D&D Backgrounds: Entertainer

Sorry for the slow week of posting last week, I’m getting into a new schedule at a new job and figuring out when and where I have time to work on the blog. I’ll be back to a more regular schedule probably next week when I start going into the office earlier so that I have more afternoon/early evening free. But I wanted to get a post up today about the Entertainer background in Dungeons and Dragons.

Image Source: Wizards

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.

Image Source: D&D Beyond

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.

Image Source: Wizards

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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