We love stories about badass vikings and ruthless bounty hunters, but it can be difficult to make them heroes worth cheering for. If the main character professionally hurts others for their own benefit, that’s a bit of a pickle. Fortunately, we know just the thing to keep readers from hating your hero’s guts!

Generously transcribed by Ace. Volunteer to transcribe a podcast.

Chris:  You are listening to the Mythcreant Podcast with your hosts Oren Ashkenazi, Chris Winkle, and Bunny.

Bunny: Hello, and welcome to another episode of the Mythcreant Podcast. I’m Bunny. And with me today is…

Oren: Oren

Bunny: …and…

Chris: Chris.

Bunny: Bad news, folks. This is awkward. Another podcast has hired me to eliminate their competition, and the competition is us.

Chris: Oh no!

Oren: That sounds very dark and edgy.

Bunny: Delete key has been sharpened and I am really angsting over whether to do this or not.

Chris: Well, at least you’re angsting.

Oren: Yeah. Very morally complex of you.

Chris: Yeah. I can be part of your dark backstory now!

Bunny: It’s possible I will fall in love with the Mythcreant Podcast instead. Or maybe I’ll succumb to my darker influences and ruthlessly tear down every mention of the podcast on the internet. What do I do? Maybe I’ll double cross the other podcast and assassinate them instead. I don’t know.

Oren: Anything can happen, really.

Chris: Or maybe we are also secretly assassins, so then we can have an assassin fight!

Bunny: I don’t know, it’s a triple cross!

Oren: Or it could just turn out that by coincidence, all the podcasts you’re hired to destroy have also done bad things and are bad podcasts that deserve it.

Bunny: Yeah, I’m a serial killer of serial killers. There’s a disconnect between the things we find cool and the things that are a little “morally yikes” when it comes to protagonists and heroes that are like mercenaries or assassins, and characters whose jobs are violent.

Chris: Bounty hunters or pirates are big ones.

Bunny: Yeah, pirates, crime lords, smugglers to a lesser extent.

Chris: Smugglers are, if you wanna avoid this problem, I think it’s pretty easy to make a smuggler okay. If you just give them a despotic government, you’re pretty much all set. 

Bunny: They’re kind of pirate lite.

Oren: I would argue you don’t even need a despotic government to make smugglers fine. You just have to make them smuggle cool things instead of dangerous narcotics. This guy’s smuggling iPhones, that’s kind of neat and harmless, versus this person is smuggling five tons of cocaine!

Chris: Just smugglers, smuggling in cheaper pharmaceuticals from Canada. Thanks, smuggler.

Bunny: Now that’s heroic.

Oren: Super easy. Barely an inconvenience.

Bunny: But yeah, mercenaries and assassins, and like, hired killers and Vikings and pirates are known for their robbing and plundering of innocents. So while we think these jobs are cool, they’re also kind of tricky to write because of all these bad things.

Oren: I just started a book that is about some characters who live in Scandinavia during the Viking age, and they’re talking about how excited they are to go on raids and how cool raiding is, and then they get raided and they’re like, “oh no, how could they raid us? That’s horrible. We hate it!” And there was just like zero self-awareness about this.

Bunny: Oh my gosh. You could do a social commentary there.

Oren: I guess you don’t like it that much. Interesting.

Chris: Were they calling their own raiding something else? Are they like going on visits and other people are looting?

Oren: No, they just called them raids.

Bunny: Yeah. The Vikings visited.

Chris: They were tourists.

Oren: They saved the jewelry from burning monasteries!

Bunny: While the lazy villagers just laid there in the grass.

Chris: So I can sum up what you need to make a character like this likable. It’s not exactly the same thing as whether they’re actually a good person. We do a little, like magician’s tricks to make it so they’re palatable to the audience. But you may still choose, if you have a conscience as a storyteller that you don’t wanna do this, but basically you need to not show them kill anyone who isn’t terrible, right? They can kill someone who just kicks puppies. And then you try to come up with a compelling reason why they do this job. Like if they were brainwashed, compelled, or forced into it in some way. Or they are an assassin for the revolution, which again ties back into “they kill people who are terrible or they’re part of a war.” Or you can just say it’s in the background. Have them stop doing it as soon as the story starts.

Oren: They’re totally a bounty hunter, except not really at all, because they immediately find a cool space baby, and they’re like, “this is my son now and I don’t do bounty hunting. That’s not a thing anymore.”

