How to roleplay a rogue in D&D

How to roleplay a rogue in D&D

The best way how to roleplay a rogue in D&D is not by being the loaner. Being a loaner is an option and you can do it well, but there are many other ways to play a rogue.

How to roleplay a rogue in D&D depends on what your rogue does and who they are. Rogues are varied, so your playstyle will change how you roleplay.

Every rogue has a different way to play. There are faces, thieves, assassins, treasure divers, black market dealers, and the list goes on. You have to first figure out what way you are going to play before you decide on how to roleplay a rogue in D&D.

The wrong way to play

“Travis sat in a corner. It was the shadiest corner in the inn. He waited patiently for people to talk to him because who could resist a lone, brooding man? No one! So there he sat until the party approached him. That is when he showed them his dark. His standoffishness. The side, of EDGE!”

Paladins and bards have a stereotype. We have covered them in the past. The paladin here and the bard here. But even they do not come close to the stereotype of the rogue. The paladin and the rogue do have something in common. Each archetype is different and completely changes how you will roleplay your character, so we will look at almost all the archetypes like we did with the paladin.

How to roleplay a rogue in D&D is NOT by being a loner. You can be a loner, but that is not just who you are. You have done some shady things to be where you are, but that is not who you are. These are a part of you, but not the whole package.

This is what many rogues seem to forget. How they became a rogue is not all there is. It is an influence, but it is not everything!

I have to repeat this because there is not really a wrong way to roleplay most characters. At least, not 1 stereotypical wrong way. For the rogue there is, and here is why.

When you are the sweet lord of EDGE you are not interesting. People don’t want to come to you and beg for your attention. They will be bored, put off, and annoyed by it at best.

Being a loner can be interesting, but it is hard to make interesting. You are part of a group. You have all decided to play adventurers and work together. If a person makes a character who doesn’t want to be an adventurer then the game doesn’t really work for that person. The same goes for a person who doesn’t want to work with the group.

The nature of a rogue means that they most likely will be alright being alone. It just comes with the territory of stealth, traps, etc. That does not mean that you have to prefer to be alone. This makes you isolated from the group and becomes a problem quickly. Dissension can be sown and the game can lose it’s luster for players quickly.

This is why we are covering how not to play the rogue first. The stereotype is an annoying rogue who will only cause problems in your game, and will probably try to take the spotlight from other players to focus it on him/herself.

Now that we have covered how NOT to roleplay a rogue in D&D, let’s look into some ways how to roleplay a rogue in D&D.

The thief

The most common way how to roleplay a rogue in D&D is by making them a thief. This is the classical version of the rogue. A rogue is there to take care of traps, get loot, pick pockets, and be involved in crime.

Roleplaying a thief might seem stereotypical at first, but you can roleplay a thief completely differently each time.

First, ask yourself why your character is a thief? Is it because they grew up as an orphan and had to steal in order to survive? If so, how did that affect their outlook on life? Is it bleak or are they always trying to find the silver lining in order to not fall into despair?

Instead of growing up on the streets you could have lost everything and been forced into crime. If you weren’t forced into crime, why did you decide to become a thief? Furthermore, what if you are a legal thief? An adventurer for hire in order to get treasure like a tomb raider.

Did you get training because of your circumstances or did you seek out training in order to do what you wanted?

These are all questions that can help shape your character’s outlook on life and how to roleplay a rogue in D&D.

Being a thief helps you figure out your outlook on life and how to roleplay from there, but there are other ways of roleplaying a rogue.

The assassin

Not all rogues are thieves. Rogues are characters who fight with underhanded means in order to win. Stealth is not a ‘fair’ assessment of combat ability, but you don’t care. As long as your knife finds the target’s throat you are fine with the outcome.

Most thieves in the underground just want money. They do not want to kill their clients because that would mean the thief loses a source of income. They want to maintain the money and will figure out how to do so, but you don’t care about that. You are the knife in the night that wants to kill instead of just taking some money.

The assassin is an interesting way on how to roleplay a rogue in D&D. On 1 hand, the classical idea is that an assassin was evil. You are after all paid to kill people. That is pretty dark. But isn’t the rest of the world? Adventurers kill monsters and in order to take items from that monster’s home. Even if the monster has intelligence that is fine but hired murder isn’t?

This is a question you can use to develop your character. Killing for a living is already a grim task, but your outlook on it can shape your character. If you just kill for money and don’t ask questions it leaves your character a little hollow.

You need to dig deep and figure out why your character is alright with killing people, and even more so why you chose this line of work. If you chose to be an assassin for adventuring purposes, why chose an assassin instead of a normal fighter?

You could have chosen to learn about weaponry and be an asset to your team that way, but instead, you chose to be an assassin. Did you want to end a fight before it began? Make the combat end before it began, or was there another purpose to training in the silent arts of murder?

As you can see, the lone gruff hired hand to kill isn’t the only way to play an assassin. You even with an almost exclusive subclass are able to mold it into whatever you want. Roleplay should be easy for you, just please don’t pick a boring character cut out of a lone hired hand with no personality.

