Don’t worry. Scriptshadow has the best outlining method in the business. Even the Outline Haterz are going to love it.

We are in WEEK 4 of our Writing 2 Scripts in 2024 Challenge. It is probably the most controversial week because this week we’re outlining. And, as we all know, there is a contingent of screenwriters who believe that outlining is Satan reincarnated. I’m not here to argue with those people. All I’m here to say is that the more prepared you are, the better your script tends to end up.

Here are the links to the first three Writing A Script posts if you need to catch up:

Week 1 – Concept
Week 2 – Solidifying Your Concept
Week 3 – Building Your Characters

As far as how much time I need from you this week, at the bare minimum, you need to give me an hour a day. But if you want your outline to have real impact, two hours is preferable. And for those of you youngsters who don’t have jobs yet and have all day to write, put in as much time as you’ve got because when it comes to writing a screenplay, your progress will be proportional to your preparation.

The idea here is we want to create CHECKPOINTS. These are key moments in the script where the scenes are of elevated importance. If you can construct a series of script checkpoints, you’ll always have something to write towards.

The more checkpoints you create, the shorter the distance until the next checkpoint, which makes writing easier. For example, if you have a checkpoint on page 10 and then your next checkpoint isn’t until page 50, that’s where you’re going to run into trouble. The amount of space feels too vast, you don’t know how to fill it up, which leads to the dreaded “writer’s block.”

Remember, writer’s block is rarely about your inability to come up with something to write. It’s more about a lack of planning. The more you plan, the more pieces of your screenplay will be in place, and the easier it will be to connect those dots together.

So here’s the first thing I want you to do. I want you to think of three big set-piece scenes. These are the scenes that are going to sell your screenplay. When you came up with your concept, these are often the first scenes you thought of. For example, if we were writing Barbie, a set piece scene would be the big “I’m Just Ken” musical number. In Heat, it’s that iconic bank robbery scene. In Spider-Man: No Way Home, it’s Dr. Octopus attacking Peter Parker on the highway. In Bridesmaids, it’s the dress try-on scene.

And don’t limit yourself to 3 if you want more. What was so cool about Fincher’s The Killer was every single scene was a set-piece. So he had like eight of them in there. Whatever’s right for your movie, come up with that number of set pieces. And if you really want to do this justice, come up with 20 set-piece ideas and whittle it down to the top 3.

Pro Tip: One of the easiest ways to separate yourself from the competition is to NOT SETTLE. If you settle for the first three ideas that come to you, your script is not going to be as good as if you came up with 20 ideas and picked the best three.

From there, open your outline document and place the scenes at the rough page number where you think they’ll work. Just post “Page 45 – I’m Just Ken musical number.” It doesn’t have to be perfect. Again, you just want to create these checkpoints that you’ll be able to move towards. Even if you only create these three checkpoints, you’ll be in better shape than if you went into your script naked.

The next thing I want you to figure out is your first scene. Your first scene is SO IMPORTANT. I could write 5000 words on the importance of the first scene and it wouldn’t be enough to convey just how important that scene is. So just trust me on that.

If I were you, I would not go with a “setup scene” as your opening scene. This is a scene where you’re setting up a character or setting up your plot. You know the opening scene of Die Hard? Where we meet John McClane on a plane? That’s a setup scene. You CAN do that if you really want. But it’s better to start with a dramatic scene that pulls the reader in.

My favorite example of this is Source Code – the spec script not the movie – A dude lands inside someone’s body on a train and is told he has eight minutes to find a bomb or the train blows up. But a more recent, less intense, example is Tuesday’s script I reviewed – The Getaway. A married couple attempts to have sex in an airplane bathroom and get busted for it. Just make something happen in that opening scene. Don’t bore us.

Okay, now we’re going to get into the technical stuff. Most writers don’t like to do these story beats because it’s, well, technical. Screenwriting is supposed to be free-flowing, fun, artistic. It’s art! Art should never be dictated by technicalities! Yeah, keep telling yourself that.

Screenwriting is inherently mathematical. It’s 110 pages. Those pages are divided into four sections – Act 1, Act 2.1, Act 2.2, Act 3. Essentially, each of those sections are going to be 27 pages long, although that will change depending on the length of your script. But the key to remember is that the end of each section will ALSO work as a checkpoint, since a major moment will happen at the end of each section.

Don’t worry. You’re not going to stick to this like a bible. The nature of writing is that you’re constantly generating new details in your story and those details will generate new story ideas. So, much of this is going to change. But we have to start somewhere.

Which leads us to the inciting incident. This is the thing that happens that INTERRUPTS your hero’s world, usually between pages 10-15. You know that moment in body-switch movies where they first switch bodies? That’s an inciting incident – it’s the disruption of your hero’s everyday existence that now forces them to act. In The Killer, it’s when our main character killer tries to assassinate his target but misses.

After this happens, your hero will be in denial. That’s because just like you and me, movie characters don’t like it when they’re forced to change. So they resist, resist, and resist. But then, at the end of Act 1, which will be your next checkpoint, they accept that they need to solve this problem and head off on their journey (usually around page 25).