Bunny: A lot of stories with protagonists who are assassins or mercenaries or bounty hunters very quickly pivot into being a story that’s got a different central conceit than just murdering. So like, it might become a mystery or it might become a romance, like Grave Mercy did to me. And I’m still bitter about it 10 years after reading it because I wanted her to be a cool assassin and then she fell in love with her mark and it was very frustrating.

Oren: A surprising number of assassin stories that I’ve seen take place at Assassin School, which I would generally not recommend because any story set at a school has all the same problems as the magic school genre, but doesn’t have the novelty of magic. The novel Red Sister has this concept where they’re like at training to become assassin nuns. It is just so dull because yeah, they’re training, they’re training, and they’re training and there are occasional moments that are interesting where the protagonist is in danger of, you know, getting kicked out or you know, a bad guy wanting to grab her or something. So that does happen, but it gets really hard to have that be the whole story. You’re gonna end up with a lot of training unless you are very good at arranging the plot just so.

Chris: Having a single apprentice, I think, does work better for that because it’s a lot easier to imagine that the apprentice actually works on the job. So they can still do exciting things. Now granted, Assassin’s Apprentice was not a terribly exciting book, but that’s not because it couldn’t have been. This is a Robin Hobb series, which mainly, this one takes care of some of the morality issues by just having the main character fail. Like, he never successfully kills anyone.

Bunny: What if they were bad at it?

Chris: Well, there was one thing I liked, which is early part of his assassin tasks, he does the menial task of feeding zombies poisoned bread. ‘Cause they have a zombie problem. And it’s like, okay, I kind of like this. I kind of like the way we made being an assassin into a low-level menial job.

Oren: Yeah, another Robin Hobb book, Ship of Magic did the thing of like, “I’m a mean nasty pirate, but because of the circumstances of the story, I’ve ended up fighting the good fight.” And this is one of the few times I’ve seen that where I felt it didn’t work. It’s kind of tough to explain why. I think it had more to do with the fact that it felt like this character was just winning constantly by luck, and that was annoying. So I don’t think the premise was inherently flawed, but like that’s the thing that a lot of stories do. Red Sea under Red Sky by Scott Lynch has our protagonists meet a couple of cool lady pirates who, at this point in the story, are not killing a bunch of people to take their ship. They are instead defending their very cool pirate island from the evil bad guys. So great job, we can be friends with them and we don’t have to see them do anything too bad.

Bunny: Right. I mean, a lot of the reason we find vikings and pirates and assassins badass is just that they look cool. They’re generally, unless they’re failing upward, hyper competent in like skills that fantasy heroes have. Sneaking and being smart and being good at fighting, and they have cool weapons and they’re often like vigilantes, or at least they’re framed that way.

Oren: But also, Bunny, a good pirate never takes another person’s property.

Bunny: Yeah, robbing? A pirate would never!

Oren: That’s a meme, if you’re not familiar with it, from Jake and the Neverland Pirates, which is some comic that Disney put out a while back, or maybe it’s more of an illustrated book. Although when I was searching for it, I found this truly cursed, LLM-generated page saying things like “pirates have long been associated with plundering and pillage, but is it really true that a good pirate never takes another person’s property? The answer is a resounding no. In fact, the idea that pirates are inherently thieves is a stereotype that has been perpetuated by popular culture and literature.”

Bunny: Won’t someone think of the pirates?

Oren: This is just the perfect example of a terrible LLM-generated paragraph because every sentence makes grammatical sense, but when you put them together, it’s like, what does that mean?

Bunny: Pirates are being stereotyped because they steal!

Oren: And this is the kind of mistake that a human is unlikely to make because if a human is bad enough at writing to make this mistake, their paragraphs will also, like, their sentences will also be bad.

Chris: Let’s just not make a story about an LLM angsting as it murders the internet. Let’s not do that. We talked about Mando earlier, or referenced Mando. Kind of common one is they leave their job and then they start fighting their fellows. Mando stops bounty hunting almost immediately, and then he has to fight the rest of the bounty hunters, so that way we can also see that he is the most badass-est of bounty hunters.

Oren: Yeah, he’s the greatest.

Chris: Same with pirates, right? In a lot of pirate stories, the pirates just end up fighting other pirates. This happens in Pirates of the Caribbean, and Our Flag Means Death, and One Piece. They also make the authorities look bad, which in many of these stories can help, but in the end, they just end up fighting other pirates.