There are many different ways to roleplay a rogue in D&D, and each subclass offers its own unique way to play a rogue.

The charmer

You can technically be a charmer with any subclass, but the swashbuckler is best suited for this. Rogues are not great in a fair fight. They 1 on 1 cannot compete fairly with a fighter. That is why the swashbuckler isn’t a strong fighter. Instead, they are a charming face that will win in an underhanded way.

You fight dirty and get into another person’s head mentally. This is rare for a rogue, but everything about how this subclass plays is dirty.

When you have such a charismatic character you tend to stand out. That means you cannot just be a brooding loner who hides in a corner. You are a charmer, a swindler, and someone will promise marriage but then run off.

In order to do this, you need to have a bright outlook on life and ask yourself a few questions.

  • Why are you okay with dirty combat?
  • Why do you appear charming even if you are a snake?
  • Why do you like to deceive people?
  • What made you decide to live this type of life?

Once you answer those 4 questions your swashbuckler will become a bit deeper than the normal ones out there.

While it is nice to have a good face, that is not the only way how to roleplay a rogue in D&D.


Instead of having a pretty face you have a sharp mind. These characters are usually able to become villains in their own settings, but you can play them differently.

If you are a good rogue, you could end up being more like sherlock holmes who solves mysteries. Rogues are at their core someone who plays dirty to get what they want and do not really care about the law. While playing a rogue who cares about the law would be interesting, you most likely will not and might even go against the law to help others.

That is right! I am talking about becoming Robin Hood. Did you think he was a ranger or a fighter? Be real with yourself! Robin Hood strikes from the shadows, never fights fair, and has no respect for the law. You can do the same and steal from the rich, sabotage the government, do whatever you want in order to help people.

On the other hand, you could always be plotting something. Something big!

You might even think that you can run the city better than the government can, so you start bribing people and making them do your bidding. This also fits into the other aspect that rogues are usually associated with.

The spy

Every rogue at 1 point in their career is a spy. It could be that you are spying on the enemies to gather information for your party. Other times you could be the spy who is sent to find and possibly disarm traps. Making your career that of a spy is something completely different though.

The mastermind, scout, and inquisitive subclasses are all great choices for being a spy. You might be a spy in the wilderness and rely on stealth/underhanded tactics to get out of a bind and report back what you learned.

As an inquisitive, you are very perceptive and able to figure out things that others want to stay hidden. This could be a great quality to have as a spy, and the mastermind will just outthink their opponents.

These all make sense, but how should you roleplay your character as a spy?

Being a complete loner is not a great way to roleplay a spy. It makes sense, but you are supposed to gather information and report it back. What about the people who you report to? How is your relationship with them? Do you like being alone or do you want to be with company?

Think also about how being a spy affects you. Are you a nice trusting person? Most likely not. Your job is to be unseen, lie, and get information that others do not want your allies to have. This might make you a person who is distrusting and always looking for an angle.

Instead of being a lone brooding type you can try to figure everyone out. Make your own mental or physical document of how everyone acts and why. Learn more about your party than they know about themselves. Eventually, get to the point where you say what they are thinking and creep them out. Once you do that, you know that you are playing a spy well.

But there is 1 last type of rogue that we are going to cover today.

Arcane trickster

This is possibly the weirdest way on how to roleplay a rogue in D&D. You are a rogue that tries to get what they want in an underhanded way, but yet you are using magic.

Magic isn’t too uncommon for adventurers, but you have to consider what made you take an interest in magic. Instead of being a wizard, you are a rogue so there has to be a reason why you have focused more on the roguish aspects.

If you study magic, it might not be as a legitimate wizard. You could be a smuggler of stolen goods and are always looking for new treasure and how much you can get for it like a thief.

Instead of selling magical knowledge, you could be a scholar. Not a very good scholar mind you, but someone who is interested in magic. You have in order to learn magic had to make some tough choices. Magical training might not be cheap, so you have had to do some shady things to learn about it. Your shady dealings may also be the reason why you cannot study magic respectably and are just getting by with the scraps that you can get your hands on.

Being an arcane trickster instead of a wizard allows you to have an almost unlimited number of background options that can shape how you roleplay.

Any 1 of these options will make your character fascinated about magic, but you can come up with any number of reasons why your rogue is an arcane trickster instead of a full-blown wizard.


I feel that we have barely scratched the surface on how to roleplay a rogue in D&D. Each subclass gives you a unique set of options. These options are a great guideline on how to play your class, but they have 1 thing in common.


They fight mentally, try to trick or instantly kill their opponent, and much more. How you fight is not fair and any fighter would not enjoy fighting you. You are a bag of tricks with a certain specialty, but all rogues never fight as a person expects.

As long as you keep this in mind and consider why you fight/live the way you do, you should be able to roleplay a rogue in D&D very well. Just please, do not make a loner who is the lord of edge.

Also, if you want to check out our other guides on how to roleplay different classes then check out our theory blogs here!

This has been Wizo and keep rolling!

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