The next checkpoint I want you to figure out is your midpoint (around pages 50-60). Now, midpoints are one of the trickier parts of a screenplay because every screenplay is so different that by the time you get to the midpoint, there is no “one-size-fits-all” scene you can write, like the inciting incident. Oppenheimer’s midpoint doesn’t have anything in common with Star Wars’s midpoint. The two movies are trying to do something completely different with their stories.

But something you can keep in mind is that you don’t want the second half of your movie to feel exactly like the first half of your movie. So, for example, if you’re writing a contained thriller where our heroine is being held captive in a basement that she’s trying to escape from – if you just have her try to escape for 90 straight minutes, we’re going to get bored. You need something to happen at the midpoint that changes the story up considerably.

Maybe the most obvious example of this is the movie, Room. The first half of that movie is a woman and her kid being held captive in a room. The midpoint is their big escape. And they succeed. The second half of the movie covers the aftermath as our heroine tries to deal with the trauma of what happened. You can’t do this with most movies. But it’s a great example of how the midpoint should affect the second half of your story.

A more subdued version would be The Equalizer 3. The first half is Robert McCall recuperating in this small Italian town, watching as a local gang makes the locals’ lives a living hell. He doesn’t do anything because, if he does, it will bring attention to himself. But at the midpoint, the gang goes too far, and Robert has had enough. So he starts taking them out one by one.

That’s a good example of a midpoint by the way. The midpoint should always make the second half BETTER, if possible. That’s why Room was not the perfect movie. Its first half was more entertaining than its second half. You always want it to be the opposite.

Once you have your midpoint, your next checkpoint will be the end of your second act (between pages 75 and 90). This is when your hero will “die,” – figuratively of course, but sometimes literally (The Princess Bride). They’ll be at their lowest point. They’ll have tried to solve the problem but failed. There are no other options. The audience should truly feel, in this moment, like there is NO WAY our hero can win. That’s when you know you’ve written a great finale to your second act. In Barbie, this is when Barbie comes back to Barbie Land only to realize that the Kens have taken over.

And the final major checkpoint is your climax. This should be easy because, if you set up a clear goal for your hero at the beginning of your story (John McClane – take down the terrorists and save my wife), then this is the scene where they’ll attempt to do that.

Also, the reason we did that character work last week is so that you can match up your character’s transformation with your climax. For example, if your character’s flaw is that they are selfish, your climax should test that selfishness. It should give them an opportunity to become selfless. If you can pull this transformation moment off, it’s the kind of thing that makes your script feel really intelligent and satisfying.

Okay, those are your major checkpoints. If you get all of those down, you should be in a really good place by the time you write “FADE IN.” However, if you want to go deeper, I prefer that you never go more than 12-15 pages without a checkpoint in your outline (12 if your script is 100 pages, 15 if it’s 120 pages). Even if you just have a cool idea for a scene – that’s all you need for a checkpoint. What we want to do here is close the gap between those big empty holes of space in your script so that you’re never writing in a void. That big void of empty space between checkpoints is when you start freaking out and get writer’s block.

Easy, right?

As you can see, I’m not big on these super-detailed outlines that include things like, “The Circular Resistance Modifier To The Protagonist’s Conflict Moment.” Screenplays are too varied for those specific moments to work in every script. My outlining method keeps things loose enough that you don’t feel controlled by your outline, but it’s tight enough that you have confidence when you start writing your script.

If you have any outlining questions, I’ll be dipping in and out of the comments all weekend. If I have time, I’ll answer what I can. Now start outlining! Cause next week, WE BEGIN WRITING!

The deadline for January Logline Showdown is THIS THURSDAY at 10pm! So if you have a logline you want to enter, follow this link and it will give you instructions on how to submit. This is the first Logline Showdown of the year so it’s a big one. Best five loglines will be posted Friday for the weekend competition.

Genre: Horror
Premise: A dysfunctional family’s weekend is interrupted when a strange man shows up at their door claiming to know the wife from many years ago.
About: Christopher Landon is one of the biggest horror directors in town. He was unfortunately part of that Scream 7 disaster where the entire movie imploded within seven days (lead actress getting canceled, the industry’s hottest young actress, Jenna Ortega, not counting Sydney Sweeney, also dropping out). Maybe there’s a movie idea there. A horror movie is a week away from shooting and the actors start getting killed one by one. Somebody write it. Anyway, Landon quickly moved onto this project which is none other than a… SHORT STORY! So, once again, we’ve got a big short story sale. If you’ve got Amazon Prime, you can read “Big Bad” for free over on their site.
Writer: Chandler Baker
Details: 62 pages

Yes, I know this is a site about screenplays thank you very much. But how can you expect me to ignore the hottest trend in story sales: SHORT STORIES. I just go where the money is, baby. And, as I’ve mentioned before, short stories aren’t that different than screenplays. In fact, today’s story is probably the same number of words as a 90 page screenplay. You’re just telling the story in a more descriptive medium.