Oren: At least the parts of One Piece that I am familiar with. And, granted, there is a lot that I’m not, they kind of embodied “a good pirate would never take another person’s property.” They don’t seem to do that except for, I guess, the evil government. I guess they do take the evil government’s property sometimes, but like even then, it seems like it’s mostly an accident.

Chris: Yeah, it’s kind of hilarious, ’cause if you look at these pirate stories, you would wonder where the pirates get their money for their operations because they seem to only prey on each other.

Bunny: It’s just the same, like, hundred gold coins circulating.

Chris: There’s tons of lost treasure. They’d have to really be going for that like ancient lost treasure on a hidden island somewhere. Find one all the time.

Oren: What it actually is, is that there are pretty strict tax codes for treasure hunting. So they all register as pirates and then go hunt treasure to like, you know, avoid the burden.

Bunny: Or it’s like fishing. You have to get a permit, and then if you find a loot stash above a certain monetary value, you gotta toss it back. Otherwise it won’t propagate properly.

Oren: Bounty hunters are probably the easiest of these jobs we’ve been talking about to make not morally unpalatable, because you can just arrange it so that the jobs they take are always to bring in bad people.

Bunny: And they’re also bringing them in, not necessarily murdering them.

Oren: And of course, in real life, bounty hunters are not a positive good to the extent that they even exist. But in fiction, there’s never a shortage of super badass, serial killer arsonists who need to be brought to justice, and that usually works okay. Whereas assassins get a little weirder. In theory, you could do the same thing, but it’s just harder to create a scenario in which the good guys have an organization dedicated to secretly killing people. Not impossible, just trickier. And it’s easy for that to come across as fake or contrived, and that’s where you end up with a lot of problems that these assassin stories have where they either stop being assassins or they just quickly become too evil for you to care about.

Bunny: The Dead Cattail Assassins, which is a novela with a terrible name I read recently, kind of sidesteps several of these issues. Firstly by turning the assassination story into a mystery story, so we kind of shift the genre. Secondly, doing the thing where the protagonist has to fight the other assassins. And then thirdly, by making all of the contracts that the assassin takes, like, divinely ordained. One of the rules is the contract has to be just, and what’s just, well, if the goddess accepts it, so there we go. Morality handily sidestepped. They definitely justified the character’s quest that sets her off on the mystery with the person she was supposed to kill, but I don’t remember how, and I don’t know why the goddess approved that one. I think it was some sort of revenge thing, but that is another way to make it work is like, a very, very strict moral code or stringent rules.

Oren: Yeah. Although you do have to then come up with a plausible-seeming reason of like, why does this assassin group have such moral rules? Why would they not choose to be something other than assassins? Of course, having a God of assassins who is like “only do good assassinations” is a reasonable explanation, right? You can usually use gods to do a lot of things.  

Bunny: Right, in that story, assassins to this god signed away their afterlives, essentially, for a certain amount of time. In that setting, the assassins are like a dry cleaning service. They’re discussing leaving calling cards when they do an assassination so that when the person’s body is found, then handily there’s a calling card. If you want to get revenge on whoever ordered the first assassin strike, you can call the same assassins and they’ll do it for you. “I cleaned your shirt really well, and now they’ll spread the word!”

Oren: Word of mouth marketing is impossible to replace. You know, it’s, there’s nothing more valuable than that.

Chris: I read a romance recently that did the whole, “oh, assassin targets their love interest.” But in this one, the author wanted to come up with justification for the assassin actually trying to kill the other person in the romance, which requires a pretty strong justification. This one was creatively called Prince and Assassin. Do you know who the love interest was?

Oren: The jester, presumably.

Chris: How she does it is we have blood magic in the setting that can be used to control somebody. So we first establish that the assassin is under magical control and was kind of enslaved as a child and raised to be an assassin. So we can see that influence over him. When he’s sent out on this job, the blood magic can be used to kill him if he fails. But there’s another younger assassin that is threatened instead. So if he doesn’t succeed in killing the prince, then his little sister basically dies. If you have blood magic that can kill somebody instantly if they fail, and it’s now the little sister and then the assassin leaves, you know, Assassin School, we’ll call it, and goes out and has to kill this prince. The big problem I saw with this one is how the author would get out of that situation. So we have a really selfless reason why he will actually try to kill the prince even when their romance starts up and even when he doesn’t want to. But now we have like a lot of logistics involved, and I think that in order to make that story work, probably would’ve had to have brought it back to the assassin school where the sister was and where the master was, and where all the blood magic stuff was in order to arrange some situation when they got out of it. Instead, it was a little unsatisfying. We just said, oh, his sister never loved him. She was just faking it the whole time. And also the master decided not to kill her after all. So I liked the setup, but that kind of setup, that justified that action of trying to kill the love interest, was hard to pull off.

