The Expanded Ultimate Story Checklist: Does the concept contain an intriguing ironic contradiction?

So I’ve promised you many different types of irony, and now I’m ready to deliver the first two, ironic concept and ironic title. Let’s look at the ironies contained in those same example stories: 

• Casablanca: The least patriotic American has to save the Allied cause. 
• Beloved: A mother kills her daughter to ensure her freedom. 
• Silence of the Lambs: The only way to catch one serial killer is to work with another serial killer. 
• Groundhog Day: A man who just wants to get his least favorite day over with has to live it again and again. 
• Harry Potter and the Philosopher’s Stone: A miserable and unfortunate kid discovers that he’s secretly rich, famous, and heroic. 
• Sideways: A man helps his friend celebrate his upcoming wedding by playing wingman for him as he pursues other women. 
• Iron Man: An arms dealer is attacked with his own weapons and then declares war on arms dealing. 
• An Education: A girl rejects the idea of getting “an education” but learns another meaning of the word in the process. 

Because this rule is so nearly universal, it’s instructive to look at an exception that proves the rule. A few years ago, Denzel Washington directed and starred in a highly fictionalized true story called The Great Debaters about a debate team at an all-black college that gets to challenge the Harvard team in the 1930s. As it happens, the team gets assigned to defend the proposition that civil disobedience is good. They do a good job with that and win, which is good, because otherwise what would the movie be saying?

This movie is actually worth watching, but it commits the cardinal sin of many well-meaning period pieces: It irons out the irony.

What makes this so frustrating is there is a lot of potential irony inherent in the premise, if the makers of the film had been willing to fictionalize it a little bit more. Here’s why college debate teams are interesting: You don’t get to choose which side you argue—it is randomly assigned. So what if the black team had been assigned the anti-civil rights side of the argument?

The team would balk, but then, after a few stern speeches from Washington, they would realize this was their big opportunity. They would have to create devastating anti-integration arguments, but the more they proved that blacks weren’t equal in theory, the more their eloquence would prove they were equal in reality!

At that point you could end the movie either way and it would still be powerfully ironic. With that ending in doubt, the whole movie would come alive. Instead, with the version they made, we know the whole time that there’s only one way to end it, unless they want to make it look like integration was a big mistake.

Of course, another problem is that The Great Debaters is a terrible title. You can tell right away it has no irony. It always drives me crazy when I see a fantasy novel with a title like The Knight’s Sword or an airport paperback with a title like Deadly Assassin. These titles are telling you right off the bat that this book will be predictable. A good story needs conflict, and why not start with the title, which is your first opportunity to set two incongruous elements against each other?

Just glancing down the list of underrated movies I’ve recommended on my blog over the years, I see that these titles are inherently intriguing: Blast of Silence, Dark Days, Killer’s Kiss, The Little Fugitive, Little Murders, My Favorite Wife, Safety Last, Unfaithfully Yours, and The White Sheik.

The Court Jester, on the other hand, is a great movie, but it has an inherently weak title, because where else would a jester be? Shoot to Kill could be the title of any thriller ever made. And Fritz Lang rightly complained when the studio changed the name of his movie from the ironic The Human Beast to Human Desire. Lang demanded to know, “What other kind of desire is there?” An ironic concept is great, and an ironic title is a nice bonus on top of that.

The 40 Year Old Virgin	YES. A handsome 40 year old man is a virgin.
Alien	Sort of: answer a distress signal, almost all of them get killed as a result.
An Education	YES. She wants an education, but doesn’t realize which kind she’ll get. The glamorous sophisticates are lowly crooks.
The Babadook	YES. A son must fear his mother.  A hunt for external monsters leads to the discover of an internal monster.
Blazing Saddles	YES. Very much so: A black must save a town of rasists in order to save himself (and empower his people).
Blue Velvet	YES. An idealistic amateur detective discovers he’s just as creepy as those he investigates.
The Bourne Identity	YES. A spy with a conscience becomes the latest target of his own agency.
Bridesmaids	YES. The bridesmaids are not maidenly. An attempt to plan a happy celebration becomes a nasty conflict.
Casablanca	YES. The least patriotic American has to save the Allied cause.
Chinatown	YES. The ultimate cynic finds out he’s actually naïve.
Donnie Brasco	YES.  an undercover FBI agent finds his pitiful targets more sympathetic than his bosses.
Do the Right Thing	YES. A comedy about a race riot.
The Farewell	YES. Lying for an honorable reason, withholding aggressive medical care with the idea that it would do more harm than good because of the fear it would cause
The Fighter	YES. Sort of: a gentle boxer lacks self-esteem.
Frozen	YES. Having to stop (and maybe kill) the person you most love.
The Fugitive	YES. A wealthy doctor learns what it’s like to be a dehumanized convict, and a marshall realizes that he himself can sometimes be the bad guy.
Get Out	YES. These liberals love black people a little bit too much.
Groundhog Day	YES. A man who just wants to get his least favorite day over has to live it again and again..
How to Train Your Dragon	YES. A dragon killer in training succeeds by befriending a dragon.
In a Lonely Place	YES. a writer of crime stories is caught up in one.
Iron Man	YES. Many: He thinks his products are making everyone free, but they’re in the hands of his evil captors. He has an impervious shell but a weak heart. An arms merchant wants to disarm the world.
Lady Bird	Not really.  The cover image is very slightly incongruous: a girl with colored hair at a catholic school, but that doesn’t really rise to the level of irony.
Raising Arizona	YES. Hi tries to goes straight by kidnapping a baby.
Rushmore	YES. Somewhat: a young man who acts old.
Selma	YES. A non-violent army.  The most powerless people in the country bending the most powerful man in the country to their well.  The only way they can win is to find a violent sheriff who’s willing to beat them up.
The Shining	Somewhat: the family becomes a source of danger, when the world goes crazy only the crazy kid seems sane...
Sideways	YES. Not really for Miles, but yes for Jack, a man looking for love on the eve of his wedding.
The Silence of the Lambs	YES. The only way to catch one serial killer is to work with another.
Star Wars	YES. The kid who didn’t get to go join the rebellion becomes the hero of the rebellion.
Sunset Boulevard	YES. The nation’s most glamorous people are deluded lowlifes, etc.