I spoke to James D'Amato about his new book, The Ultimate RPG Villain Backstory Guide. The guide is out today, grab it wherever books are sold! We also talked about his tenure on the One Shot podcast, the natural cause and effects of having too much money (hint: it turns you into a villain), and why you shouldn't handwave away the problems wealth can cause your villains.
Edited from a conversation on Friday the 13th, February 2026.
Alex: I am here with James D'Amato. You are the host of Skyjacks and the One Shot podcast.
James: The former host of One Shot! The current host of One Shot is Dillin Apelyan, who is my co-author on this book.
Alex: That shows how far behind I am on One Shot. You are also a professionally trained comedian and improv-er. Am I forgetting anything else in that introduction?
James: Part of the reason for the season is I'm also an author. I have published both books with Simon & Schuster's imprint of Adams Media and games that I've got coming out through Possible Worlds Games.
Alex: And you have a new book coming out very soon, in fact probably out today when this interview launches! We're here today to talk about the Ultimate RPG Villain Backstory Guide.
James: Yes, the original backstory guide came out close to eight years ago, and that is for player characters in the fantasy genre. We've since done editions that are for multiple genres, and now we're up to doing villains specifically to help GMs or people doing evil campaigns, or maybe even just anti-hero campaigns, making their characters a little morally compromised.
Alex: I want to get into that, since that is the reason we're here, but I want to ask a couple questions about the One Shot network. You mentioned you've stepped down as host now, but can you talk about what the goal of that podcast is, or why you started doing what you did with that?
James: I started this podcast over 12 years ago now, which is wild. The podcasting landscape looked very different, there were very few shows or streams or videos about tabletop role-playing games, and the few actual plays that were out there were shows that were primarily actually doing Pathfinder's Rise of the Runelords campaign. I was doing comedy podcasts at the time, and doing them on a network [ed: now defunct] called Peaches and Hot Sauce , and the head of that network came to me and was like, "Hey I'm listening to this actual play called Nerd Poker and I know you play tabletop role-playing games. Could you develop something like this for us?" My personal experience with role-playing games is that they can be so much more than just fantasy sword and sorcery adventurers, so once I looked around and saw that [the RPG podcasting environment was] either Pathfinder or D&D, I decided I wanted to focus on a show that shows off all of the things that role-playing games can be.
James: A big part of that is that I had such a great experience with role-playing games, and I didn't find them until I was in college. So I wanted to use my voice and use my abilities as a performer to help welcome people into the space and show them that, hey there are things that appeal to you here. Even if the most famous names, the household names in this hobby, aren't something that compels you, maybe there is something else in role-playing that you can like. And so all we did on One Shot is explore as many different role-playing games as possible with groups in a rotating cast that were hand-picked to support whatever game we were playing to put on an entertaining show that would maybe leave our listeners with the impression of, "Oh I liked that game and I can see myself playing it."
Alex: And I think you accomplished that goal. Thank you for that bit of background. But we're really here to talk about the Ultimate RPG Villain Backstory Guide. You mentioned anti-heroes earlier. Is this book aimed at GMs or players?
James: Mostly for GMs, though I do think there are players who might be playing an evil campaign, or, you know, more anti-hero characters. I think those people could also benefit from this book. But when I think of a villainous character, usually I'm thinking of an NPC that the GM is playing.
Alex: What was your inspiration for writing this book now? Did it come out of the success of the Character Backstory Guide, or or how did you come about this idea?
James: It definitely came out of our success with the character backstory series. They have been, since their inception, tools that readers have constantly mentioned to the publishers and in reviews as helpful to people in their process. Our backstory guides are not really focused on mechanics. They are all about how you develop the story of your character and using game mechanics, tools that people might be familiar with, playing Powered by the Apocalypse games or Belonging Outside Belonging games, using some of those tools to give people the ability to, by themselves, develop a backstory that will give them a little bit more juice to take to the table. It gives them something to go, "I know who this character is, and I have a better idea of how they got here."
James: So if you are somebody who just likes to play by yourself and you love your character so much you just want to know more about them, those exercises are kind of there for that. And if you want something more to draw on when you're at the table, that's kind of why we developed those exercises.
James: We, like I said, did the original backstory guide, which was mostly fantasy-focused. There were a few exercises in there that I think you could take to different genres, but fantasy was a big driver for that. The future guides that we did in the backstory area were about expanding it to different genres to give people more to draw on.
For this new one, we're going, how else can this concept be useful? What can we do to support people in a storytelling format? One of the things that came up as I was talking to my editor was villains and people wanting to give more personality, make the villains that they take to the table more memorable, and develop stories around those villains.