Oren: It might be worth addressing the authors who don’t want to make their characters the good guys and are like, no, I picked “mob boss pirate viking assassin guy” because I wanted them to be morally gray or straight up evil. And I’m sure some of them are around. And if you want to do that, you’re gonna have to find some other reason for your characters to be compelling though. And that’s, uh, challenging, not impossible, but it could be done. If you’re gonna do that, your story’s gonna have to have some other extreme draw. Like, this is a really grounded seeming retelling of mob violence. And then people who are into that will watch it regardless of the fact that there’s no one for them to cheer for and they don’t care who wins. That sort of thing. You can tell that the people who made The Book of Boba Fett were really struggling with this idea. We want him to be a mob boss, but we can’t have him do mob boss things and we don’t have anything to replace it with. So he just kind of hangs out for the whole show.

Chris: That actually reminds me of Blue Eye Samurai, ’cause there’s a sequence in Blue Eye Samurai where she is actually hired as an assassin. The person that she’s supposed to assassinate has been kidnapped and is in such a terrible situation that she will actually want to die. It’s a very frustrating sequence because then the main character gets there, finds out that she doesn’t wanna die, but because they’ve set up really big stakes for this assassination, where a whole bunch of people will be in danger if it’s not completed, kills the woman anyway, and then it turns out it’s all for nothing. This is, you know, designed to be just an edgy sequence of events, but I was not a big fan of it.

Oren: I don’t know if this would’ve worked if it had been well constructed, but it was so shoddily constructed, like, why did you even do this if you were gonna put so little effort into it? “Oh no, we have to kill this person. We can’t just kill the boss that abducted her, because then everyone will know. But also everyone will immediately know if we kill her. So you have to be super stealthy and secret.” Why can’t you just be super stealthy and secret when you kill the mob boss, the one who has lots of enemies, instead of the woman who has exactly one personal connection in this town? That scene was so bad, some of the worst writing I’ve seen in a long time, which was funny because it was on this beautiful animation, and then the writing was just like, “yeah, how can we kill this woman in the most agonizing way possible? And that’s all we care about, it’s lunchtime.”

Chris: I would say that a lot of the plot events that I would call edgy qualify in the same way. It’s not just that it’s dark, it’s just there’s something shoddy about the construction where it doesn’t feel like the darkness pays off and it feels like it’s contrived. The only reason that somebody died is because the storyteller just decided that they wanted something super dark and so they made them die, and that doesn’t feel like how the story would naturally unfold.

Oren: People talk about contrived happy endings all the time, but like a lot of sad endings are equally contrived.

Chris: If you had tweaked that, right, it’s not impossible to come up with a situation where somebody does something kind of dark, but it’s in some way justified. And you know, some people are not gonna like that, but some people do like dark stories. You can have a person who is technically supposed to be bad and have them be your main character if you make their killing like not on screen where it’ll emotionally affect the audience, and then maybe have some bad guys who are even worse. You can do a lot of sleight of hand if you want to, but if you want to have them kill an innocent person on screen, you are going to lose some audience members.

Oren: Because even if that had been perfect, I admittedly would’ve had some trouble with it just because I don’t really like that kind of story, and I’m sure the people who do like this dark, edgy stuff weren’t looking at the inconsistencies I talk about, right? They were just like, “oh man, that was so dark and edgy,” and that’s what they cared about.

Bunny: There is a way for you to have a dark, edgy character, and still employ Chris’s little tricks to make them seem less so, which is, they used to be an assassin, but now they have to do one more job and it’s justified. And this is the tactic employed by both Jason Bourne and John Wick, who are both people who used to be assassins. John Wick got out of it. Jason Bourne lost his memory.

Chris: I thought John Wick was getting revenge for his dog.

Bunny: So John Wick, he was an assassin, an incredibly effective one. Then he met his wife and he was like, I want outta this. The guy he was working for gave him an impossible job and he pulled it off and he quit the assassin rat race and lived with his wife, and then his wife died. And then mob boss guy’s son, not knowing who he was, came in, destroyed his car, killed his dog, and essentially stole everything from him.

Chris: So did he just run into the son by coincidence?

Oren: Yeah, you know, small town.

Chris: How did the son also end up destroying his stuff and not know who he was? Okay, just coincidence.

