Entertainer Background Guide 5e: Putting On A Show

Whether you’re a bard singing for their supper, an assassin who honed their infiltration skills on the stage, or an illusionist wizard who specializes in dazzling displays of arcane pyrotechnics, the Entertainer background is a great basis for any character in D&D 5e who turns their flare for the dramatic into a (somewhat) steady source of income. 

The Entertainer 

Skill Proficiencies: Acrobatics, Performance

Tool Proficiencies: Disguise kit, one type of musical instrument

Languages: None 

Equipment: A musical instrument (one of your choice), the favor of an admirer (love letter, lock of hair, or trinket), a costume, and a pouch containing 15 gp

Feature: By Popular Demand

Your skills as a performer mean that you can almost always find a stage and an audience in every new town or city you travel to. Usually, this means a tavern, but you might also find work at a local circus, or in the court of a local noble, depending on your skillset. 

In the tradition of traveling artists, thespians, and musicians everywhere, you receive modest lodgings and food as long as you perform every night. While your residency at a local establishment continues, you become something of a minor celebrity in the area, which may make the locals well-disposed towards you. 

You feel most at home in front of an audience of cheering fans, beneath the lights of a stage. Whether you’re a poet who stirs the emotions of the crowd, a musician who plays to enraptured fans, a tumbler, juggler, or comic, your art is your life’s passion. 

While the Entertainer background lends itself most obviously to bards, there’s no reason a fighter couldn’t find work as a strongman in a circus, lifting weights and bending iron bars for the amusement of the crowds.

A wizard or sorcerer with a knack for illusion or evocation magic could hold their audiences spellbound with displays of colorful smoke, gouts of flame or a play performed entirely by illusory actors. An artificer might even turn their hand to stage magic, or put on an exciting firework display. 

Entertainer Routines

Every Entertainer worth the price of admission has a routine. The best entertainers have more than one, and can spice up each performance to keep the crowd coming back for more. 

When you choose this background, pick between one and three routines, or roll a ten-sided die on the table below. 

d10Entertainer Routines
1Actor
2Dancer
3Fire-eater
4Jester
5Juggler
6Instrumentalist
7Poet
8Singer
9Storyteller
10Tumbler

When you roleplay your performance, while a juggler, tumbler, or other physical art might just require a Dexterity (acrobatics) or Dexterity (sleight of hand) check, if you’re an actor, a poet, or a storyteller, it can be fun to memorize a few lines of verse or a good joke.

As a dungeon master, I’d happily give inspiration to any player who really goes the extra mile to make their performance captivating. 

And by a sleep to say we end the heartache and the thousand natural Shocking Grasps…
Source: Hamlet (1948)

Suggested Characteristics

Entertainers require the strength of charisma to command a room and hold an audience’s attention. As such, they tend towards having forceful, flamboyant personalities. 

When you choose the Entertainer background, choose a Personality Trait, Ideal, Bond, and Flaw from the tables below, or roll dice to randomize the process. Alternatively, you can make up your own. 

d8Personality Trait
1I know a story relevant to almost every situation.
2Whenever I come to a new place, I collect local rumors and spread gossip.
3I’m a hopeless romantic, always searching for that “special someone.”
4Nobody stays angry at me or around me for long, since I can defuse any amount of tension.
5I love a good insult, even one directed at me.
6I get bitter if I’m not the center of attention.
7I’ll settle for nothing less than perfection.
8I change my mood or my mind as quickly as I change key in a song.
d6Ideal
1Beauty. When I perform, I make the world better than it was. (Good)
2Tradition. The stories, legends, and songs of the past must never be forgotten, for they teach us who we are. (Lawful)
3Creativity. The world is in need of new ideas and bold action. (Chaotic)
4Greed. I’m only in it for the money and fame. (Evil)
5People. I like seeing the smiles on people’s faces when I perform. That’s all that matters. (Neutral)
6Honesty. Art should reflect the soul; it should come from within and reveal who we really are. (Any)
d6Bond
1My instrument is my most treasured possession, and it reminds me of someone I love.
2Someone stole my precious instrument, and someday I’ll get it back.
3I want to be famous, whatever it takes.
4I idolize a hero of the old tales and measure my deeds against that person’s.
5I will do anything to prove myself superior to my hated rival.
6I would do anything for the other members of my old troupe.
d6Flaw
1I’ll do anything to win fame and renown.
2I’m a sucker for a pretty face.
3A scandal prevents me from ever going home again. That kind of trouble seems to follow me around.
4I once satirized a noble who still wants my head. It was a mistake that I will likely repeat.
5I have trouble keeping my true feelings hidden. My sharp tongue lands me in trouble.
6Despite my best efforts, I am unreliable to my friends.

Variant: The Gladiator 

Few bards will ever know the uproarious cheers of a whole coliseum erupting at the sight of blood. Trained in the arts of showmanship and combat, the gladiator is as much an entertainer as any troubadour or minstrel. 

If you choose this variant of the Entertainer background, you have mastered the art of stunt fighting that rests a razor’s edge away from outright violence. You’re somewhere between a warrior, a professional wrestler, and a medieval reenactor.  

When you use your By Popular Demand feature, you find a place to perform anywhere where combat is held for entertainment — perhaps a gladiatorial arena or an underground fight club for the amusement of local nobles. 

You can replace the musical instrument in your equipment loadout with an inexpensive but unusual weapon, such as a trident or net, that likely forms the focal point of your persona. Personally, I’d also come up with a cool name, before the DM has an NPC come up with one for you.