Also, it’s been a long time since we’ve had a great werewolf movie. There was that one awesome werewolf script from last year. But I’m still looking for a werewolf movie that gave me the same feels as when I first saw The Lost Boys. Can Big Bad give me that oh-so-good feeling I’ve been waiting for? Time to bust out the dog treats and find out!

Sam and Rachel are the unhappy parents of girls Odie and June. The family lives in Eugene, Oregon and, right from the start, we sense this is a majorly dysfunctional crew. Rachel is a renowned academic with a good professorial job but her job is the only thing good in her life.

Sam was also once a renowned academic – that’s how they met – but these days he’s more of a recluse who writes in spits and spurts. We’re not sure why yet. But after switching POVs from Rachel to Sam, we learn that Sam despises something deep within his wife, something that, it appears, has infected their marriage since the beginning.

The town is dealing with a recent problem – landslides from the nearby mountains have taken down some of the town’s infrastructure. This has brought more animals into the area. And the predators have followed. The main predators that everyone is worried about are wolves.

A sick Rachel comes home from work and immediately starts arguing with Sam. The daughters watch. Sam sends them to bed. Then Sam takes Rachel downstairs into the basement. He comes back up without her. But before Sam can go to bed, there’s a knock on the door. It’s some guy claiming to be an old friend of Rachel’s. He wants to see her. Sam tells the guy to beat it but it takes a while to send him away.

Sam senses something is off, heads downstairs, and that’s when we realize Rachel is a werewolf. This is where she’s chained down when she turns. But the chains have been shed and there’s no sign of Rachel. This is VERY BAD NEWS. Sam hurries upstairs, ushers the girls into the attic, and goes down to find Rachel.

Instead, he finds the man from earlier, who reveals his true purpose for being here. He’s a werewolf hunter. And he’s not leaving until Rachel is dead. Heck, Sam can even help him if he wants. A scuffle ensues and Sam is able to kill the man. But that still leaves one x-factor floating around: Werewolf Rachel. Will he have to kill his wife? And is that something he’s wanted to do all along?

I don’t know what I was expecting here. But I definitely wasn’t expecting something this dark. This story is f&%$ing dark dude. DARK. Right from the start, these two don’t like each other. It’s not a casual dislike. It’s a deep dislike. So you’re trying to figure out why that is.

Baker, who’s a really good writer, baits you with a few misdirects, making you think Sam is the werewolf. So when it turns out to be Rachel, we’re surprised. As he’s gradually revealing all the toys in the story, he’s keeping you primed with this mysterious stranger who keeps showing up wanting to know where Rachel is.

Even the scenes that have the potential to be boring, like when the girls are stuck up in the attic, contain entertainment value. They start looking through old pictures kept in boxes and find out they had a brother. Where is that brother now? It doesn’t take long to add 2 + 2. I told you. This story is DARK.

I must reiterate how valuable it is when the writer can stay ahead of the reader. It’s even better when the reader THINKS he’s ahead of the writer only to be proven wrong. Which is what happens here. I thought I knew how this was going to end. I was wrong. And it really solidified the writer’s commitment to writing a TRUTHFUL DARK tale. He was never going to “Hollywood” this up. Maybe Landon and the studio change that in the movie but they shouldn’t. The ending is perfect.

Strangely, you know what this story reminded me of? Anatomy of a Fall. For those who haven’t seen it, the story is built around this marriage that completely fell apart. Crumbled on every level because the husband and wife hated each other. This is the werewolf version of that movie.

I wouldn’t be surprised if Landon saw Anatomy of the Fall, was then pitched this book by coincidence, and he realized that he could capture that same dysfunction and collapse of a family, in the form of a werewolf movie.

For those still struggling to come up with their own short story, one of the ways to write these is the way Big Bad was written, which is create ONE BIG SCENE. The family is at the house. The wife is turning into a werewolf so she needs to be tied up. A mysterious dude shows up at their door. There’s your scene. Have fun. And that’s exactly what Baker does. She milks every crevice out of that scenario. I would go so far as to say nobody could’ve written it better.

Also, a big reason why this worked – and this is something you can do a lot more in short stories than you can in scripts – is it gave the reader more detail about the world and more detail about the past. You can go into how Rachel and Sam met. How they were once happy. The specifics by which they were happy (meeting at school – were both hotshot academics). And really detail how they got to this point.

But it’s not just providing the facts. It’s providing the facts in the most dramatically advantageous way possible. Give us a little bit here, but not enough to form the entire picture. Just enough to make us curious and to get us to start forming that picture in our head. Then wait until 4 pages later to give us a little more information.

For example, we show the kids looking through the pictures. Then we see some little boy with dad. Who’s this boy? Don’t give us the answer yet. Cut back to Sam looking for Rachel. Four pages later, show the girls discussing this boy, trying to figure who he is. Only then do we start realizing – this was their brother and Rachel killed him. THAT’S why their marriage is so bad. It’s pretty hard to be happy when mommy murdered your son.

