Entertainer is probably one of those backgrounds that you can see going so many different directions. There are many different things you can do as an entertainer, though, music is going to be the one that people think of first with the entertainer background. The fact that you get a musical instrument that you’re proficient with makes it lean that way. As a player, I’d just look at that as optional, or that your character is proficient with the harp, and you can’t really lug one of those around, so what does it matter. Let’s jump quickly into these backstories and see what other ideas I might have for an entertainer.

The life of a dancer is all that I ever wanted. As a young age I trained under the greatest tutors that my parents could afford and I wanted for nothing. I grew up wanting for nothing and being the most graceful creature most people had ever seen. Life took a turn for me when my parents lost everything. A conman came and swindled them out of everything that they had. We were left on the streets, my fancy tutors were gone, and I had nothing. My parents couldn’t even feed us most nights. I decided to run away and found a convent that would take me in. There I was able to learn more fluidity and grace. A traveling troupe passed by there and I decided it was time to leave when I saw who the leader of the troupe was, the same man who had conned my parents. He didn’t recognize me, and I quickly ingratiated myself into the group and was performing and stealing from the rich with them. He wouldn’t have caught onto who I was and I would have had my revenge, but unknown to me, my parents had sent my youngest sibling to work at an old family friends so they could have a good life. My sibling exposed not only the conman but myself as well. He escaped, though most of his troupe didn’t and I had to run as he swore revenge on me, even though I hadn’t done anything. I’ll still get my revenge against that man who ruined my family.

Class: Monk
Alignment: Lawful Neutral
I’ve tossed around this characters idea for a while and it’s a character I’d love to play,  either as this character, or as a character who is still part of the troupe and everyone is playing as troupe members and we’re going around and conning people. It seems like a fun twist, and having an entertainer who isn’t a bard is nice.

Circus life was great as an oddity. No one ever thought I fit in, expect when I was in the circus. I was taller than most of my peers and stronger than them as well. People called me a freak in my home town, but when the circus came around, I had a chance to run away and fit in. Things were great until a horde of villagers blamed us for children going missing in the town. We had to scatter, each running in our own direction. I wasn’t able to find anyone. I might not be the smartest, but I took it upon myself to find out what was actually going on in this town, clear the circuses name, and get the circus back together. I need to find someone smarter than me though, who will have an idea of where to look, if anyone will talk with me because of how I look.

Class: Barbarian
Alignment: Neutral Good
The gentle giant type of character, has to be strong though, and probably is Dragonborn of Half-Orc as both of those would stand out from the crowd and probably freak people out.

Marvelous Magic is the name of my act. Conjuration is my favorite trick. People ooh and ah over flashy things like that, and I have plenty of gigs going around my home city.  I came here when I was young, but I already had a knack for magic and making things appear. The city was going to be the spot where I made it big, and I definitely did. I made it so big that people looked up to me, and not just that, I got a rival. That sounds cooler than it is. We were trying to one-up each other all of the time, and I was almost always ahead of them in terms of talent, but I’ve had more time to practice than they have. One day at my Marvelous Magic Shop (all about the merchandising), I got a knock at the door, which is odd, but I didn’t think much of  it, it isn’t that great a shop, maybe they hadn’t thought it was open. It was the city guard, apparently someone had stolen a broach from one of my places I often perform at, and they had a tip it might have been me. Sure enough, they found the broach in my apartment and that was enough to send me to jail for a little bit. You guys can guess how it went, my rival had set me up, I knew it, but I had no way to prove it. Now I’m disgraced and just out of jail after spending ten years in prison, do I want revenge, yes, but I want to take him down as the scum he is, and ruin his reputation, not just some petty revenge, and with the rash of thefts that have been happening at the places he’s been performing at, but not while he’s performing, I think I know how I can take him down and clear my good name.

