesive storytelling – the kind of storytelling that forces industry professionals to pay immediate attention.

The Path of Dangerous Recommitment

The key to unlocking the heart of any story lies in a hero’s willingness to take a particular value system, idea or goal from an initial conservative approach of minimal risk all the way to the end of the line to a place of impenetrable danger.

The more your hero undertakes a specific committed fight to a place of great peril, the more your movie comes alive with the kind of unstoppable dramatic momentum and clarity that makes for organically great storytelling:

  • Boogie Nights' Dirk Diggler (Mark Wahlberg) shows a poignant willingness to pursue his dream of being "Somebody" into reckless, self-destructive territory.

    Doesn’t a movie like Boogie Nights get its surprising pathos from Dirk Diggler’s willingness to pursue stardom through the destructive world of pornography and into the even more destructive worlds of drugs and petty crime? The movie’s surprising humanity comes from Dirk’s earnest resolution to be “Somebody” whatever the cost.

  • The righteous fire of a movie like Erin Brockovich stems from the titular heroine’s willingness to compromise her professional and private lives in order to stick up for the little guy – the compelling dramatic tension stems from her absolute refusal to back away from a case that ultimately threatens to let more people down than accomplish any good.
  • The sweeping tragedy of Brokeback Mountain come from cowboy Ennis Del Mar’s driving need to keep his emotional life compartmentalized at the expense of his family, his career and ultimately his one true love –the power of the understated final scene comes from the understanding that Ennis’ closed heart has condemned him to the bleak life of an isolated drifter.

These characters all possess a clear personal code that means the world to them and they’re all willing to steamroll these crusades into a place of maximum danger where they stand to lose everything. The more the world closes in on them demanding some sort of surrender, the more these heroes fight back with every last resource available no matter the possible cost: Dirk Diggler will live off his sexual prowess even if it means giving private shows to closeted johns in remote parking lots for a measly five bucks; Erin Brockovich will stick to her stubborn resolve even if it means neglecting her children and alienating the more knowledgeable professionals that could see the case through to completion; Ennis Del Mar will remain shut down even it means hurting those he loves the most.

This means we have a dynamic flow of new information from beginning to end of the movie: the hero’s every step forward into exciting, uncharted territory actually puts him in more perilous waters than ever before. We’re simultaneously thrilled by the hero’s tenacious ability to keep his crusade going regardless of the risk and also filled with anticipation over his impending day of reckoning where his way of life simply will not work anymore. Even better, every single moment springs entirely from the hero’s specific, committed will – creating the kind of effortless dramatic unity that makes for a truly meaningful movie experience.

This is the most difficult task facing a screenwriter – taking an intellectual “theme” or “premise” and making it come alive on the screen. And yet it all boils down to basic common sense: a thematic value on its own is just an idea – flat, cerebral, two-dimensional – it takes an active hero to give an idea actual life and motion. The more fully a hero embodies a certain value system or philosophy, the more a movie’s central theme pops off the screen through specific dramatic action. The hero’s willingness to steamroll this crusade into the most dangerous territory possible allows us to see the idea’s full range of motion, to see the limits of its existence, to see the true extent of its durability and power. Only when a hero has fought to the bitter end, only when a hero has burned through every available option and resource, can a movie at last come to a meaningful conclusion about its central idea.

Consider something like the 2005 sleeper smash Sideways: have you ever stopped to wonder just how screenwriters Alexander Payne and Jim Taylor managed to make an aggressively bleak, talking-head movie about an unapologetically self-obsessed alcoholic that went on to earn over 70 million dollars at the box office? Have you ever considered just how Payne and Taylor got away with breaking all manner of Hollywood notions of “what sells” and still had audiences buzzing with excitement? Let’s take a closer look at Sideways to see how the strength of Miles’ heroic conviction holds it all together.