Another thing that stood out in the writing was that everybody was DOING SOMETHING when the story began. Bad writers start their characters’ lives as soon as they write “FADE IN.” Good writers know exactly what those characters have been doing for the past year, for the past month, for the past week, yesterday. (This is why I had you guys doing all that pre-script character work this week!!!)

That may not seem important. But when you read this story, you learn exactly why it *is* important. Since Baker knew exactly what was going on in Rachel and Sam’s lives, she could place them in situations where they’re DOING THINGS when we meet them. Things that matter. It makes SUCH A DIFFERENCE.

Someone needs to change the cover of this book. Cause this cover makes this look like it’s going to be a YA book. But this is one of the darkest stories I’ve read in a year. Wow.

[ ] What the hell did I just read?
[ ] wasn’t for me
[ ] worth the read
[x] impressive
[ ] genius

What I learned: Usually when I write these “What I Learneds,” I’m regurgitating things I already know. They’re important things – things that help screenwriters. But I’m no longer always learning something new from a script. This story was different. I genuinely learned something. Create a disturbance at the beginning of your story. A town that is going about its daily business is boring. A town that is cleaning up after a devastating landslide – that’s more interesting. It gives your location and your story an immediate energy cause everybody’s reacting to what just happened. I’m definitely filing this one away. Create a recent disturbance to your story’s location to start your story off with an extra spark of energy.

Genre: Comedy
Premise: A couple on the brink of divorce sets off on a romantic getaway to save their marriage, but when they find that they have inexplicably traveled back in time, they decide to team up to stop their younger selves from ever getting married.
About: This script finished Top 20 on last year’s Black List. The writers of the script have been writing together for over a decade. While they have made some shorts and a low-budget feature, this is their first big screenwriting break.
Writers: Mario Kyprianou & Becky Leigh
Details: 111 pages

Feels like a Paul Rudd part!

A little time travel always gives me a case of the cosmic goosebumps. That and a fresh-off-the-grill double-double from In-And-Out. If only those bastards delivered.

It’s rainy here in LA. I’ve got that milky-gray light bleeding through my windows – the kind that makes you want to read. Which is perfect for a guy who runs a website about… reading. :)

Married couple Jon and Ellie Landau have just turned 50 and are heading back to the place where Jon proposed to Ellie – Hawaii. Back then, when they were in their 20s, they were madly in love. But these days, Jon seems to be more turned on by his latest phone alert than he is his wife’s ass.

Ellie feels this, which is why she suggested this vacation. It’s the last chance to rekindle their love. And they get things started right away! Ellie suggests they do a repeat of their initiation into the Mile High Club, only to learn that pulling off sex in the airplane lavatory isn’t as easy, or fun, as it was when you were a horny 23 year old. Let’s just say this attempt ends with the Sky Marshall banging down the door.

Once at the Hawaii airport, the two walk by a play where the head actress, an old woman, appears to put some sort of spell on them. The next thing they know, everybody’s smoking cigarettes and their phones don’t work. They shrug it off and head to the hotel, which looks exactly like it did 30 years ago.

But it isn’t until they spot their younger selves that reality sets in – they’ve been transported back 30 years to the exact week when their young selves came. After a very difficult conversation, Jon and Ellie realize that neither of them are happy and that they probably would’ve had much better lives had they never gotten married to each other.

So they bestow it upon themselves to stop Young Jon from proposing to Young Ellie. And, while they’re at it, they decide to incept their younger selves with a dose of advice. For Young Jon, Jon will make sure he pitches his Amazon-like idea (before there was Amazon) to Future Fest. And for Young Ellie, Ellie will get her to pursue her writing career that she abandoned. To achieve this, they’ll have to befriend their younger selves. Along the way, however, they just might realize that they’re happier than they think.

I like this idea.

It’s like that George Clooney Julia Roberts thing from 2022 but more clever. In that movie, they were trying to stop their kids from getting married. Here, they’re trying to stop themselves. It goes to show that every idea has numerous iterations you can choose from and it’s worth it to explore those options before committing to your original one.

But how about the execution?

When I read a comedy, I need to start laughing immediately. I don’t know if I’ve read a comedy where I didn’t laugh at all in the first 10 pages and then I was laughing a lot from that point on. That’s why it’s so easy to judge comedy scripts quickly. You know if you’re not laughing during those first couple of scenes, the script is a dud.

And I laughed a lot in this opening scene. The writers take a well-known scenario – the mile-high club – and put it under the comedic microscope. The mile-high club sounds good in theory. But how does it work in practice? What happens if the bathroom smells from the last person in there? What about if there’s pee all over the place? How do you situate yourself? Especially if you’re older and less flexible?

And then there’s the comedic contrast – the scene is comparing the past to the present. They did this before, when they were in their 20s. But when you’re in your 20s, you’re not as aware. You don’t think about sanitary issues. You just go in there and do it. But after growing up and understanding how things work, you’re aware of EVERY little potential ickiness. That contrast is what makes the scene funny.