Class: Wizard
Alignment: Lawful Neutral

The royal acting company is not an easy place to get into, and you have to be well known indeed before you can step foot on their stage. It’s even hard to get a ticket to a show, but I remember one summer when my parents and I went on our yearly trip into the big city, they surprised me for my birthday with tickets to the show. They were standing room in the back, but I have been bitten by the acting bug. One could say that it bit me a little bit too hard. I spent all my time neglecting my chores, putting on little plays with my friends. My parents liked it well enough, but those tickets had been expensive and acting lessons would be even more expensive, but it was my dream to make it onto that stage. During one of my one person shows that I put on back by the river, a man in a floppy green hat happened to see me. He applauded and asked me if I was going to be an actor, I said I was going to be the greatest one of all time. He said that he could help with that if I was willing to make a deal. I wasn’t the smartest kid, but I told him that I would as long as I would be the greatest actor of all time and perform with the royal acting company. We shook on it and that’s when I got my powers. They helped me get to that stage, and my performances were talked about as the greatest that had been seen on the stage. One evening, the man in the floppy green hat showed up and told me that it was my turn to keep my end of the bargain. Had performed on the stage and was called the greatest of all time, it was time for me to leave and help him. I had no choice, but I’ll figure out a way to break his hold on me and get back to that stage.

Class: Warlock (Fey)
Alignment: Chaotic Good

There are so many different entertainer stories that you can tell for your character and so many interesting ways to go with it. The jaded artist, the author who is looking for an adventure to write about, the bard who is collecting stories which Tate was in the first season of Dungeons and Flagons. Lean into all the weird arts as well, maybe you have a druid who is a musician but a musician as part of a drum circle that keeps a sacred grove alive. Or you have a paladin who wants to be a famous poet, but really can only write about their deity. There are lots of great entertainers waiting to take the stage of your Dungeons and Dragons game out there.

Have you played a character with an entertainer background before? What did you go with for that?

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The Players Handbook gives a number of ideas for what your charlatan could be like, they  might cheat at games of chance, be a forger, or take on new identities. There are a ton of different ways that you can go with it. It gives you some skills that you’d expect with deception and disguise, you’ve become good at those. It also gives you a second identity that you have already prepared, yes, you’re always going to have the charlatan background, and your class won’t change for it, but it provides very interesting role playing opportunities.

So, without further ado, what are some backstories?

You came from a poor family and you saw the wealth that various religions and religious officials had, and it was something that you really wanted to have yourself. So you started coming up with a con, you went to a new town, found out what temples were there, and founded a new one of your own. A little bit of flattery and you got the city lord to help you get it started. You didn’t believe in the deity at all, this was your way to have money and live a plush comfy life. Things were going great, you have people fawning over you, you had all the money and food that you’d ever want. Then one day you were sitting in the temple by yourself and you had a vision, the vision of the deity that you’d be pretending to serve. They told you that even though you hadn’t meant to do their work. But now it was time to pay back what I had taken from the poor and the needy, those who didn’t deserve to have their money taken. The deity gave me a list and told me to use my skills to pay back and spread their word across the lands.

Class: Cleric
Alignment: Chaotic Good
Just a few notes on this one, their background is chaotic good because I’m going to have them following a good deity, but because of the charlatan background they are going to be pretty chaotic. And that works, while they were scamming people they might have been neutral evil, but now as time has passed, they can easily be chaotic good having moved up on the spectrum.

I can’t resist a pretty face and a good story and good drink now that you mention it. Some would call it a flaw, but I just consider myself to be blessed with a strong appreciation for the finer things. Now, that isn’t to say that it doesn’t get me into trouble every now and again, but I can get out of trouble in a pinch. Didn’t I say I have a silver tongue before? When you accidentally sleep with the betrothed the day before their wedding, their parents get a little pissed off at you, when you accidentally sleep with the parents before the wedding, the betrothed get pissed off. But I was so charming, so what would you expect. This means I kind of have to change who I am pretty often, it’s a bit tricky, remembering where I’ve all been, what faces I’ve put on, but I’m pretty sure that I can juggle it easily enough and one of these times it will be true love. Then I found out that one of my dalliances might have led to a kid to try and keep me around, that was a big mistake. But I’m not a bad person, so I’m trying as hard as I can now to make the world a better place for them.

Class: Bard
Alignment: Chaotic Neutral
This would generally be thought of as a male character trope, but have some fun with it. It’s very possible that your character while having a fling with a bride to be talked about how she wanted to eventually settle down and have kids, and the bride to be, calls off the wedding for the character (at which point the character skips town to avoid the parents of the betrothed) and ends up getting knocked up and letting your character know that she’d started a family for them. It would be fun twist on how it normally would go.