James: Just like with character backstory, I think creating backstory for NPCs really fills the game with these hooks that the players can pull on and can ground whatever you want to do with those villains in your game.
Alex: Now, you mentioned exercises in there. Are these solo journaling exercises or what's the shape of those exercises?
James: So there are a couple different ways that you can look at it. Some of them do have a workbook style in that there are questions and space to write in the book. So if you want to use the guide that way, as a workbook, or use it as a journaling exercise to write in a separate journal, it definitely works that way.
I tend to think of the material that we have in these books as exercises, mini games, and activities. They are all kind of expected to be interactive. In each of the guides, there's maybe a small section that is instructive and points you in the general direction of, "This is how you might develop a character." But the majority of the book breaks down villains into different categories and goes, "If your villain falls into this category, here is a specific thing that you can focus on."
If you walk through the questions, roll on the tables, or use whatever we've prepared for you, by the end of that exercise you're going to have something that exists in that villain's past and background that will inform their character and give them more interest and personality.
Alex: And you mentioned that this is not based on specific game mechanics. Does that mean I can use this for any system?
James: Yes, we try to be system-agnostic with these. The one thing we can't do is be genre-agnostic, because I do think the genres inform a lot of the flavor of these villains. If you strip things away, it actually kind of gets in your way creatively. So we try to make these informative toward different themes that you might be exploring by grounding them in a genre.
But the mechanics exist entirely within the exercise itself, so you can do this alongside another game system. Some of these are mini games, as I call them. They are kind of an RPG that you would layer on top of another RPG and sort of play along with the actual game that you're playing outside, again to help organize the thoughts and actions of characters.
Especially if you find yourself in a position as a GM where you are managing so many levers, you're like, "I really want to make sure that I'm furthering these plots along," or, "I am thinking about this when I present material to the table." So those games are sort of a way to manage that, much like the mechanics are a way to manage different actions and whatnot within any game that you might play.
Alex: And you mentioned that you're working on this book with a co-author. Can you talk to me about your process of writing with another person?
James: Absolutely. So for this book, I have the distinct pleasure and honor to write it with Dillin Apelyan, who is the person that I selected to succeed me on the One Shot podcast. I have been wanting to collaborate with somebody on a book for a while. To me, collaboration makes artistic expression so much more fun. It is what draws me to role-playing games and why it is my preferred creative output medium, because it's all about collaboration.
I think when you sit down with another person and you talk through ideas and you brainstorm, you come up with something that is so much better than what either person could do in isolation. So I wanted to work with Dillin for the joy that you get from a collaborative creative process. But also, at the time, I was designing Cosmic Century Knights, and I thought, if I am juggling a role-playing game at the same time that I am writing a book, it is going to be hard for me to hit the deadlines if I'm working completely alone.
So having Dillin there to tag team and work through this book made it a breeze! Instead of a nerve-wracking and stressful process, it was kind of a joyful process throughout, because I had somebody to work with and play with while I was writing this book.
Alex: That makes sense to me! Can you give me a teaser of what to expect, maybe share the piece of this book you're most excited about?
James: One of the things that I like is how we have broken down villains. When we were talking about villains and what is useful in developing them, I at first thought of genre. But when I was talking to Dillin, Dillin said, "Well, you know, there are a lot of different villain types that show up in various genres." I thought that was a really good point.
So we broke down our villains into the categories of Outlaws, Leaders, Believers, Opulence-based villains, and Supernatural-based villains. Your outlaw is your criminal. It is somebody who is a villain primarily because they are breaking society's laws. Leaders are villains because they are in — perhaps legitimate — power, but they are misusing the power that they have. You can see with a mob boss that there is a crossover between those. When we are looking at categories like that, the villain starts to get defined by the themes that it is carrying in whatever story or narrative you are putting them into.
I think that makes it a really useful angle for the book because a game master, or a player if they are developing an evil campaign character, can go, "These are the themes that I am thinking about. This is kind of the space that this character takes up within the moral framework of fiction." They can use that to mix and match different exercises that fit their character really well.
I really like that approach because of the way that I think it frees up readers to use the books in a lot of different scenarios.
Alex: I like that a lot! Is there anything else you want to share about the book?
James: Because you had asked for a sample of the book so that people can get an idea of what is in it, one of the things that we did for the Opulent — who is a villainous character primarily because they are extremely wealthy, and in fact so wealthy that just having that wealth creates problems in the world — is an exercise built around that concept.
Alex: There's some social commentary in there!
James: Some social commentary, yes, but I like to think of it as physics. There are certain forces that exert themselves in certain ways, and it is unavoidable at a certain point for a dense collection of wealth not to create problems and injustices around it.
