What defines a Masterwork?
8 Dec 2025 · 13 min
Sean Coyne defines masterworks on two levels: books that endure across centuries like Pride and Prejudice, and personal masterworks that shape a writer's sensibility. He recommends studying genre-specific examples, comparing old and new works to understand craft conventions at the scene level.
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Hello and welcome to the Story Grid podcast. This is a show dedicated to helping you become a better writer. I'm your host, Tim Grall, and I am a writer in the Story Grid universe. Joining me shortly is Sean Coyne. He is the creator of Storygrid, the author of the book Storygrid, and an editor with over 30 years experience. This week we have a great question from a listener about how to define masterworks. So, you know, if you've been around Storygrid for very long, we talk a lot about studying masterworks, but how do you know if a book is a masterwork? So that's what we dive into this week. So let's jump in and get started. So, Sean, we got a question here from Rebecca. She says what defines a masterwork? It can't be just a bestseller, as books can simply hit the zeitgeist of the moment. Is it a book that's lived beyond the author? Then what about contemporary masterworks? If the line is books everyone associates with that genre, how can people who never experience that normal exposure or traditional education figure those out? So how do you define a masterwork? And I would say, too, especially if I'm wanting to study masterworks to become a better writer, like, how do I know which ones to pick?
Okay, well, whenever you have a category of something, you have to think about, what kind are we talking about? And then when you have the kind of thing of category, then you start talking about degree. So the kind of masterwork that we're talking about has many, many different definitions. So there's high resolution definitions where I could talk about the. The granular detail of the movement from scene to scene, even beat to beat, and why that masterwork is operating at that level of granular detail. Now that. That's not for everyone. That's probably for a very small number of people. So, in fact, that's kind of what I'm working on right now is defining that granular detail in the laboratory with some colleagues. So that's one thing. So the global masterwork conception came out of the following idea, right? My idea was, hey, people want to get better telling stories, and they want to be able to judge how well they're telling a story. Okay, cool. How do we do that? In a way that is not just some guy named Sean Coyne saying, you know, this isn't good enough, or some editor in New York that you've never met, or some agent in New York saying, hey, you know, this just isn't for us because it's not good enough. Because that leaves the person who's created the story in a real quandary, because they're like, well, can you explain to me what is good enough? So the definition of masterwork that I came up with for Storygrid was, hey, if we were able to take a poll, say we were able to get 100,000 people to judge whether or not a story was really great and one that they would recommend to other people, what would be that category of book? So a masterwork at that definition would be really thinking about, is there such a system that created that kind of pull? And you know what? We have one, and it's called the Bestseller List from Time Eternal. So when you're looking at a bestseller list, you can look at, well, is it a bestseller this week? Because that's sort of like, well, it's caught the eye of people last week. All right, well, what about all those books that were bestseller bestsellers for longer than a week? Maybe those, you know, attracted the eye of more and more people, and the word of mouth was better. Well, what about those that were for a month? Okay, what about a year? What about two years? What about five years? So you can see the degree of bestseller that I'm talking about is getting tighter and tighter. So there's smaller and smaller numbers of books that we can say have been best sellers for a year. What about five years? That's even smaller list. What about 100 years? Oh, that's a very small list. That's a really shiny object that we can pinpoint and say, hey, that's a masterwork that generally everyone in and through time like it was a bestseller. It doesn't even matter if it was a bestseller in its time. It lasted, right? So it lasted in and through time. So that's how I define a masterwork at the highest level of coarseness, meaning the broadest category of kind of masterwork. So books like I Know why the Caged Bird Sings by Maya Angelou, books like Pride and Prejudice by Jane Austen, books like the Great Gatsby by F. Scott Fitzgerald, and on and on and on. I could. We all know these off the top of our heads. And if we don't, we can just Google, like, the greatest books of all time, and these things are going to pop up. David Copperfield, things like that, right? So once you have that list, that's a great starting point to compare and contrast how well you're telling a story versus a masterwork. So at Storygrid, what we do from there is we analyze the masterworks and get a diagnosis of what that masterwork did, and then we can use that and compare it to our work. So if we're writing a crime story, we're probably going to want to analyze a crime story that's a masterwork. What are those? Well, Sherlock Holmes comes to mind. Right. So you can find these masterworks pretty easily. It's not that difficult. And then use them, and you don't have to do it at the resolution of StoryGrid. You can just say, how does that compare with mine? Let me broadly outline what Scott Fitzgerald did in the Great Gatsby. Well, he starts with this guy telling a story. All right, what does mine start as? Am I telling a story like the Great Gatsby? Well, then maybe if I mirrored what F. Scott Fitzgerald did, then that would be closer to something that works than doesn't work. Now, obviously, we have many different forms of masterwork at Story Grid, and I. I don't want to spend nine hours going through the different delineations of masterwork and how we determine that. But it's not as difficult of a concept as you might think. And we can have personal masterworks. Right. So there are things that are very, very salient and wonderful to me that I would identify as masterworks in my life, stories that have changed my life. That if I said to Tim Grohl, hey, what did you think of North Dallas 40? You'd be like, I've never heard of that book before in my life.
Right.
But that was an extraordinarily influential book in my personal landscape of duration in my life. And I consider that story a masterwork in the realm of Sean Coyne. So we all have those. And those things are usually the ones that will lock us into the kind of story that we really should be telling, because they transformed the way we looked at the world when we were growing up or reading a particular story. So when I say to people, when you're writing a story, think about the book that you would wish that you could put your name on. Right?
Yeah.
And that way, that's Tim Grohl's masterwork. That's Sean Coyne's masterwork. And from that, it doesn't mean that you use that as the model for your story, but what it's going to tell you is the genre that you're working in. Like, North Dallas 40 is a performance story about football and sports. So that doesn't mean that I have to write. If I wanted to write a novel, I would write about football and sports. Although I could. I. I would say, oh, Performance story.