The sound of coins clinking together is what I love, nothing makes me happier than money, at least that’s what I thought. I was one of the best as games of chance, but that was because they weren’t chance for me. Whenever I could find cards or dice, I’d hop into a game and swindle them until I’d taken just enough of their money that they wouldn’t be too mad at me. It was a solid way to make a living for myself and my younger sibling. Then I got into the game with the Count of [Insert City/Land Name] and got a lot of money from him. He was pissed off, he couldn’t prove that I cheated though. That night while resting in the tavern, I was having a drink while my younger sibling was sleeping. I go back to our room to find them dead, stabbed in their sleep with a handkerchief of the Count resting across their face. I’m not a fighter and I was scared for my own life, so I ran and hid in the woods where I met a druid who taught me skills that might help me get my revenge, now I’m ready to come back out of the woods, find some help, and get my revenge.

Class: Druid
Alignment: True Neutral

Bits and Bobs was a great shop. I’d buy people worthless junk, or even go digging through their trash, polish it up a little bit, and convince the nobles that it was going to be perfect for their sitting room. If I charged them 100x what it was worth, that’s their own fault for believing me. Plus, it gave me a great life. I spent my money faster that I made it, and soon I found myself in debt to some less than savory characters. I’m now trying to figure a way out of that debt, I’m getting close, but they keep on having me steal from people. It’s not like I’m bad at it, I’ve had experience with my scrounging before, and it was all going well. But there was this man, down on his luck,  you could easily tell it, it was his one prize possession and actually worth a chunk of money and might have gotten me out of my debt. I’m fine screwing over the rich, they don’t need all of their money, but this guy would have been out on the street if I’d taken it from him, so instead a ran. Now I have the unsavory characters after me and I need to leave town. Maybe I’ll find some other way to pay them back later.

Class: Rogue
Alignment: Lawful Neutral
I went lawful here because this character has a set of moral codes, they might not match the laws because they are willing to swindle people as long as they are rich. However, they clearly have defined who they are willing to steal from, and prior to being made to steal stuff to pay off, stealing wasn’t something that they did. They’d scrounge for stuff and maybe had a liberal opinion of what had been thrown away, but they weren’t a thief.

I was young when I found out about my powers. I didn’t know how to control them well back then, but I noticed that I had an ability that really let people open up to me. I found out all sorts of juicy gossip about my little town, and as a kid, I didn’t think anything about it, until a couple of really pissed off adults, because I told the baker’s son that his dad might actually be the blacksmith, because his mom wasn’t going there to get smithing work done for them like she claimed. That one got me in trouble, and got me run out of town. My parents stood up for me and were going to protect me. I used my ability on them to tell them that it was okay, and that I had left for a better reason. I’m not sure if it worked on them, someone will likely remind them of what I’d done, but I was on the run. My ability was useful though, stick me in front of someone who looked like they could help me for a few minutes, and I got enough information about them that I was able to play off their fears, desires, and sometimes even blackmail. I made a name for myself, not for being a sneak, because who wants to admit that I knew a dark secret about them when I could then blab that secret to anyone willing pay and listen. The only tough part for me is that I’m moving around a lot. I’ve made some great friends and that is what really matters to me, but when I find out a secret about them, I’m never sure if it’s because of my ability or because they really like me. It’s hard and I can’t stand it, so I leave. I want to know that I have a real friendship with someone some day, that’s what I really want.

Class: Sorcerer
Alignment: Chaotic Neutral

There are a number of ideas for how you can play a charlatan. The rogue class is the most obvious answer when thinking about classes, but I started with a cleric who had been a charlatan. It’s helpful to remember that this is your background, so you don’t need to lean into it too much. For one of them, I even went with the personality trait of that really suggests you steal whenever you can. So, this is one that I’d recommend being careful (as well as Criminal which will be next week), as you can end up playing against the party if you aren’t careful. But, as my examples show above, you can find ways to play a former charlatan or still an active one without being mean to your party.

Have you used the Charlatan background, what are your thoughts on it?

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The first one alphabetically is the acolyte. You’ve spent time in service to your deity. For example, maybe you started as someone who assisted the priestess as a child and then rose all the way up in the ranks to become the high priestess yourself. As I mentioned, there could be a large gap of time since the period when you were in service to your deity, but even though it could be something you did a long time before you started adventuring, it can still be a part of who you are as an adventurer. It is just a piece that has helped define who you are as a person.