And I find that, often, especially when you are presenting a villainous character in a role-playing sense, a trait like being extremely wealthy is hand-waved. Most of the time that is fine. I want to say this about any of the backstory exercises: they are not things that are explicitly needed. Anytime you hold a microscope to a specific aspect of your character and drill down on it, you will find more story details in there.
For the opulent, one of our exercises is called "My Holdings," which is literally a way to break down important assets that a very rich character has. We have a rolling table, but you can also pick. You define, "Okay, this is my primary asset. I own stock in this company." Because of that, I also own a collection of rare automobiles, or I happen to have an exotic animal that I am taking care of, or I have this piece of real estate somewhere out there.
We define those objects, and then we define how those objects create problems. They might be problems for your character. It is like, "Well, yeah, I technically own this huge, horrible monster, but it costs a lot to feed it. It's difficult to keep it contained and in place.
Alex: It keeps eating my henchmen.
James: It is a burden to me. It eats people. It actually causes this situation where I have to pay it in a certain way, in people. And it creates a storyline where, if this is the villain for your campaign, that suddenly becomes a vulnerability. Yes, it is dangerous. This is a beast that this villain could unleash against the party. But while it is not fighting them, it still exists. That means if you are a legitimate businessperson who society sees as legitimate, and your PCs are resisting this person who has legitimacy within society, you have to spend money and resources allocating them towards this thing.
And the problems that come along with that expose an area that is actionable for PCs. PCs can go, "He needs to move hundreds, like, of pounds of food. Maybe we cannot break into his compound, but we can waylay one of those trucks. And now he has a starving beast to deal with, and the chaos from that will allow us to do whatever the next step in our plan is."
All that exercise is doing is adding story to something that is normally hand-waved, to make it actionable for you as a game master, and for your players to interact with.
Alex: I really like how you've framed these vulnerabilities as potential story hooks.
James: Any fact that exists about your character is a potential story hook. Another exercise within the Opulent character is that, if you decide you have an old-money opulent and that money is mostly family money, there is a random rolling table for creating family members who may also have aspects of this fortune that you wrestle with occasionally or who come to you to cause problems.
This is definitely looking at it more [from the perspective of] "I am playing an evil PC," but you can always go, "Yes, the fact that I have this money is a driving part of my character, but I still have to contend with problems about it." I do have private access to a private island, but I have to go to my aunt, who hates my work or hates the way that I dress, and get access to that island through her.
All of that can be this delightful thing that just exists in the background, this is just for me, a way to play the game by myself, and enjoy my character. It's still in an interactive way, because the book is supplying information and ideas to you. [You can use it] alone, or you can be like, "Hey, I rolled up this crazy aunt, and I think it would be fun to interact with her. GM, can you please incorporate that into what we're doing?"
All of it comes down to this: anywhere that you look with a character, if you look closely enough, you will find the building blocks for stories that interest and excite you.
Alex: I really love the added texture of, "Is it really worth having to deal with Aunt Beatrice to get access to 'my' resources?"
James: And it addresses a problem that I find often with very rich characters, where you are having to work to justify them doing something. You have this character who says, "I am a billionaire", within the text of the game, I am a billionaire. "I can afford to hire a team of very capable people to deal with this problem. Why don't I?" Or, "I have a private island within my family name that we could set up our base on. Why am I not doing that? Why am I not just solving the problems that we have in front of our party?"
The answer becomes that there are other social complications. I can actually just solve this one problem, but it introduces Aunt Beatrice, who has a lot of finicky hooks that she can pull on to make other things difficult for you.
Alex: I love that. Is there anything else you want to mention?
James: The last thing I will mention, because One Shot did come up and I mentioned that Dillin has succeeded me as host recently, about a month ago at the time this is getting released, Dillin had his 100th episode as host of One Shot. He did a really beautiful game called Void 1680. It is essentially a game where Dillin is acting as a radio host and takes callers who are characters from the games that he has played during his tenure as host of One Shot.
It is this beautiful reflection on all the things that Dillin has done with that space and as host of that show. It is also a fun sampler. You can hear different characters and think, "I would like to learn more about that character," and they have an entire game attached to them.
I am excited to be working with Dillin in multiple capacities because I think he is wonderfully creative. I am so happy with everything that I work on with Dillin, this book and One Shot included, so I wanted to make sure that I pointed that out.
The very last thing to point out is that I do still host podcasts on One Shot. I am the current host of Campaign. We are approaching the final arc of the Skyjacks run of Campaign, which has been running a good long while.
The Ultimate RPG Villain Backstory guide is available now!