NOTE: The following is a revised version of an article originally published on Medium, where I’ve published a number of writing advice pieces.

Warning: Contains spoilers for Born on the Fourth of July, Rain Man, Schindler’s List, Indiana Jones and the Last Crusade, Treasure Island, Five on a Treasure Island, Moonfleet, The Treasure of the Sierra Madre, Breaking Bad, The Witch, The Wizard of Oz, Romeo and Juliet, The Catcher in the Rye, Macbeth, and The Hitch Hiker’s Guide to the Galaxy.

Alanis Morissette famously complained that rain on a wedding day was ironic, when in fact that was just bad luck. However, she isn’t alone in her confusion regarding the nature of irony. Despite the standard definitions of verbal, situational, and dramatic irony, it’s a tricky concept to explain, and even trickier to consciously nail in fiction (some of the ironies in my own novels have been happy accidents). However, ironic stories are extremely satisfying to read or watch when the concept is properly understood.

One method of crafting an ironic story is to create a central protagonist with a convincingly ironic character arc. For the best results, I recommend first figuring out where you want your character to end up, and working backward from that point, weaving irony into the narrative. For example, a rich man systematically bankrupts himself to save lives. What ironic events would bring him to that point? I’ll come back to this question in a moment.

Ironic character arcs are best defined in two ways: Firstly, by what they aren’t, and secondly, because irony is by nature slippery and difficult to define, with examples. Irony isn’t sarcasm, bad luck, coincidence, or ambiguity, as some have claimed. A sarcastic character isn’t ironic for that reason. Simple bad luck or coincidence does not provide the deep rush of profound insight inherent in an ironic story. There is nothing ambiguous about irony either. Ironic character arcs communicate a crystal-clear truth to the reader or viewer, leaving them in no doubt. Furthermore, they typically come in two forms: redemptive and punitive.

Redemptive ironic character arcs

Redemptive ironic character arcs can be roughly defined this way: The protagonist pursues goals initially esteemed and greatly valued, perhaps obsessively. These goals can be financial, career, or love life-related. They can be politically, socially, or spiritually motivated. However, the compulsion to realise these goals drives the protagonist to the verge of despair and self-destruction.

Any intelligent audience is aware of the character flaws that drive the protagonist on their obsessive quest because they have the self-awareness and objectivity the protagonist lacks. However, in the redemptive ironic character arc, the protagonist eventually experiences an epiphany that brings about profound change, wherein they have a moment of clarity, look at themselves in the mirror, disregard their original goals, and achieve something far greater.

Films like Born on the Fourth of July, Rain Man, and Schindler’s List are good examples of this storytelling principle. Ron Kovic begins Born on the Fourth of July as a gung-ho Vietnam War recruit but is wounded in combat and paralysed from the mid-chest down. He returns home, still driven by patriotic fervour, but gradually changes his views as he degenerates into political disillusionment, self-pity, and rage. Eventually, after PTSD moves him to confess to a friendly fire incident, Kovic emerges as an anti-war activist; a role ironically requiring the same courage he displayed on the battlefield, as protestors clash with riot police.

Tom Cruise is excellent as Kovic and equally excellent as Charlie Babbit in Rain Man, where he plays a ruthless, selfish car dealer. Following the death of his estranged father, Charlie is furious to discover his inheritance goes to his autistic brother Raymond; a brother he never knew he had. Charlie in effect kidnaps Raymond and takes him on a road trip, hoping to leverage a deal with the lawyers so he’ll get a chunk of the inheritance. But as time passes, Charlie bonds with his long-lost brother, and by the time the lawyers are ready to make a deal, he no longer wants to be parted from him. The money ceases to matter to him. He wants the relationship with his brother instead.

Schindler’s List features another redemptive ironic character arc, one alluded to in my introduction: A rich man systematically bankrupts himself to save lives. What ironic events would bring him to that point? Oscar Schindler was a member of the Nazi party and a profiteer of slave labor, yet a crisis of conscience at the treatment of the Jews in wartime Poland caused him to systematically bankrupt himself to save as many lives as he could. His original goals are sacrificed in favor of a greater moral imperative, giving him a redemptive ironic character arc.

Treasure hunt narratives

Another good example of the redemptive ironic character arc is often found in treasure hunt stories. The protagonist obsessively searches for treasure, yet ultimately the greatest treasure is not the object of the quest, but something else more important gained along the way. The treasure turns out to be a side benefit to a greater reward ultimately received by the protagonist, or in some cases, the protagonist does not retain the treasure at all.

In Indiana Jones and the Last Crusade, Henry Jones Sr spends his life in an obsessive pursuit of the Holy Grail. For forty years he meticulously chronicles endless clues, to the exclusion of all else, including his son. As a result, Indy is estranged from his father for years. But when the Nazis attempt to uncover the Grail and Henry is kidnapped, Indy rescues him. They try to find the Grail before the Nazis, and in the process, both gain something far greater: The restoration of their relationship.

