Exploring the Entertainer Background

In the game of Dungeons & Dragons, a character’s background represents their upbringing and what they used to do with their life before becoming an adventurer. Every character is unique and spent their time differently before setting out to find fame and fortune slaying monsters and saving lives. This can make choosing a background difficult at times. If you are new to the game or would like to know more about how backgrounds function, you can check out my article What Is A Background & How To Use It.

What is an Entertainer?

An entertainer is someone adept at moving you through the art of performance. These talented individuals can bring out one’s emotions through the art of song, dance, or storytelling and use their charismatic energy to make you feel anything from joy to sadness or outright anger. Despite the medium they choose, or the feelings they want you to feel, they only have one goal, to make sure every performance leaves you asking, are you not entertained?


Entertainers in D&D

The entertainer background is very commonly used among, you guessed it, bards. Just because that is a natural fit for a bard, it doesn’t mean they are the only ones to have lived their lives performing for others. Anyone can turn a skill into entertainment for others which can lead to some unique performances. The unlikeliest talent can be turned into a captivating show that’s difficult for one to forget. Or you could be good at cracking jokes and being the class clown, which is just fine too.

Entertainers use a wide variety of interesting skills to put on a memorable show. A gladiator is just as much an entertainer as any musician or actress, they just use their talents in fighting and acrobatics in their performance instead of words or song. Someone in the circus can use their skills in Acrobatics or Sleight of Hand to become a nimble rogue, or a cleric could use their voice to entertain their congregation through giving energetic, interactive sermons while a mage uses their skills in the arcane to wow audiences with displays of brightly colored, whimsical spells. Entertainers can usually find work in just about any city or town, and can often result in free food or lodging. Whether that be serenading townsfolk and travelers at the local inn or a troupe performing for a seedy noble with less than noble intentions, entertainers are useful to many types of folks.

Routine Entertainment

Many individuals who dedicate themselves to the performing arts generally have a variety of talents they can use to tailor their performances to meet the needs of their audience. However, each one of them has their specialty, their act that utilizes the best of their abilities to create their best show. When choosing the entertainer background this is shown by selecting your character’s entertainer routine. 

An entertainer’s routine can stem from several different activities and skills. These can include things like acting, tumbling, fire-eating, and storytelling. Entertaining a crowd can be more than just plucking a lute and singing a few verses. The Player’s Handbook offers a table of different options for your entertainer’s routine. You can select any of the options that are available for use there, or you can work with your DM to come up with a unique routine that focuses on the specific talents of your character. Just have fun with it and make it something that will be entertaining for you to play.

Entertainer Feature: By Popular Demand

With each background comes a background feature and this one comes with some nifty little perks that can be used in some interesting ways. The By Popular Demand feature allows you to be able to find work entertaining others in any town you find yourself in. Most of the time this will probably be at a tavern or inn but can be used to find work in a circus, a theater, or even a noble’s court. With your performance, you can be rewarded free food and lodging comparable to a comfortable or modest lifestyle as long as you perform each night that you wish to reap those benefits. Additionally, you begin to become a bit of a local figure when you begin to perform in a town. When you are recognized by locals due to your performances, they will usually take a liking to you, that is of course considering you didn’t botch the performance they recognize you from.

Coming up with a unique routine for your entertainer to perform can be a lot of fun, and can be used to an advantage in combination with this background feature. As a traditional entertainer, it could be a little bit harder to work your way into places where an everyday musical performance just won’t be enough. For instance, a gladiator could use their fighting skills to work their way into an arena or an underground pit fighting ring, an entertaining magician could use their talents to gain access to a prestigious mages guild, and a ranger could gain a place among bandits with their feats of archery. Remember, not everything is as easy as plucking a lute, villains need entertainment too.