Right.
That's what's really salient to me. Maybe that's what I should be thinking about. Are there other super duper masterworks that have lasted throughout time that are performance stories that I could use to model my work? So masterwork is this beautiful nested Russian doll model that will enable you to afford you the ability to home in on the stories that are most important to you. So a lot of people, when they say, I don't know what a masterwork is, they're looking for this perfect definition that will solve all of the problems that they think are inherent with, like, well, Sean calls that a masterwork, and I don't. That's cool. That's fine. But you've got to respect other people's definitions of masterworks as much as you respect your own. And it is a little bit squishy. But I do believe that there are a pantheon of masterworks that we can use. These are the ones that last for centuries. Pride and Prejudice. I mean, how can you go wrong with that? I don't think anybody would say to me, you know, I think that's kind of a middling book. No, it kind of invented the modern love story that's 70% of our market. So to say that that's not a masterwork is kind of. I'll go to my grave saying that that person is. It's fudging. And they're not really playing a legitimate. You know, they're not having a dialogue about factuality. They're talking about a subjective instead of an objective evaluation of. Of a masterwork. I think there are objective evaluations of masterworks. And. And we are working toward being able to say, you know what? We've analyzed this objectively using some tools. Here's the objective demonstration of this masterful story. And if you disagree with that objective thing, then you need to analyze our process of establishing objectivity and show us where we went wrong. You just can't say, I don't agree and say, you're wrong, because I don't agree. You've got to actually examine the objective nature of our methodology. And now I'm getting too philosophical. But.
Well, I think if we're thinking through like you would never say to somebody, they should only pick one masterwork, and that's the only thing they should study. So to me, it should be something like, well, okay, if you're writing a love story, let's go with the one that we know is a masterwork. Jane Austen's Pride and Prejudice. And then if you want to go with something that's come out in the last 10 years, then you can look at, well, what's selling well, what's. What do people really love? What have you read that you love? So you combine this, like, clearly a masterwork with a personal masterwork, and look at them both, and you're probably going to learn something from both of them. And probably learn something by comparing and contrasting them, too.
Absolutely.
Because I thought it was interesting when, you know, we came out with the Masterwork Guide to the Murder of Roger Ackroyd. I was talking to Sophie, the author, and she was talking about how, on one hand, it's like, as conventional of a crime story as possible. Right? You got your master detective, you got your dead body, you got your red herrings, your clues that ultimately leads to a conclusion of who's the murderer? She's like. But then if you look at it from a different perspective, it was a heavily innovative crime story at the same time because. Right, so Sherlock always had Watson that was a reliable narrator, where in this one, it was an unreliable narrator. And then at the end, Perot didn't, like, drag Shepard. I think it was Shepard that did the murder, didn't drag him off to jail. It ends with the question, was justice actually served? Because he allowed him to commit suicide instead of taking him to jail, which is what he, quote, should have done. And she's like, so on one hand, it's as conventional of a crime stories you're ever going to find, but then from another perspective, it's completely innovated on the conventions as well. And I was like, oh, wow, that's just. That's so interesting.
It turns on the global value in a unique way. Right. So the global value of a crime story is justice, injustice. So what she did when she wrote the novel was to put a really nice tweak on what is just. Right, yeah. So the ending is a turn on what justice can really be. Is it just for someone to suffer because of somebody else's crime, or is it just to allow that person to make amends by, you know, I mean, killing themselves so that other people in the future won't suffer from their actions? Right, that was a really amazing twist. That is insightful. It's revelatory to the reader by the end. So not only do they learn, do they have the mystery solved?
Right.
Well, it's a problem. I mean, it's not really mysterious. Well, I don't want to get into the details of that. But that's the point is, like, it's playing on the global value at stake. So genres, again, it's super important to understand your genre because it'll tell you the value. And then once you have the value, then you go, how do I make this a little bit different? Like, people are expecting this kind of justice, and I'm still going to give them justice, but a new form of justice that's even more just than the justice that they thought they were going to get. Right.
Well, and I thought it was interesting, too, because when we came out with the one for Treasure island, the masterwork guide to Treasure Island, I was talking to Leslie and she's like, you know, there's. There is value in studying a book that's so old that you don't relate culturally to it anymore either, because you get to see it more clearly. Right? Because she's like, when you're looking at something that the language is different, the time is different, the culture is different. Like, just the when it was created was so different because it was the late 1800s. She's like, you can see what the author's doing more clearly because it's so different from. From what you're used to reading. She's like, where if you read a contemporary story, it's hard to really pick out some of these things because you're so used to them, because it's part of your culture. And I thought that was another, like, interesting take of why it's worth studying old novels that have stood the test of time because they're masterworks, but also because, like, they give you this. Every modern love story is just a modern telling of Jane Austen, you know, so it's just like. But reading Jane Austen allows you to see that more clearly than, you know, somebody got picked up in a bar and you're so used, you know, it's like that just didn't exist then. Thanks for listening to this episode of the StoryGrid podcast. For everything StoryGrid related, check out storygrid.com make sure you pick up a copy of the book and sign up for the newsletter so you don't miss anything happening in the Story Grid universe. Also, make sure you go to storygrid.com books and to see all of the titles We've released through StoryGrid Publishing. If you'd like to check out the show notes for this episode or any past episodes, all of that can be found@storygrid.com podcast. If you would like to reach out to us, you can find us on Twitter StoryGrid. And lastly, if you would like to support the show. You can do that by telling another author about the show and by visiting us on Apple Podcasts and leaving a rating and review. Thanks for subscribing and being a part of our work here at Storygrid. We will see you next week.