Exploring the Entertainer Background

The Entertainer background gives players an opportunity to bring their love to roleplaying and acting deeper into the game, and have their character do the same. Any character with the entertainer background gets a touch more bard-y, opening up their social options and for many of the classes answering the question of “what was my character doing before the campaign began?”

Key questions to answer for the entertainer background no matter what class you choose are:

• Who is the admirer whose favor you earned?
• How did you come across your musical skills?
• What is your routine?

The Gladiator variant is a great way to adapt the background to more martial classes.

*cue Enter the Gladiators*
Check out past background articles here: Acolyte, Charlatan, Criminal

Barbarian Entertainer 

Jock class clown. Done. Next.

Barbarian entertainers could have been keepers of the culture of their tribe, versed in their songs and stories. They could use these stories as touchstones of their own lives, modeling themselves after legendary ancestors or cultural heroes. 

Barbarians offer the chance to play a fish out of water just on the basis of your class. You originate outside of the bounds of civilization and so must live within a new culture. What happens to those who miss their culture? 

A barbarian entertainer spreads their culture through their raucous epic poems recited at the local tavern. This background allows you to help out the party by earning gold in town and possibly a place to sleep. Some models of barbarian entertainers could be heavy metal rockers, punk bands, or yodelers (please somebody play a yodeling dwarf barbarian).

If you choose the gladiator variant, consider how your character began to fight in the arenas. Was it a choice or were you forced to fight? Do you see yourself as a gladiator in this strange new world? Why leave the arena to seek glory in dungeons?

Bard Entertainer

Is a bard who does not entertain a good bard? Bards with the entertainer background supercharging their class-given skills to push them into the archetypical crooner of ballads and songs.

Your token from your admirer can serve as a basis for your turn to adventuring. Perhaps you need to prove yourself to your love? Perhaps you adventure for even more stories and epics to add to your repertoire. 

A bard as a gladiator is an interesting concept, not only using their skill as an artist but applying their martial skills in order to gain fame and glory. Bard entertainers should spend extra time focusing on how they acquired their skills and why they chose this way of life.

Cleric Entertainer

Sometimes the best way to draw the flock to the faithful is to give ‘em a show. Clerics with the entertainer background can take as an example the preachers from the Great Awakening period or other modern religious figures who command crows less through their religious wisdom and more through the force of their personalities.

You can also incorporate your music as part of your worship for your god. Bach and other composers who created beautiful works of art in honor of their faith could be examples here. A cleric could even see their art simply as a pure expression of the order and goodness of their god. 

Clerics who worship more martial gods would to well to choose the gladiator variant. This would be a direct expression of their faith – where else can you honor Kord but on the floor of an arena? What else proves your god is the greatest of all martial gods than winning in battle?

Druid Entertainer

Who doesn’t like a dancing bear?

Druids may find their place in the world by performing for others. You can choose to combine aspects of the bard and cleric in your background, perhaps finding your connection to the natural world through your art, or choosing to spread the Old Ways through song. 

Perhaps busking was the way you found to fit in with civilized society. If you choose the gladiator variant, consider how you use your connection to nature to add some panache and flair to your combat.

Druids aren’t known for their humor or their artistic streak, so this background can add some much-needed dimension to your character. Perhaps a satyr or nymph taught them how to play the panpipe or harp. If you have a familiar, how can you incorporate them into your act?

Fighter Entertainer

The gladiator variant is made for you.

Whether it is the valiant, honor-bound fighter, or the street brawler, a fighter gladiator is a great combination. Extra social skills are a great addition to your character, and you can always count on a hot meal. There is a great opportunity to play into a kind of hedge knight, not noble-born but presenting a kind of larger than life persona of a gallant. 

The fighter who chooses an artistic path could be a good addition to parties without a face character. They can help smooth over relations with disgruntled guards with either a well-placed word or blade. 

Fighters with the entertainer background may have picked up their fighting and musical skills at the same time, or maybe as part of an order of fighter-singers. This could form the basis of a larger connection to an organization in the world. Such ideas can help integrate your character more into the world and help build story connections that your Dungeon Master can then exploit — or, um, fashion into an enjoyable time.

Monk Entertainer

A monastery full of clowns. Just sit with that image for a bit.

But seriously, monks with the entertainer background can incorporate the archetype of the warrior-poet present in many martial cultures, from medieval Japan to Iron Age Celtic tribes. Monks can easily apply the discipline they learn as part of their class training to acquiring an artistic skill and then using that skill as a way to raise money for the monastery. 

A busking monk performing tricks with a begging bowl fits right into a Dungeons & Dragons world. Alternatively, you could have your character as part of a circus, their class skills a result of life in the circus. I would totally want to see a halfling circus full of monks shadow stepping and ki-punching all over the place. 

Monks, like Barbarians, are also fishes out of water. They grew up in a bubble in the monastery, so consider their expectations for the world, is it a place of wonders or a place of unknown fears.

Here are some monk entertainer traits to honk at:

Paladin Entertainer

Bring your natural charisma to the next level. Paladins can use their inherent force of personality to expand their influence and further their commitment to their oath by expressing their art in a public setting. 