So the script grabbed me right away. And while the laughs don’t come as frequently as in that first scene, there are still some solid LOL moments going forward.

But here’s the thing…

The writers make the mistake of allowing their plot to take precedence over their comedy. I only realized this in the last couple of years: People come to a genre to get THAT GENRE. They come to horror to be scared. They come to action movies to see action. And they come to comedy to laugh. If you’re prioritizing anything else in the script over the thing that the reader showed up for, the reader’s going to be disappointed.

I just talked about this with a writer in a recent script consultation. He’d written a comedy and he had this big giant twist at the end that he really wanted to make work. And I asked him, “When’s the last time you went to a comedy and left excited about a twist ending?” It’s never happened. When you go to a comedy, all you care about is whether you laugh or not.

So with The Getaway, the writers inject two major plotlines – 1) stop Young Jon from proposing to Young Ellie and 2) have Jon get his younger self to create a great pitch at Future Fest so that he becomes rich and successful. That may sound like a good idea since it gives your characters something to do, which keeps them active.

But if the machinations of that plotline are too elaborate, then you’re spending more time explaining the storyline than you are writing funny scenes. You could feel that here. We’re so focused on getting Jon to get his younger self to like him so he can get him to pitch his Amazon idea that finding funny scenes gets left behind.

I’m starting to think you need to approach comedy differently than any other genre. Coming up with a plot that’s amazing, even coming up with amazing character arcs, isn’t as important as writing funny scenes. So when you come up with a comedy concept, brainstorm 50 funny set-piece scenes that best take advantage of your concept (yes, I said “50”), settle on the top 5, and build your story around those five set-pieces (as opposed to outlining a plot and trying to find comedic scenes along the way).

I know this is the better route because the funniest scene in this script is the first scene. And a big reason for that is that the plot hadn’t kicked in yet. So the writers could focus on writing the funniest scene rather than finding a funny scene within their plot.

Once the plot began to control them, then they had to write super-goofy scenes that weren’t that funny and didn’t make sense (riding in a helicopter and getting barfed on by someone from a separate helicopter). That’s what happens when you’re constrained by plot.

I’m going to finish this off by saying one more thing. In certain screenplays, there’s an opportunity to add a work subplot. Like here, we get this whole work subplot where Jon is going to help Young Jon pitch his Amazon idea to Future Fest. This subplot is the definition of an unneeded subplot. How do I know this? Cause I could ask 100 people who’ve read this script if they cared whether Young Jon succeeded with his pitch or not and all 100 would say no.

Again, THAT’S NOT WHY WE’RE COMING TO THIS MOVIE. We don’t care if Jon nails the pitch. You only want to include a work subplot if it has significant importance to the screenplay working. If you removed the subplot in The Getaway, nothing changes. That’s how you know it’s not needed.

The prototypical way to pull a work subplot off is Pretty Woman. They tell you just enough about the work subplot so that the m movie makes sense – it’s the whole reason Richard Gere is in town for a week and why he needs to hire a prostitute – and not one minute more. It’s there to help things make sense and that’s it.

Whereas, here, it’s impeding the actual fun of the script. We’re here to see if these two break their younger selves up. We’re not here to see if they do better at work. That’s nowhere on the poster. I want every screenwriter to internalize this. Only include the story beats that you promised us. Don’t give us ones we don’t care about. And ESPECIALLY don’t give us subplots that force you to make your screenplay more boring.

This script started out strong. These writers have comedic chops. But they focused too much on plotting and, in the process, lost too many opportunities to be funny. I do like that the writers are using the story to try and say something about the choices we make in life and how they can lead us down completely different paths. But that should not have been the priority. The priority should’ve been the comedy.

[ ] What the hell did I just read?
[x] wasn’t for me
[ ] worth the read
[ ] impressive
[ ] genius

What I learned: Relationship scripts work best when the writers lean into the TRUTH. Whenever you give us moments that feel truthful and representative of what happens in real life, we will connect with it. There’s a brilliant little moment early in the script where Jon and Ellie are excited for getting upgraded to the Penthouse suite. They can’t wait to get some dinner at the fancy restaurant downstairs. We then hard cut to them at the dinner table in silence. Why? Because they have nothing to talk about. Why do they have nothing to talk about? Because they’ve spent the last 30 years together!  This was the most truthful moment in the whole movie. It captured marriage in just 10 seconds. And it did so because it leaned into truth.  Leaning into truth ALWAYS MAKES YOUR SCRIPTS BETTER.

In today’s post I reveal something that very few screenwriters know – which is the number one thing that leads to a boring script.  And it’s going to shock you.

This weekend’s weak box office is relevant to today’s conversation – specifically the box office failure that was I.S.S. – because I’m going to talk about how to avoid writing a boring script. The 2024 Two-Script Challenge is upon us. We’re starting Screenplay Number 1 next week. So I want to show you guys how to avoid boredom and even achieve the opposite – the big thing that makes a screenplay exciting.

