The criminal background is one that in a game where you want to be the heroes, needs to be worked with carefully. There’s a thin line between being a hero and being a villain. In the Curse of Strahd game that I’m running, they were in a shop, the rogue character (don’t even think with criminal background) steals something, gets caught because they rolled a bad stealth check. Happened again when the rogue tried to flirt their way into getting a free drink from the married bartender who’s wife then promptly kicked that character out again.

When thinking about playing someone whose background is criminal, think about how you can play into the trope in some ways, but also it might be more interesting to play against type. In the case of the rogue in Curse of Strahd, hopefully she’ll start playing against type so that her character then realizes that they kind of suck as a criminal and reform their ways. Think about a criminal as someone who has come from a past of crime and is now an adventurer. What changed for them, are they still indebted to anyone, are they still an active criminal? There are a lot of ways that you can go beyond, I just like the looks of shiny things so I take them.

Now, I’ve just given the example of the thief criminal, but that might not be your thing. Maybe you don’t ever steal anything, but you’ve been a smuggler for a little while and you get caught up having to rescue a princess from a man in a black suit who then turns out to be her father. I might have heard that one from somewhere else. You can also a be a blackmailer or an enforcer for the local thieves guild. These probably set-up more interesting stories a lot of the time than the standard burglar who steals rings off of rich women in town because the rings are shiny.

I love nature and I knew that when I grew up, I wanted to protect nature. However, that wasn’t making a lot of money for me. People don’t pay you money when you save the rabbit caught in a snare from certain death, and they think that you’re driving off the goblins in the woods so that they are safe (still won’t pay you), not so that there are fewer creatures trying to kill the deer. One day, there was a band of brigands who came into the woods. They injured an owlbear and placed it into a cage. I could see it was gravely wounded and I went to release it and help it. I’m not that sneaky, however, and they caught me, but not until I had bandaged up the owlbears wound.  They kept  me around to keep the owlbear alive for the collector whom they had captured it for. They saw the work I had done and offered me a choice, keep helping them smuggle animals and keep them alive or they’d kill me. I knew that they wouldn’t stop smuggling animals if I was dead, so I agreed to help. It wasn’t until they got in over their head fighting a roc that I was able to make my escape, and that was a decade later. Now I’m going to get revenge on that collector and release his collection back into the wild where they belong, but I need some help doing that.

Class: Druid
Alignment: Neutral Good

It’s a silly life, but it pays way better than you’d think. That’s what I told my friends when they wondered how I lived so well, while I was a hairdresser. I have the gift of gab, and the court ladies love to have their friends over and talk, and I talk with them, but mainly I listen and I remember. I’m just the hairdresser, why would they be worried about little old me. You wouldn’t believe the gossip and rumors and scandals that you hear about as a hairdresser, but  I’ve found that it’s good to believe and remember them. When you know something really juicy, you can get a lot of money. The wife whose husbands position will be ruined if the king found out that he was fixing horse races, including the one at the royal tournament. They won good money from that, and I got good money from them. They tell you to quit when you’re ahead, but this seemed like the perfect con. An anonymous source threatened to ruin them, they paid that anonymous source money, and I kept cutting their hair. Then, whoops, my gift of gab got me in trouble with a duchess, accidentally spilled a detail that she really didn’t need to know. Now, it’s off with my head, if they can catch me.

Class: Bard
Alignment: Chaotic Neutral/Evil
This maybe should be an alignment that’s chaotic evil. It’s a little bit Loki like in just being someone who is out for a good time and doesn’t really care about others. However, if you run this as the characters only scam/criminal activity and they are doing it because it fell into their laps, it could be chaotic neutral.

I’m the wheel man. When there’s something shady going down in town and they need a fast and effective getaway, they call me. My rules are simple, no kidnappings, no killing, no stealing from those in need. If you meet those requirements, I’ll deal with you. I guarantee that you will get away, if not, it’s going to be my head on the block too. One night, I’m doing my job, waiting along a side hill, just out of sight from the mayors house. I hear some screaming up at the house, guess that someone caught them and they would be booking it back to me. Sure enough, five minutes later, the two toughs who hired me came crashing through the woods, though, I knew this was different than normal. In my torch light, I could see that one had their sword drawn, and there was blood on it and on them. I didn’t bother waiting for them, that’s my rule, no killing. I road down the one guy who was injured and shouted a warning what I would do to the other if he told on me. Turns out, he was more scared of his boss than he was of me, if I’d known who his boss had been from the start, I wouldn’t have taken the job. I heard within hours, he squealed to the cops and not only that, but a crime boss from the big city was coming out to our little town. I booked it and now I’m on the run. I hope with my mask that I’ll have remained an unknown and harder to stop, especially traveling with these goody two shoes

Class: Fighter (they commonly get access to steeds that would make them a solid option)
Alignment: Lawful Evil
I’ve said that I try and avoid the evil alignments because if you’re running a campaign with a bunch of heroes and one person is evil, it can make it tough. However, I think this offers an interesting role playing option for someone who is p laying this background. This character is clearly evil and clearly has well defined rules, if you’re up for it as a player, make this your characters redemption story. Slowly change them from evil into a lawful neutral so that instead of just being worried about their own skin, that now they are worried about more and have put their past behind them. It could offer some really awesome role playing moments if you get into it.