There are a number of obvious classes that make the “most” sense to go with if you are an acolyte, the first being cleric. If you’re a cleric, that’s exactly what your job was in the temple that you served in, and it makes perfect sense. Next, there is paladin. This also makes a ton of sense; you are a knight in service of a deity. And then there is the monk — while the monk in Dungeons & Dragons is as much a ninja as a monk, they can make sense as an acolyte, as they trained in a monastery and have devoted their body and actions to their deity. I’m probably not going to write out much of a background for any of those classes, but I’m going to give you some weirder options or show you how you can play against type. Let’s see what some of those look like now:

I spent so many years in service of Tymora, the goddess of good fortune, and I had worked my way up into the temple. I loved the life as I spent time drinking and eating with the rich and famous of my home city. Life was great, and I was close to becoming the high priestess in my town, until my rival, Gerhim Methezar, lied to the leaders of the religion and told them I’d been preaching lies and accepting bribes. I was branded a heretic and cast out penniless onto the streets. I hate it out here, and I hate Gerhim for what he did to me. In my weakness, a voice came to me and offered me hope, offered me power, and offered me a way to get revenge. I will prove Gerhim for the liar that he is, and regain my spot in the temple of Tymora — until then, I’m going to be a thorn in his side.

Class: Warlock
Alignment: Lawful Neutral

For this one, I really leaned into the idea of being kicked out and wanting revenge as the bond and then loving rubbing elbows with the elite as a personality trait. The ideal that I used was around wanting power in the faith, and the flaw is picking a goal and becoming obsessed with it. I’m not going to break down all of them like this, but I wanted an example of how I wrote a backstory with using specific aspects from the handbook, even though I didn’t pick them out ahead of time.

I’m also going to be adding in alignments. I doubt you’ll ever see any acolyte character be actually evil, but in this case, the character might border on lawful evil at times, especially when it comes to undermining Gerhim and gaining back their old position, because of their obsession with getting their power back.

The gods speak to me and through me. That’s how the temple of Mystra found me. They seek knowledge, and I had a knowledge that they didn’t have access to. I was raised in their temple as an oracle of the gods and never knew what real life was like. Things were great until one of my visions was wrong. I don’t know what happened — maybe we interpreted it wrong, but people lost their lives, and I do not consider that acceptable. I ran away that day, but the visions didn’t stop coming. Now I’ve had another vision, about a lost relic of Mystra. I can prove to myself that I am worthy of returning to the temple if I can find this relic and bring back a piece of lost knowledge.

Class: Wizard – Divination
Alignment: Lawful Good

Life was hard for me growing up; I was living on the streets and having to steal. I made the mistake of breaking into a temple of Bhaal. They had some very nice things in there, but they caught me. According to their beliefs, that would be enough to have me put to death, but instead, they had some pity on me — I guess it was pity, anyway — and they put me to work. Apparently, no one else had ever gotten as far into the temple as I had. I didn’t love the work they made me do; it was messy work, and as my skills were honed, the work became so violent that after one mission I didn’t feel like I could return. So I didn’t. I ran away, and now agents of Bhaal are trying to track me down. But they trained me well, and with a lot of skill and a bit of luck, I’m sure I can stay ahead of them. Time to find a crowd to blend into and pretend like I’ve had a normal life.

Class: Rogue – Assassin
Alignment: Chaotic Neutral

This is definitely one that you could go evil with — just swap it around so that the temple of Bhaal has burned your character because of some mistake done on an assassination, and now you have a character who is still on the run from them but who enjoys the killing and being a rogue if you’re playing an evil campaign.

I loved living in the church, I spent my youth at the foot of the eldest priest listening to the stories he told. I memorized every single one of them, as I asked him to tell them over and over again. When he passed away, the temple in my little town didn’t get another priest, and I wasn’t sure what to do. I took up traveling. It felt like the right thing to do — seeking out those who are part of my faith so that I can listen to their stories and add them to my knowledge, so I can spread the word to the masses who might not have heard the stories before. There’s a proverb for everything, and I know them all. Unfortunately, life on the road is a bit tougher than life in the temple, but I will not give up my mission to bring these teachings to the masses. However, after a run-in with some people who claimed to be following my deity who then robbed me, I probably should figure out a better way to travel — I’m sure there is someone out there who would let me travel with them and whom I can share my message with.

Class: Bard – Lore
Alignment: NG

How have you played an acolyte before? Is your character a strict follower of some deity, or a former disgraced member who has been kicked out?

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