An oath of the ancients paladin could see their music as an expression of their connection with the natural world and the fey. An elf paladin may find that the entertainer background fits perfectly with their character’s desire to express beauty in all things, in combat, and in song. A dwarf paladin could compose battle hymns to keep their fellow warriors steady in the face of a hoard of slavering orcs. 

The entertainer background offers paladins a way to engage with their religious culture on a deeper level, or even to buck the norms by composing bawdy sonnets about their god and all their supposed love affairs. Music, drama, and poetry have always been deeply entwined with cultic and ritualized practice in many human cultures so this intersection gives you an opportunity to do some deep-level world-building. 

Or, you know, be a holy casanova. 

Ranger Entertainer

The first real-world person that comes to mind is Anne Oakly, a sharpshooter and entertainer from the Wild West Show days at the end of the 19th century. She was famous for her skill and performed before heads of state and royalty. Why not have your skill with the bow be how you entertain, or your skill with wielding two blades.

Ranger entertainers that want to embrace more of a bounty hunter vibe could use their skill with the lute as a cover or as a way to gather information about potential bounties. You could use your social skills to help negotiate bounties to add some gold to your pocket or to get into restricted areas. 

Rangers are naturals at exploration, and like many common “lower class” jobs they may be able to sneak into parties relatively unnoticed, hiding in plain sight. Rangers also fit right at home in circuses, using their animal companions as part of their act. Druids don’t have the dancing bear market cornered after all.

Rogue Entertainer

Sometimes people will pay to have knives thrown at them. Rogues make natural entertainers, perhaps leaning more into a charlatan archetype. The rogue entertainer can put on a show as good as a bard, and perhaps come out ahead, stealing gold from people’s pockets as he steals their hearts.
Rogues can benefit from the cover offered entertainers – what better way to get into a noble estate than as a traveling balladeer with fresh songs and entertainment for the noble lord? The entertainer background also offers rogues a non-criminal angle. You could play more of a rake, and less of a crimelord with this background, being someone more interested in enjoying life than squeezing every last gold piece from it. 

Where bard entertainers might travel for fame and fortune, rogue entertainers may travel for the thrill of a new romantic conquest in each town, or simply to follow their more sensory desires.

Here are some traits to consider for your rogue:

Sorcerer Entertainer

If you’re not wearing a top hat, you’re not doing it right. 

Sorcerer entertainers have embraced their charisma and use it to bring joy, tears, and awe to the crowds. Sorcerers excel in playing into the stage magician stereotype. Your act could be using Prestitigitation to amuse crowds and to earn gold. Perhaps you turned to showmanship after your powers manifested.

Sorcerers with the entertainer background would fit easily into a circus-centric upbringing, perhaps learning to manage their powers with the help of other sorcerers. Think about your connections to the people you work within your act, whether that is your party or a group of non-player characters. 

If you decide to go with the gladiator variant, your powers likely give you a special edge over the other combatants. What brought you into the life of combat in the arena? Do you enjoy killing, or do you do it as a way to earn the life you deserve? Are fame and fortune the driving factors for you, or do you not trust yourself to live safely among normal people?

Here are some traits for your sorcerer:

Warlock Entertainer

I’d make a pact with an elder god to become a celebrity.

Your skill as an entertainer could come from the same pact that gave you your supernatural powers, or it could be the thing that drew the patron to you. Perhaps you were captured by an Archfey after they heard you singing in a glade and you negotiated a pact as a means to escape their realm.

Find a way to tie your motivation to form a pact with your background to create a compelling personal quest or motivation. Warlocks are unique in that what defines them more than any other is the kinds of choices they make to gain power. Instead of studying magic like a wizard, or investing the time to learn a martial skill like a fighter, warlocks agree to serve a patron in exchange for quick power. What made you choose that power if your life up to that point was working as an entertainer? 

Was it to impress your admirer or to gain your “fair share” of fame and fortune? The answer can unlock an entire characterization.

Here are some traits for your warlock:

Wizard Entertainer

A true renaissance man… or the wizard from The Wizard of Oz.

Wizards with the entertainer background could be for the player that wants some of the social skills of a bard but the spell list of a wizard. Wizards aren’t naturally charismatic, so your entertainment may not take the same form as a sorcerer or bard. Perhaps you are a professor capable of enthralling audiences with your detailed explanations of arcane sciences. 

Wizard entertainers could also be stage magicians, but something about an illusion wizard with the entertainer background points to somebody who not only impresses with tricks but creates immersive and magical illusions to entertain the rich and powerful. 

The biggest question to ask yourself is why and how your wizard acquired their performance skill. Were they working as a minstrel as a way to pay for their magical education? Or, did they pick up music as a way to soothe their minds after a long day of magical research?

Here are some traits for your wizard:

Check out past background articles here: Acolyte, Charlatan, Criminal

Image by Jan Matejko – http://cyfrowe.mnw.art.pl/dmuseion/docmetadata?id=4795, Public Domain, https://commons.wikimedia.org/w/index.php?curid=43350542