Customizing Your Entertainer

When you decide to use the entertainer background, you are granted proficiency in the Acrobatics and Performance skills as well as proficiency with a Disguise Kit and one musical instrument of your choice. These are great proficiencies for any typical entertainer, but that may not be what you’re going for so don’t be afraid to get creative with your DM and swap some things out. Different entertainers use different skills which is why a pit fighter may want to swap out the Acrobatics proficiency for Athletics and a magician may want to use Arcana. A rogue may want to use Sleight of Hand to pickpocket the audience while they are distracted by the show, or maybe even use Stealth to hide in obvious locations until they receive their cue to join in. A Disguise Kit is useful for any entertainer to make new costumes to perform in, but as I said before, not every entertainer is going to be musically inclined so you might want to switch out the instrument proficiency for something else. That’s fine, just make sure you work with your DM to come up with something appropriate.

On top of the skills and tool proficiencies, you also get a small list of starting equipment. This list includes a musical instrument of your choice, the favor of an admirer like a love letter, a lock of hair, or a trinket, a costume, and a pouch of gold coins. Just like the proficiencies you are granted, you can swap out these pieces of starting equipment to better suit the needs of your character. If you aren’t a music entertainer, feel free to change your one musical instrument to another tool or item that you and your DM decide you can use for your routine. You can also have fun coming up with the item that is your token from a loved one, or you can just forgo it if you don’t want to live up to the thirsty musician trope, which makes this a pretty good chance to reiterate, not all entertainers have to be bards.

Entertainer Variant: Gladiator

The PHB also offers a variant for this background which is the Gladiator background. However, as with the Spy variant that I mentioned in Exploring the Criminal Background, I don’t feel this was worth Wizards of the Coast making it a variant. They just tell you to swap out the proficiencies and tools you don’t want for other ones and make no effort to offer a variant feature, proficiencies, or starting equipment. They could have easily made gladiator an option on the list of routines available to choose from, leaving it up to you to swap things out as needed, and it would have been fine as it was. 

Suggested Routines by Class

Every class in Dungeons & Dragons utilizes different skills and abilities, and therefore, would go about entertaining others in different ways. This list will provide my suggestions for which of the provided routines in the PHB work well with each class, as well as at least one new routine fit for that class.


Instrumentalist, performance artist, prop comedian, storytelling


Fire-eater, gladiator, strongman


Actor, jester, instrumentalist, master of ceremonies, poet, singer


Evangelist, fortuneteller, poet, spirit medium


Animal wrangler, fire-eater, storyteller


Athlete, gladiator, jouster, tumbler


Acrobat, contortionist, dancer, juggler, tumbler


Actor, athlete, evangelist, jouster, poet, storyteller


Animal wrangler, juggler, trick shot performer, tumbler


Juggler, knife-thrower, sleight of hand trickster


Actor, magician, storyteller


Actor, fortuneteller, magician, spirit medium


Fortuneteller, magician, storyteller


  • Entertainers use a variety of skills and abilities to put on their performances and can be much more than just a regular bard.
  • Each entertainer has a routine they can perform that showcases the best of their abilities.
  • The background feature By Popular Demand can earn you free food and lodging for a job well done.
  • The Gladiator variant was a nice thought but could have just been added to the list of available routines since it doesn’t do anything different.
  • If you aren’t playing a bard, you can work with your DM to swap out the musical instrument, or any of the other proficiencies granted by this background, for any others that would fit the character you’re creating.
  • An entertaining performance doesn’t have to be just song and dance, they can use any number of different skills allowing you to use this background with any available class.

If you would like the full details of this background for use in your games, you can find it in the Player’s Handbook.

About The Author

Justin Dixon
Justin Dixonhttps://help-action.com/
Dix has been playing D&D for over 7 years and has been a professional dungeon master for about 3 years. He has been a featured author in multiple releases from Grim Press including Creatures of the Underdark and soon The Goblins of Beetle Hollow from Crumbling Keep. He has worked with the acclaimed pop-up tavern Orcs! Orcs! Orcs! He is the producer for the Help Action podcast and played Amelia Whiteheart on the live play podcast The Swordcast Adventures.

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