I.S.S. came out this weekend and barely made 3 million dollars. I reviewed the script a few years ago and identified the main problem all the way back then for why it wouldn’t do well.

It was boring.

I’m not roasting the film’s box office because it didn’t have much of a marketing push. First weekends are almost always about how big the marketing push is. This film got very little of that. I’m more focused on the audience score, a C-. C- in audience score parlance is the equivalent of an F- -. It means the audience really disliked the film. And I know why. Because the script was boring. Check out my old script review to get some more context as to why the film was doomed.

But we’re talking about a different movie today: the big-budget Netflix movie, “Lift.” “Lift” is an exceptionally fun idea, one of the better concepts I’ve come across in a while. A team of bad guys are going to pull off a heist on an airborne airplane. That’s a “licking your writing chops” type of screenplay. The possibilities are endless.

And yet, the final script is so devoid of entertainment, we’re left to wonder, what happened??

For those who haven’t seen the movie – and that appears to be most of America – it follows a mastermind named Cyrus who steals a lot of high-value things. He works with a team of heisters, the most memorable of which is a guy named Denton, who’s weird and a master of disguise.

When Interpol agent Abby learns that an international terrorist is transferring half a billion dollars worth of gold on a plane, she realizes that if she can steal his gold, she can prevent him from funding any more of his terrorism. So she (at her boss’s urging) gets Cyrus (who she once had a fling with) to come up with a plan to steal the gold in-flight. Cyrus recruits his team and they prepare for the most impossible heist in history.

Sounds fun, right?

Yet, by every metric, the movie doesn’t work. It’s got a 5.5 on IMDB, a 30% RT score, and the most damning metric: a 31% audience score. This is a movie made for the audience, not the critics. That score hurts badly.

But here’s the thing. The movie isn’t bad. Bad is what happens when you take a big swing and whiff. It’s Battlefield Earth. It’s Southland Tales. It’s Howard the Duck. Lift suffers a much worse fate: It’s boring. And today I’m going to teach you about the number one thing that makes a script boring. Because you’re about to write your first script of 2024 and I want to make sure it doesn’t suffer the same fate as Lift.

Who here thinks they know what makes a script boring? The number one thing. Everyone stop reading and go make a guess in the comments. You’re not allowed to re-edit it. When you’re finished, come back up here so I can tell you what it is. Cause I know. I’ve read enough boring scripts to be able to tell you the exact reason. And that reason is going to surprise you. Cause it surprised me when I first figured it out.

Are you ready for it?

Are you sure?

I don’t think you’re ready. But I’m going to tell you.

The number one thing that makes a script boring… IS WHEN IT’S WRITTEN WELL.

Wait, what??

That can’t be right. If you’ve written a script well, you’ve done a good job.

No, actually, you haven’t. All you’ve done is give the reader the exact experience they were expecting. And that’s what makes a script boring. Cause readers don’t want to get what they expect. They want to get what they couldn’t have come up with themselves. They want to be surprised.

And if all you’re doing is checking screenwriting boxes to get your script written, what you will have is a technically proficient script without any soul. It will get the job done but it will feel empty.

As I watched Lift, I noticed that the writer was doing the technically correct thing every step of the way.

We get the big flashy opening set piece to pull us in – a heist of an NFT. We introduce our mastermind and our Interpol agent, who once had a relationship together, and now must team up for this heist.

The heist itself is impossible. Getting onto a plane mid-flight to steal 150 tons of gold is as hard as it gets.

We then introduce all these little smaller problems that the heist team has to solve in order to achieve the ultimate goal. All that is exactly what you want to do in a heist film. It’s about the team trouble-shooting to pull off the heist.

Those are just the basics. There are tons of other character-related things (bringing in a “wild card” character in Denton) that are technically correct as well.

That’s what’s so frustrating about screenwriting. Is that you can do everything right yet still write a weak script.

But how can that be true?

Well, one of the things I’ve said before but I probably need to say more often is that a script’s strength is not in the things that the writer does right. It’s in the risks that the writer takes that have the potential to be “wrong.” You see, it’s the blemishes that make a movie stand out. A perfectly smooth face is boring to look at.

Look at Joker. That entire movie is built around something you’re not supposed to do in screenwriting – which is to make your hero an unstable psychotic murderous person who isn’t easy to like. That was a HUGE RISK. Which is exactly why, when it worked, it worked exceptionally, making over a billion dollars.

Promising Young Woman came out during a time when it wasn’t considered okay to make female characters “crazy” or possibly be in the wrong. That was a huge risk. Yet that’s exactly what made the character so interesting. If they would’ve made her yet another Mary Sue who could do no wrong, which was considered the “right” thing to do in screenwriting at the time, the script would’ve been boring.

Now, I know what a lot of you are thinking. Those are artsy movies where it’s easier to take risks. That’s true. In fact, concepts like Lift are the ones MOST SUSCEPTIBLE to being boring because they’re mainstream and, therefore, don’t allow for a lot of flexibility in the creative part of the execution.

