Charlatan Background 5e Guide: Who Wants to be a Fantasy Grifter?

Last Updated on January 22, 2023

The con is on. If you love heist movies, crime capers, or just love the idea of pulling one over on an unsuspecting rube, the Charlatan background is 100% the one for you. Trust me, I’m a professional. 

Hey, unrelated, but do you want to buy some healing potions? I know they smell a bit funny but that’s just the patented toxin neutralizers. I can give you a good price but you gotta buy them all now. 

“Let’s sort the buyers from the spyers, the needy from the greedy, and those who trust me from the ones who don’t” – Bacon, Lock Stock and Two Smoking Barrels (1998)

It’s tough out there. Pretty early in life you realized honest work was a much less efficient way of making a living than separating people from their own hard-earned gold.

Violence is overrated, as is all that climbing and safe-cracking malarkey that thieves take so much pride in. 

Say the right things in the right tone of voice to the right person, and they won’t just hand over your gold, they’ll thank you for the privilege. 

You’ve always had a knack for this sort of work. You know what makes people tick, what they want, what they fear. And you know how to push those buttons. You could have gone into politics, but somehow this feels less dirty. 

With a few leading questions, a compliment that sounds oh so sincere, most folk become putty in your hands. You know just what they want and you deliver it – at least, you take payment up front with the promise to deliver very, very soon.

Your marks really should know better; what you’re saying is just too good to be true, but you’ve cultivated a talent for making people believe in little miracles. 

Whether you’re fencing stolen artwork on street corners, selling “cure-alls” made from beeswax and a dash of lavender oil, shooting craps with loaded dice, or swindling lonely old lords out of their sizable inheritances, the Charlatan is ripe with opportunities for fun roleplaying and maybe the payday of your life.  

Favorite Schemes 

Every trickster, grifter, and streetwise hustler has their favorite con, and you’re no exception. When you choose this background, you get to pick your character’s favorite scheme, the one you return to time and again as a surefire way to put gold in your purse and food on the table. 

You can choose from (or roll a d6 on) the table below. Personally, I’m a big fan of the Fiddle Game – which you could definitely pull off with a fake magic sword to great effect. 

d6	Favorite Schemes
1	I cheat at games of chance.
2	I shave coins or forge documents.
3	I insinuate myself into people’s lives to prey on their weakness and secure their fortunes.
4	I put on new identities like clothes.
5	I run sleight-of-hand cons on street corners.
6	I convince people that worthless junk is worth their hard-earned money.

Suggested Characteristics

When it comes to roleplaying your charlatan, you’ve got a wealth of films, shows, books, and games to draw from. 

You could be a flamboyant trickster who insinuates themself into high society like Jay Gatsby, a debonair con man like Tom Ripley, a career criminal like Danny Ocean, or a streetwise kid who picked up grifting to survive. 

Choose a Personality Trait, an Ideal, a Bond, and a Flaw from the list below or invest your own. 

d8	Personality Trait
1	I fall in and out of love easily, and am always pursuing someone.
2	I have a joke for every occasion, especially occasions where humor is inappropriate.
3	Flattery is my preferred trick for getting what I want.
4	I’m a born gambler who can’t resist taking a risk for a potential payoff.
5	I lie about almost everything, even when there’s no good reason to.
6	Sarcasm and insults are my weapons of choice.
7	I keep multiple holy symbols on me and invoke whatever deity might come in useful at any given moment.
8	I pocket anything I see that might have some value.

d6	Ideal
1	Independence. I am a free spirit—no one tells me what to do. (Chaotic)
2	Fairness. I never target people who can’t afford to lose a few coins. (Lawful)
3	Charity. I distribute the money I acquire to the people who really need it. (Good)
4	Creativity. I never run the same con twice. (Chaotic)
5	Friendship. Material goods come and go. Bonds of friendship last forever. (Good)
6	Aspiration. I’m determined to make something of myself. (Any)

d6	Bond
1	I fleeced the wrong person and must work to ensure that this individual never crosses paths with me or those I care about.
2	I owe everything to my mentor—a horrible person who’s probably rotting in jail somewhere.
3	Somewhere out there, I have a child who doesn’t know me. I’m making the world better for him or her.
4	I come from a noble family, and one day I’ll reclaim my lands and title from those who stole them from me.
5	A powerful person killed someone I love. Some day soon, I’ll have my revenge.
6	I swindled and ruined a person who didn’t deserve it. I seek to atone for my misdeeds but might never be able to forgive myself.

d6	Flaw
1	I can’t resist a pretty face.
2	I’m always in debt. I spend my ill-gotten gains on decadent luxuries faster than I bring them in…
3	I’m convinced that no one could ever fool me the way I fool others.
4	I’m too greedy for my own good. I can’t resist taking a risk if there’s money involved.
5	I can’t resist swindling people who are more powerful than me.
6	I hate to admit it and will hate myself for it, but I’ll run and preserve my own hide if the going gets tough.

You could even run a short campaign with a whole party full of charlatans planning the ultimate con – although you’re obviously also going to need a safe cracker (Thief, Criminal background), an acrobat (Monk, Athlete background), the brains (Divination Wizard, Investigator background), and a demolitions expert (Artillerist Artificer… any background).