Paul Giamatti engages the viewer with his diehard commitment to a destructive crusade

The Conservative Approach

Doesn’t the immediate acerbic thrill ofSideways come from the lengths Miles is willing to go to stay stuck in self-victimizing misery? In the first few minutes alone, we see Miles recovering from an alcoholic hangover, running late as a result of his hangover, compulsively lying to cover for his lateness, passive-aggressively running still later, spinning still more lies to cover for his continued lateness and throwing a temper tantrum when he doesn’t get his way. Even more outrageous, Miles uses snooty perfectionism to justify his reckless dysfunction: his refined sense of wine masks his actual alcoholism, his refined sense of romance masks his inability to let go of his previous marriage, his refined literary sensibility mask his inability to complete his perpetually unfinished novel.

By the end of these opening sequences, we not only understand what matters most to Miles but also how he has managed to build an entire existence around this value system: how he perpetuates it, how he justifies it, how he gets away with it, how it shows up in every facet of his life ranging from the big issues to the most trivial details of daily existence. There’s not a single digressive or vague beat in Sideways’entire first act: Miles’ clearly defined crusade powers every scene forward, and it is the precisely the clarity, specificity and breadth of his dramatic conviction that gets this otherwise understated movie going on all four cylinders. Sideways definitively proves that we don’t need conventionally likable characters or contrived dramatic fireworks to create a powerhouse opening – all we need is a clearly defined hero committed to a clearly defined cause.

Blowing the Crusade Up to Dangerous New Dimension

Payne and Alexander then bring Miles’ carefully constructed stagnancy under immediate crisis: his deified ex-wife has decided to remarry, his enabling best friend Jack (Thomas Hayden Church) has resolved to settle down into his fiancée’s family business and, most importantly, beautiful fellow wine aficionado Maya (Virginia Madsen) shows improbable romantic interest in him. Rather than surrender to the obvious tides of life change, Miles instead digs his melodramatic heels into the ground and sabotages this shot at a redemptive new beginning by pursuing Maya under false pretenses including the outright lie that his book has been signed for imminent publication.

Giamatti takes his crusade to new heights of danger when he risks his shot at true love

Essentially, then, Miles has steamrolled his initial conservative crusade into new high-risk dimension: Miles is no longer spinning casual lies to mere acquaintances and friends, he’s outright deceiving the woman he loves; he’s no longer sabotaging a life barely worth noting, he’s sabotaging an unexpected shot at a truly rewarding existence; he’s no longer paying mere affected tribute to a refined lifestyle, he’s on the precipice of a new world that actually embodies his deepest passions.

The more the movie charges forward, the more Miles runs his crusade into the ground regardless of the possible consequences: Miles’ initial functional alcoholism morphs into creating a drunken spectacle at an upscale wine bar (Miles defiantly throws a jug of spit-out wine over his own head); Miles’ passively enabling his best friend’s infidelity morphs into literally crashing his own car as a means of helping the cheater create a credible cover story; Miles initial angst over his novel turns into complete and utter publisher rejection. In essence, Sideways builds its dramatic momentum from Miles’ willingness to push his clearly defined crusade into harrowingly pathetic dramatic territory that threatens to undo him for good.

The End of the Line

Miles takes his scrupulousness so far that he ultimately finds himself painted in a corner where his old way of life simply will not work anymore: he alienates Maya, he loses his last possible chance at a book deal and he very nearly suffers bodily harm as a result of his best friend’s similarly self-destructive streak. Miles effectively burns through his every last narcissistic resource until he reaches such a severe dead end that he has no choice but to finally step outside of his usual victimization and take some measure of responsibility for how pathetic his life has become.

Giamatti gets to the end of the line where he must finally confront the truth he hoped to avoid

Miles’ resolution to take his crusade to the absolute end of the line is the very thing that ultimately forces him to open his eyes to some hard truths – and thereby allows Sideways to make a succinct concluding point about the necessity of personal accountability in stepping into a life that matches your innate talents. If Miles were not consumed with his self-obsessed histrionics to the exclusion of all else, then he would never reach this place of dire consequence where he must finally choose whether to keep running his life into the ground or finally make a new choice. The sheer force of heroic will established at the beginning of the movie is the very thing that brings about Miles’ inevitable day of reckoning – and Sideways therefore hangs together with the kind of dramatic unity that cannot be arrived at by intellectual calculation or paradigm storytelling.