But I promise you this. If you don’t take SOME RISKS in whatever script you’re writing, your ceiling is a boring script. I say “ceiling” because you might not even get the script to the point where it makes sense, which happens a lot with newbie writers. But even if you execute it perfectly, without risks, it’s going to be boring. Cause a million movies have come out just like it, and by following their formula, you haven’t given us anything new to celebrate.

So you have to take risks. You have to try some things. One of the best recent examples of a mainstream script taking a big risk was Spider-Man: Homecoming. That whole thing where Mary Jane was the Vulture’s daughter – that could’ve gone horribly wrong if the audience didn’t buy it. I’ve seen versions of that choice in other movies where the audience violently rolled their eyes while mumbling “Give me a break.” It was a big creative risk. And, as a result, it’s the thing everyone remembers about that movie.

So you have the ability to be risky in these scripts. It’s just harder. Just don’t let that deter you. A boring script is the worst version of a script you can write. Not just because no one will remember it. But because it actually takes a lot of effort to write a perfectly proficient script. And then you get no reward for it. You might as well take some risks along the way so that the script has a shot at being memorable.

Feel free to share some notable creative risks you’ve seen in big films in the comments section. Cause I know most of you are writing marketable Hollywood movies for the 2024 Challenge. So I want you to see how other writers of these films have taken risks that have paid off.

One of my favorite characters from 2023 (Duncan Wedderburn in Poor Things)

Week 1 Post
Week 2 Post

Okay, it is WEEK 3 in our WRITE TWO SCRIPTS IN 2024 Screenwriting Challenge. Week One was playing with possible concepts. Week Two was solidifying a concept. And now we’re on to Week Three – FIGURING OUT YOUR CHARACTERS.

Usually, when writers write scripts, they start writing IMMEDIATELY after they’ve come up with their idea. This is almost always a mistake. When you jump into a script too quickly, you burn out fast. You’ve got a runway of about 20-40 pages but you never build up enough speed to take off.

You erroneously figure your premise is too weak and you abandon your script like an alcoholic abandons their family. Whoa, that just got dark. Disregard that. Actually: REGARD IT. This post is about character. And character flaws are crucial to understanding your next steps.

This is the part of script-writing NO ONE WANTS TO DO – the character work. It’s boring. It’s hard. It doesn’t allow you to have any fun, since it’s all backstory and, therefore, doesn’t fill up any pages. Yet, it’s probably the most important work you can do for your script.

In my experience, getting the characters right is the single most important aspect of a screenplay. You can have a bad plot, but if you have great characters, you can write a good screenplay. Meanwhile, if you have bad characters, even if you have a great plot, the screenplay will suck. The reader will not care what happens unless they care about the people taking us there.

If you create a character who we like, give them some kind of resistance within them that they’re battling, and show them succeed – if you get that right, NOTHING ELSE MATTERS.

However, we need to do a deep dive to get there. I don’t need to know when your character had their first kiss (unless it’s relevant to the story) or what their favorite food is. That stuff does help. And if you want to do that work, I’m all for it. But I’m looking for something more important.

Here’s what I want you to do this week. You’re going to make a list of your 4-5 major characters – the ones who have the most screen time. You’re then going to figure out the five major character pillars of each. These five pillars are…

Likability

Personality

Flaw

Arc

Central Relationship

Let’s go through these one at a time.

LIKABILITY
I got news for you. If we don’t like your main character, there’s a very good chance we won’t care about ANYTHING they do. Which means you can write the greatest story ever and we’ll still hate it because we don’t like the person. Go back through all your least favorite movies and I can pretty much guarantee you didn’t like the hero. So you have to figure out why your character would be liked by others. And no, you don’t get to ignore this one if you’re writing a dark comedy and your hero is a tough pill to swallow. You then have to figure out how to make your hero sympathetic. If they can do it for Joker, you can do it for your script. You want to have such a solid reason for why your hero is likable or sympathetic that, if you were taken to court on the matter, you would win the case hands down. That’s how persuasive your argument should be.

Here are a few recent movies and why their characters were likable or sympathetic. Willy Wonka – The nicest kindest person you’ve ever met. Ken in Barbie – All he cares about in life is getting this one person to notice him but she won’t. We can all sympathize with that since we’ve all had that person (people) in our own lives. John Wick – He’s sympathetic cause his wife died and they took his dog. He’s also likable because he’s a nice guy with good morals. Robert McCall (The Equalizer) – One of the most likable characters in movies because all he cares about is helping people who can’t help themselves, to the point where he’s willing to risk his secret identity to do so. Louis Bloom (Nightcrawler) – He’s the ultimate underdog in this night-crawling business (audiences love underdogs) and he’s obscenely driven (audiences love characters who are driven, cause driven people are active, and audiences love activity).

PERSONALITY
This is one of the most overlooked aspects of character creation in screenwriting and if you don’t pay attention to it, you are likely to have a boring main character. This happens ALL THE TIME in the amateur scripts I read. The writer makes all the surrounding characters fun and interesting but they assume that their main character needs to be so grounded that they don’t have any defining traits whatsoever. Which is a huge mistake. You have to give your character some personality.