As a kid, my parents and everyone in my town was afraid of me. That was fine with me, I liked being on my own. I was playing in the woods one day by myself, creeping along following some of the hunters who were in the woods when I realized I’d picked up my own tail. There were some bad men following the hunters and I decided to get the drop on them. It was easier than I thought to kill a man, but that made people in town even more afraid of me. They sent me off to the temples, hoping that one of them would be able to fix me. Then I found the temple of the Raven Queen. Her priestesses told me of how there were those who had lived past their time and who needed to die. They were bad people who had made unholy deals to stay alive, and they needed someone on their payroll to take out these men. I became their hired killer and I was good at it, until I ran across the one who they only called the ancient one. None of their other hired killers had managed to get the ancient one, and I thought I could do it. I quickly realized that I couldn’t and I ran away, now I’m trying to find those who can help me take care of the ancient one before I return to the temple of the Raven Queen.

Class: Paladin
Alignment: Lawful Neutral
Just a little bit of information, the Raven Queen is the Goddess of death, and sees death as a natural thing. She really frowns upon it when those who should be dead aren’t dead because of some nefarious means in this example, and because of that, she’d be sending out someone who isn’t evil to do this work.

Have you played someone with a criminal background before? What are some interesting twists on the criminal background to make a more fully developed character than someone who is just greedy and wants to steal shiny things?

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I’m here to tell you that those are two awesome tropes (though don’t steal from your party), but there are a lot of other options for the rogue. The rogue is a skill monkey — you have more skills to start out with than other classes, and you get more expertise, which means you are really, really good at some things. So, while you can make it so you are really, really good at being a thief, you can also be a rogue who is better at many things. Leaning into a background, you can use your skills to be the face of the party, or to be a con man. You could be one of the smartest rogues out there who is sneaking into places to acquire more knowledge.

Mechanically, you’re going to end up being sneaky and focused on dexterity. This is because you have your sneak attack, which you get when you have advantage on your attacks or are attacking someone who is engaged in combat already. This allows you to dish out a lot of damage once per turn, even more so if you are an assassin-type rogue. Other than that, you really are the skill monkey who can become an expert at something. A word of caution with being a skill monkey — try to pick something that the rest of the party doesn’t have. Being good at stealth is great and probably can overlap with others’ skills, but if you have a monk in the party who is really good at sneaking as well or is good at deception, don’t step on their toes. Since you can pick most any skill, it’s better to just pick a different one. Rogue is generally the class that people go with when they want to be Batman, because you can kind of be Batman if you want to.

So what are some backstories you can go with?

Growing up on the street was tough; you had to lie and steal for a living. One day, you stole from someone and suddenly found yourself under the eyes of the local thieves’ guild. This was actually pretty great, because soon you were working with a crew, and you knew more people. Things were going well until something seemed to take over the leader of the thieves’ guild. They changed, and you don’t know how or why. Your missions started to become weird, and you stopped making money like you had been before. More and more members of the thieves’ guild changed as well. You need to find help outside the guild to figure out what is going on and save your city before the guild destroys it.

Background: Urchin (or Guild Artisan)
Class Archetype: Thief

You grew up in a small shipping town. It was a nice little town and grew larger as the town became a bigger shipping port. That attracted some unsavory sorts, including pirates. One day, the town were raided — most people hid, but you were working at the warehouse and weren’t able to get away. The pirates shanghaied you. The first few years on the ship were horrible — you got all the jobs no one wanted. But as time when on and pirates left or were killed, you got more and more responsibility. After five years, you were one of the top pirates on the ship. The captain got sick one day and passed away shortly thereafter. There was infighting among the pirates about who was going to take over, but you didn’t take part, because you knew where the captain’s secret stash was. Now you need help getting to it, but if you can, you’ll be rich, and you’ll be able to get your own ship and crew.

Class Archetype: Swashbuckler
Background: Folk Hero(?)

Your family was always a family of thieves. You’d travel from town to town, scamming people out of their hard-earned money. You didn’t do it to people who didn’t have much money to start out with — only to the rich. That gave you enough to live on. One night, a scam went wrong, and you got separated from your family. You were caught by the noble lady you and your family were trying to scam. You were still young, so she took pity on you. Instead of throwing you in jail or having you killed for trying to scam her, she offered you a position. Instead of being a thief, you were going to help protect her against any other thieves and con artists that might show up. It was a great job, and you left your life of crime behind, until someone stole the lady’s jewels and left two pieces among your belongings. Now you’re on the run, and you need to find out who framed you, which is probably something you can’t do on your own.

Background: Criminal
Class Archetype: Inquisitive

The noble of your town was not a good person, and they have a personal vendetta against your family. You were part of the highest-born family other than theirs, and they were constantly paranoid about your father stealing their title. Your father was never interested in that, but when you left to go to university, you got news that your parents had been killed in a “hunting accident.” You knew that wasn’t the case, and you spent some time in college studying so that you’d be able to take over your town and get revenge. While studying, you spent plenty of time also learning how to use weapons and to be able to kill without being seen. When you become a noble, you can hire someone to kill for you, but until then, and with the noble of your town, you want the revenge yourself. But to get in and kill them, you’re going to need help.

Background: Sage
Class Archetype: Assassin

When playing a rogue, have you stolen from your party? What have been some of your favorite rogue moments?

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