D&D Classing It Up: Rogue

Back to the drawing board with Rogues — today we’re talking about how to play a rogue and be a classy one in Dungeons & Dragons. Most of the time, people play one of two types of Rogues — first is the assassin rogue. You’re super sneaky; you can hide, jump out, and deal a ton of damage and go back into hiding if somehow your one hit didn’t kill the NPC you were trying to kill. The other is the thief. You enjoy stealing stuff, even from your own party, and you are really greedy.

Image Source: Wizards

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(?)

Image Source: D&D Beyond

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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