The best way I know how to do this is to figure out your character’s sense of humor. Your sense of humor dictates the majority of your personality. Are they sarcastic? Do they like gallows humor? Are they goofy? Are they the “dad joke” type? Are they deadpan? Are they quick-witted?

Going beyond the humor, what other aspects do they bring to the table that help them stand out in a conversation? Are they sexy, like James Bond, who has that twinkle in his eye whenever he speaks to a woman? Are they intimidatingly smart, like Robert Downey Jr’s Sherlock Holmes? Are they cocky? Are they charismatic, like Ferris Bueller? Are they quirky, like Bella Baxter (Poor Things)? These are just some ways to identify your character’s personality. Define it as tightly as you can because if you don’t, your character is going to sound untethered. We’re never going to have a good feel for them.

FLAW
This is obviously a big one because it’s the thing that most defines your character within the context of your movie. Writers can get tripped up by flaws. But they’re easier to figure out than you think. The character’s journey in the movie will determine how you identify their flaw. For example, if the movie is about a banker trying to get rich, the flaw will probably be greed. If the movie is about being the best at something (Nightcrawler), the flaw will revolve around recklessness or perfectionism. If someone wants to be the best at all costs, that’s their flaw – they don’t know when to stop. If the movie is about a “my way or the highway” coach who’s trying to take a basketball team to the championship, the flaw would be stubbornness. He’s not able to listen to anyone else but himself.

Think of the flaw as the NEGATIVE part of your character’s personality. They have good things. But this is their one bad thing. And it’s usually the most dominant part of their personality. Some writers have asked me if addiction is a flaw. It can be. But it’s usually what leads to the addiction that’s the flaw. So if someone struggles to connect with others but can connect with them when they’re drunk, then they might develop an alcohol addiction. But it’s not the alcohol that’s the flaw. It’s their fear of connection. That’s what they need to overcome. Not the alcoholism.

ARC
Now that you know the flaw, you have to figure out how you’re going to arc your character over the course of the story. A well-constructed character arc is one of the most satisfying storytelling experiences an audience can have. We audiences love to see that broken character overcome that flaw that’s been holding them back the whole movie (which we extrapolate to mean ‘their whole life’) and finally change. It’s not the good guy beating up the bully at the end that gets us. It’s that our good guy’s flaw was that he was a coward and he’s finally overcome that cowardice to become brave, which gave him the strength to stand up to bully at the end. THAT’S WHAT GETS US. When George McFly punches Biff after being Biff’s punching bag the whole movie, we cheer because George has finally overcome his flaw, his cowardice.

Unfortunately, an arc isn’t just about establishing a flaw at the beginning and having them overcome it at the end. There’s all that in-between time as well. This is your second act and you want to set up three to four big scenes where your hero is faced with the opportunity to overcome their flaw but they fail. We need to see these little failures along the way for the big final change to feel genuine. So, as you’re constructing the arc, I want you to think about these 3 or 4 scenes in your script where you’re going to challenge your character’s flaw. And then, also, figure out what that final climactic scene is going to look like where your hero is faced with that opportunity to change once more and he finally does.

CENTRAL RELATIONSHIP
There are no characters in a vacuum. You can’t express a character unless they’re bouncing off other characters. So you want to figure out what the central relationship in your movie is, then strategize how to get the most out of it. For example, in Titanic, the obvious central relationship is Jack and Rose. You don’t want to wait until you start writing to figure out how that relationship is going to work. You want to identify what the major source of conflict is in that relationship so that whenever the characters are together, they’re dealing with that conflict.

In that movie, Jack’s the kind of guy who lives by the seat of his pants. He does what he wants to do whenever he wants to do it. Rose is the kind of person who plans 8 moves because she has to. She’s in a prison – a bunch of rich people who live a highly structured life. And that’s what makes their relationship interesting. Their worldviews are opposite. If James Cameron had envisioned Rose as this cool chick who is more of a rebel, then Rose and Jack are too similar and you don’t get as much conflict. More recently, you can look at Tony Stark and Steve Rogers. Stark is willing to get dirty to get the job done. Rogers plays by the rule book. Those worldviews are what creates the conflict that drives that relationship.

Figure out these five pillars for, at the very least, your hero and your biggest secondary character. If you can extend it out to more characters, even better. I promise you that the more you know these five pillars, the more confident you’ll be going into your script. What you have to remember is that there’s the story being told by your plot (Save Barbie Land) and the stories being told within your characters themselves (Ken – must overcome his feelings of worthlessness and find purpose if Barbie doesn’t want him). If you can create a great character story, your script will be impervious to plot issues. I know that sounds crazy but it’s true. To this day, Swingers is one of my favorite movies. It also has one of the worst plots I’ve ever seen in a script. But it works because the characters all have their clear through-lines.

Okay, get to it! Next Thursday, we’re outlining our plot. Which means that, yes, you finally get to start writing your script in Week 5. Can’t wait!