Bunny: I think it is. Like, they run into each other at a gas station and the son ogles his car and makes threatening remarks and then later comes and steals the car. In the process he beats up John Wick and the dog. Don’t watch the first part of that movie if you don’t wanna see the dog die. It’s quite sad. But he does get another dog at the end.

Oren: With John Wick, whatever his assassin stuff is is so far in the backstory that no one cares. If you wanna think about it objectively, yeah, I guess John Wick’s not a good person, but does that matter at all when you’re watching the movie? No.

Bunny: You know, the handwave trick that Chris was talking about is, don’t show it on screen. And you know, we’re meant to understand that John Wick has reformed, he’s sucked back into it. And that’s kind of the conflict of the movies is like, I mean, in the first movie, people are literally constantly asking him, “are you back?” And it’s a big snapping point when he is like, “yeah, I’m back.” And like kicks the crap out of a bunch of guys. I will say John Wick is also really refreshing in that it doesn’t do the thing where he spares the villain. John Wick kills lots and lots of people and it’s very cinematic. This is a very well done movie. Just look at that! Like, no shaky cam, it’s incredible. When he finally reaches the villain kid, you know, he just walks up to him and shoots him and that’s that. Which is refreshing.

Oren: Rude of you to personally call out Arrow like that.

Bunny: Jason Bourne does something similar. He used to be an assassin for the government, and then he was given a job where he would’ve had to murder someone in front of his children – the target’s children, I should say – couldn’t do it, and then jumped off a boat and lost his memory, and so it’s mystery/thriller. Again, the genre shifts.

Oren: And you could say he was Bourne again.

Bunny: You could say that.

Oren: My favorite one of these is actually The Black Company because everyone talks about how The Black Company is so dark and gray and doesn’t conform to your goody-two-shoes storytelling morality. But it’s very funny because they only ever fight people who are worse than them. It’s just really obvious that it’s doing the same thing any story would do. It just has a coat of grit attached to it.

Chris: Not your grandmother’s mercenary story.

Oren: It’s not a bad story, it’s just not any more morally complex than Lord of the Rings. It just has a different filter over the lens is all.

Chris: I tried to think of stories with mercenaries and I came up surprisingly blank.

Oren: There aren’t that many. You could argue that the Firefly characters act as mercenaries sometimes, but they aren’t like a mercenary company, right? That’s not their job.

Chris: They do the train job and then don’t go through with it.

Oren: They protect the sex workers in the second to last episode, you know, there are a few times where they act as hired muscle. 

Bunny: Isn’t Viv from Legends and Lattes formerly a mercenary? We see her do like one mercenary thing at the beginning of that book.

Chris: Well, she’s an adventurer, so you’d have to know, what does a D&D party typically do in that setting? They run into dungeons and fight monsters…? I’m sure the treasure there doesn’t actually belong to any goblin families. Nice goblin families that they’ve massacred.

Oren: It’s okay. Those were bad goblins, not like good goblins. If the author decides to embrace goblincore at some point.

Bunny: The other very straightforward way to make a pirate character work is just make it publicity. They didn’t actually do the bad things. They’re just very threatening because of publicity. Dread Pirate Roberts, pretty much.

Chris: Well, Dread Pirate Roberts is a pirate. They just pass the name to the next pirate. 

Bunny: Right. But people are mostly scared of him because of the name.

Chris: That’s true.

Bunny: There’s also Captain Shakespeare in Stardust, which is much more explicit.

Chris: Yeah, no, actually that one’s really interesting because they wanted to have pirates, but they’re not actually pirates. They collect lightning from the sky. They’re lightning harvesters. 

Oren: If we’re talking historically, pirates did prefer for you to surrender without fighting, so you can have pirates do that in your story. It’s just that it’s extremely unlikely that will happen all of the time.

Bunny: It would also be not so exciting.

Oren: That’s why you gotta finagle it. All right. I think we can now do the morally gray task of ending the podcast.

Chris: And if you want to protect us from any more assassination attempts that may or may not come from one of our own hosts, consider supporting us on Patreon. Go to patreon.com/mythcreants.

Oren: And before we go, I wanna thank a couple of our existing patrons. First, there’s Ayman Jaber. He’s an urban fantasy writer and a connoisseur of Marvel. Then there’s Kathy Ferguson, who’s a professor of Political Theory in Star Trek. We will talk to you next week. 

Chris: This has been the Mythcreant Podcast. Opening/closing theme: “The Princess who Saved Herself” by Jonathan Coulton.