Fantasy Grifters: Charlatan 5e DND Background Guide

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Want to play a fantasy grifter? I’ve got some charlatan 5e DND backgrounds you can use for your thief character.

Do you want to play a Thief who has tricks up his sleeves? A grifter, a scam artist, a thief who pulls a fast one on you!

The above is a quick rundown of the charlatan background for thief characters in DND 5e. Let’s take a deeper look.

Charlatan 5e DND Background Guide

Here’s a bunch of information on playing a charlatan thief in DND 5e.

Charlatan Favorite Schemes

Choose a favored scheme that your character uses.

  1. Card Cheat – You have a deck of marked cards that you have taught yourself to read quickly and accurately. You can use this in combination with your other abilities.
  2. Disguise – You are an expert in disguise.
  3. Con Artist – You can trick people into making a deal with you. You can subtly change the terms to better suit you.
  4. Street Performer – You are a skilled performer, possibly a magician or an acrobat. You find that your little tricks can convince rather than actually be difficult.
  5. Gambling House – You work for a gambling house or a card shark or an ally of them. They send you out to secure money from people.
  6. Street hustler – You are a master at the hustle. You sell goods of questionable quality to unsuspecting victims.

Personality Trait:

Here’s some options for a charlatan personality trait to use. You can choose other personality traits if you want.

  1. Friendly and charming, they love to tell a good story and can con people with their words.
  2. You love to take risks and will take any opportunity to do so.
  3. You are frugal with money and don’t spend it on frivolous things.
  4. You’re good at reading people and telling if they’re lying.
  5. You are very superstitious, believing in omens, signs and signals.
  6. You are a quick thinker, who thinks on their feet.
  7. You love money and want to make a profit at any cost.
  8. You’re very good at telling the truth.
  9. You are a gambler and like the thrill of the win.
  10. You like to save money.
  11. You like the thrill of danger.
  12. You are a sucker for an honest man.
  13. You love to brag about your own stories.
  14. You’re good at reading people and know if they’re lying.
  15. You are good at deceiving people with your words.
  16. You like to drink and party.
  17. You are superstitious, believing in omens, signs and signals.
  18. You distrust the nobility and their power.
  19. You love to gamble.
  20. You enjoy telling the truth.

Charlatan Ideals

While you’re a thief, you have some ideals as a charlatan.

  1. Don’t take advantage of the poor.
  2. Don’t take advantage of people who are foolish.
  3. Don’t take advantage of people who are drunk.
  4. Don’t take advantage of your friends.
  5. Don’t take advantage of children.
  6. Don’t cheat people for no reason.
  7. Don’t cheat people who can’t afford it.
  8. Don’t cheat people who are too drunk to realize.
  9. Don’t take advantage of the inlaws.
  10. Don’t take advantage of the noble.
  11. Don’t take advantage of the clergyman.
  12. Don’t take advantage of the innocent.
  13. Don’t take advantage of the stupid.
  14. Don’t take advantage of the dead.
  15. Don’t scam people in your own area.
  16. Don’t scam people who are too far away.
  17. Don’t scam people who are more powerful than you.
  18. Don’t scam children.
  19. Don’t scam women.
  20. Don’t rob people named Rob.

Charlatan Flaws

Here’s some flaws for a charlatan 5e DND background.

  1. You are lazy. You don’t know how to do things yourself. You’re a helper, not a doer.
  2. You’re addicted to gambling, drink or drugs.
  3. You’re very superstitious and afraid of omens, signs and signals.
  4. You’re very greedy and want more money.
  5. You’re very trusting and willing to do anything for anyone.
  6. You believe in omens, signs and signals.
  7. You are afraid of power and are wary of the nobility.
  8. You like to spend money before you make it.
  9. You’re very paranoid and suspicious.
  10. You’re a cheapskate and won’t pay your debts.

Skill Proficiencies

Deception, Sleight of Hand (or other skill proficiencies as your D&D DM sees fit…)

Tool Proficiencies

Disguise kit, forgery kit

Charlatan Equipment: 

A set of good clothes, a disguise kit, and a pouch containing 1d20+10 gp, forgery kit

Languages:

No extra languages.

Charlatan Backstory Examples for DND 5e

1) Born to a Beggar – Born in the streets to a gifted beggar, you grew up learning how to pull heart strings – and purse strings too. Over the years, your father taught you all of his tricks – from how to falsify wounds to how to manipulate money out of the pockets of passersby. You cannot resist taking a risk.

2) The In-Law’s Delight – You are the son and heir of a member of the nobility. You never really learned how to be a thief, but you did learn how to take advantage of your father’s status. You are a master at using the in-laws to get exactly what you want.

3) The Street Performer – You grew up in a poor family. Your father was a street performer. He was good at telling stories, but terrible at telling the truth. You learned how to perform for an audience and earn money that way. It’s how you bought your first disguise kit.

4) The Promising Apprentice – You were the daughter of a famous and skilled grifter. Your mother taught you everything she knew and you were her best apprentice. However, you decided to go out on your own and start your own con game.

5) The Young Con Artist – You were always a natural con artist and hustler. You never knew your father and your mother always promised that he would be back and that you would have a better life. But she was forever lying as well, so you never knew if your father would ever come back. So, you decided to go out on your own and start your own con game.

6) The Street Scambler – You grew up on the streets. You learned to be a street performer and a street grifter. You’ve scampered up some of the most powerful people in the city. So, you decided to take your skills to the next level and start your own con game. Your belt pouch is full of your earnings, including a signet ring worth more than its weight in gold.

7) The Young Grifter – You grew up in a grifter family. You learned how to manipulate people and get your way ever since you were a child. No one can tell you no and if they try, you’re very good at manipulating them into saying yes. But now you’re going out on your own and starting your own con game. With a set of fine clothes and a smile, you’re on your way.

8) The Gambling House Kid – You worked for a gambling house or a card shark or an ally of them. They sent you out to secure money from people. You never really knew why they did it, but they did it to help their own ends. You were a street grifter, just like your father, and you cannot resist taking a risk if it will make you wealthier.

9) The Street Singer – You grew up in a poor family. Your parents were street performers. Your father was a street performer and your mother was a street singer. You learned how to perform for an audience and earn money from them.

10) Shadow of the Alleys – You grew up on the streets. What you lacked in wealth, you made up for in street smarts. You could sniff out a scam a mile away and you knew how to stay out of trouble. You were a street grifter, just like your father. You were good at deceiving people with your words. You find it hard to resist taking a risk to increase your riches.

Playing a Charlatan Thief Character in DND 5e

A grifter is a roguish character class and should be treated as such. At 1st level, you get to choose two skills that you are naturally good at. This can help flesh out your charlatan background.

Paul Bellow

LitRPG Author Paul Bellow

Paul Bellow is a LitRPG author, gamer, RPG game developer, and publisher of several online communities. In other words, an old school webmaster. He also developed and runs LitRPG Adventures, a set of advanced RPG generators powered by GPT-3 AI. Here at LitRPG Reads, he publishes articles about LitRPG books, tabletop RPG books, and all sorts of DND content that's free to use in your personal tabletop campaign - i.e. non-commercial use. Enjoy your stay and reach out on Twitter or Discord if you want to make contact.