Other famous treasure hunt stories follow this pattern, including Robert Louis Stevenson’s Treasure Island, probably the most famous treasure hunt story of all time. Jim is excited by his quest, but his relationships with the other colourful characters, especially Long John Silver, are what drives his character arc. Yes, the heroes ultimately keep the pirate treasure, but Jim’s rite of passage to manhood is the more interesting aspect of the tale, and his experiences are his greatest gain.

Another example is Enid Blyton’s Five on a Treasure Island. It features a treasure discovering narrative that rescues George’s parents from pseudo-middle-class poverty, so they can send George to a posh private school. This rather laughable call on reader sympathy and its subsequent resolution is not the most satisfying upshot for George and the other children. Instead, George’s character arc from an angry, distrustful loner to someone with close friends is the ultimate reward for her endeavours.

Punitive ironic character arcs

By contrast, punitive ironic character arcs often involve falls from grace. For example, sticking with treasure hunt narratives, an inverted principle comes into play when such tales have a darker, more tragic side, especially when characters become unduly obsessed with the treasure they seek. Fred Dobbs in The Treasure of the Sierra Madre or Elzevir in Moonfleet are good examples. It can be equally satisfying to see these characters obtain the treasure (often temporarily) whilst losing everything that actually matters.

The punitive ironic character arc can be roughly defined this way: The protagonist pursues what they believe is a noble goal through dubious means, unaware of their own flaws and hypocrisy. They increasingly believe their self-justification and lies, and this lack of self-awareness makes them vulnerable to the very kinds of behaviour and action they condemn.

Again, these stories can centre around financial gain, career, love life, politics, criminality, religion, and so forth. At a critical point, the protagonist reaches a similar crisis that mirrors that in the redemptive ironic arc, only this time rather than pull back from the abyss, they tip over the edge, committing acts that directly contradict the very values they profess.

Shakespeare’s Macbeth is an obvious example. Macbeth’s actions are set in motion as a result of his consultation with the witches. Had he disregarded their prophecies, his ambitions and desires would have been fulfilled in any case, since King Duncan already favoured him, naming him Thane of Cawdor and heir to the throne. Instead, the famous bloody tragedy ensues.

Television series Breaking Bad is another excellent case in point. Walter White’s descent into evil is bone-chilling and darkly funny. A law-abiding citizen fatally flawed by pride, Walter starts secretly manufacturing crystal meth to pay medical bills and provide for his family after a cancer diagnosis. However, the audience recognizes something Walter takes five series to admit: he’s doing this for his own gratification. Walter gradually deteriorates into full-blown megalomania, allowing for a rich vein of irony in his character arc as hospital bills become irrelevant, and he loses the family he originally wanted to support.

Horror film The Witch provides another fascinating example of punitive irony. A family of Puritan settlers too uptight for regular Puritans believes they are being targeted by a witch in the forest. The father is completely obsessed with the idea of sin, and forces strict religious ideology on his charges, especially his teenage daughter, who he comes to believe is a witch. As the hysteria escalates, the daughter, who had no intention of becoming a witch, ends up becoming a witch, demonstrating the ironic truth that the more religious people are obsessed with their ideas of sinfulness, the more likely they are to manifest it. One only has to look at the various scandals in the church for evidence.

Conclusion: Irony adds value

In conclusion, embracing irony in fiction is difficult but worthwhile, especially when writing a protagonist with an ironic character arc. You will probably find multiple methods to organically evolve ironic themes as you plan the narrative, and even more, in the writing process itself. For example irony in the plotting, will make any story sparkle. The fearsome wizard in The Wizard of Oz turning out to be a fraud is a superb ironic plot turn. The tragic irony at the end of Romeo and Juliet, where Romeo commits suicide thinking Juliet is already dead, is another powerful example.

At the very least, irony can add humour. Just look at Holden Caufield’s flippant attitude to the tumour in his brain in The Catcher in the Rye. Or the ridiculous intergalactic bureaucracy in The Hitch Hiker’s Guide to the Galaxy, wherein Arthur Dent protests that his house is due to be destroyed to make way for a bypass. He is greeted with bureaucratic indifference by the construction foreman: “The plans have been on display in the council for over a year. It’s not my fault you don’t take an interest in civic affairs.” Shortly afterward, Earth discovers it is to be destroyed by the Vogons to make way from an intergalactic bypass. The Vogon Commander states the plans have been on display at Alpha Centauri for over a year, and it isn’t his fault if humans don’t take an interest in civic affairs.

On that amusing note, as you write, may the irony be ever in your favour.