Bringing It All Together

Sideways provides just one example of how the path of dangerous recommitment can bring even the most challenging story to high-stakes, dynamic life. Take a look at just about any classic screenplay and you’ll find this powerful principle holding it together regardless of genre, setting or time period:

Thelma & Louise

Thelma and Louise (Geena Davis, Susan Sarandon) fight for their personal freedom from beginning to end of the movie: they start out impulsively fleeing their unhappy relationships on a weekend getaway, they then impulsively flee the law for a new life in Mexico and they finally impulsively flee into the Grand Canyon rather than compromise their newfound sense of liberation. Thelma and Louise gets it triumphant spirit from the heroines’ willingness to steamroll their freedom crusade from fugitive weekend to fugitive outlaws to fugitive suicide run – and their final descent represents the most high-stakes, dangerous version of the personal stand established in Act I.

In the Bedroom

Antihero Ruth Fowler (Sissy Spacek) fights for punishing vengeance from beginning to end of the movie: she starts out micromanaging her son’s life as a passive-aggressive way of punishing her family for not having been allowed to conceive more children like she had originally wanted, she then plays the martyr over her son’s shocking death as way of punishing her husband for now being childless, and she finally convinces her husband to kill their son’s murderer as a passive-aggressive means of avenging her life’s perceived injustices. In the Bedroom gets its haunting eeriness from Ruth’s willingness to pursue her angry crusade from vengeful motherto vengeful martyr to vengeful killer – and her final quietly lethal act represents the highest-stakes, most dangerous version of the punishing bossiness established in Act I.

The Lord of the Rings: The Fellowship of the Ring

Young hobbit Frodo (Elijah Wood) fights to fulfill his duty to the larger good from beginning to end of the movie: he starts out transporting the destructive Ring out of the Shire as a means of saving his community from inevitable destruction, he then forms a fellowship to bring the ring to the site of its creation as a means of saving the fate of the entire world, and he finally steps into his destined but deadly role as the sole ring bearer in order to see the mission through to completion. The Lord of the Rings gets is moving humanity from Frodo’s willingness to steamroll his altruistic crusade fromcommunity duty to global duty to cosmic duty – and his final brave act of selflessness represents the highest-stakes, most dangerous version of the humble duty established in Act I.

The path of dangerous recommitment proves to be such an immensely powerful principle because it guarantees a rushing tide of new dramatic information: whetherAmerican Beauty’s Lester (Kevin Spacey) takes his defiant rejuvenation to a place of inappropriate sexual conquest or The Departed’s undercover agent Billy Costigan (Leonardo Dicaprio) takes his split identity to a realm where he becomes targeted by both the cops and the criminals, the truly effective film hero thrills us by undertaking a journey that actually goes somewhere, that continually pushes the limits of his existence into heightened new territory, that forgoes repetitive circles in favor of progressively high stakes. These heroes all take a bold jump into the deep abyss – and because they remain wholly committed to a specific set of convictions, every moment of the movie hangs together with total thematic unity.

This manifesto will walk writers through the principles I use with my clients to create a solid path of dangerous recommitment:

How to Define Your Hero’s Crusade: What set of convictions does your hero fight for from beginning to end of the movie? What is at stake for your hero on a personal/emotional level? What ideal or belief powers your hero’s every movement forward?

How to Create Your Hero’s Conservative Approach: How does your hero dynamically embody these values from the very beginning of the movie? How do these values show up in your hero’s everyday life?

How to Bring Your Hero’s Under Immediate Crisis: What level of conflict has put your hero’s life in jeopardy? What obstacles force your hero to fight back with dangerous recommitment?

How to Create a Path of Dangerous Recommitment: How does your hero dangerously recommit to his crusade? How does your hero blow up his initial crusade into a place of thrilling, do-or-die dimension?

How to Get to the End of the Line: How does your hero reach the most dangerous version of his initial crusade? How does his way of life simply not work anymore? What sort of dramatic impasse does he reach?

How to Make a Cohesive Concluding Statement: How does your hero deal with the end of the line? Does he learn to amend his ways? Or does he go for broke and run his life into the ground? What does your movie want to say about your hero’s chief conviction? What point are you making about the world of your story?

Comments are closed.