Overview
A thought occurred to me today. I was thinking about a PC I'd made a while ago that I think I may use as an NPC in one of my other campaigns (considering that I'm very rarely a player these days when it comes to D&D 5e.) I want to make a jester... but specifically I want to make a jester that's something just a little bit more than a jester.
This is a "master of deception and disguise" character archetype. This is the type of character that NPCs look at and think "I can trust them" right before getting stabbed in the back. This is a social PC, for sure, but one that can also have excellent combat potential depending on certain choices.
Race, Class, Stats, and Background
Depending on what you - the player - wants and what your DM will allow, there are a few options. There are going to be some multiclassing options here, for flavor. There's also going to be Unearthed Arcana (playtest material) and a few things from Matt Mercer's Explorer's Guide to Wildemount.
Let's talk class first. I want to start with Bard - specifically the College of Satire subclass. (Unearthed Arcana 2016) This specific subclass has a serious "court jester" aesthetic. It's a class that promotes luck and mobility; you are, after all, a tumbling fool. If your DM allows Unearthed Arcana and you don't like multiclassing, then take all 20 levels in this class. Charisma is going to be your highest stat, probably followed by Dexterity. If Unearthed Arcana isn't your DM's cup of tea, (or your own) but you want to a play a Bard, College of Glamour (Xanathar's Guide) is my next choice. That class centers around distraction, enchanting enemies, and illusions - perfect for a jester hoping to keep others occupied while their party members are sneaking about, causing trouble.
If you're looking to multiclass, the way I see it, if you've got the jester aesthetic from Bard, there are three major directions to take your secondary skillset:
- The Spy. Although you appear to be a jester, you're actually a master spy or assassin.
- The Warrior. Although you appear to be a jester, you're actually some kind of knight or special bodyguard for those that you serve.
- The Mage. Although you appear to be a jester, you actually have significant magical powers outside of your bardic abilities.
For the spy archetype, I'd pick the Assassin Rogue (Player's Handbook) as my second class. You get the disguise and poisoner's kit proficiencies for extra espionage opportunities. Level 9's Infiltration Expertise and Level 13's Impostor features will really help along the "master of deception" angle. In fact, if you go this route, I'd say take more levels in Rogue than Bard. 14 levels to 6, to be exact so you can get Evasion at Rogue 7 and Blindsense at Rogue 14. Dexterity is probably going to be your priority stat, followed by Charisma.
The warrior archetype could go with Fighter if they wanted, but personally, I like Paladin for the Charisma spellcasting to go with our Bard. Depending on who you previously "jested" for, there are a lot of options for oaths. If you're still loyal to who you worked for: Oath of the Crown. (Sword Coast's Adventurer's Guide) If not, you could pick Oathbreaker, (Player's Handbook) Oath of Vengeance, (Player's Handbook) or Oath of Treachery. (Unearthed Arcana 2016) That's up to personal preference. Either way, Charisma is still going to be high, but I'd prioritize Strength over Dexterity unless you're planning on using a finesse weapon and not planning on using heavy armor. There are some interesting and kind of unconventional Paladin aesthetics to be explored with this version of the build. I like this option because how many levels you decide to take in either class doesn't really matter.
Lastly you have the mage. Sorcerer could work, definitely. Subclass in that case doesn't really matter with them for this build, and they have the benefit of using the same spellcasting attribute as Bards. Wizard would be my personal first choice, and you could go with either School of Enchantment or Illusion. (both Player's Handbook) If you're going with Illusion, I'd say that Wizard 10 / Bard 10 is the best split so you can get the Illusory Self feature. You don't need much from Wizard after that. Enchantment Wizards might want to take a similar path to Rogues and do Wizard 14 / Bard 6 so you can get the Alter Memories feature. What's better than making people believe that you're not doing anything wrong? What about making them forget you were even there at all? Intelligence and Charisma are going to be your main stats.
Explorer's Guide to Wildemount has a great background to encompass the idea of a minstrel who's not just a jokester or entertainer. The background is called "Grinner." It's a network of bards that are actively working against tyranny and have secret songs to convey certain messages. A DM can flavor this background to fit their world or campaign setting in a really fun way, I think. There are a lot of directions it could take. Entertainer or Charlatan (both from Player's Handbook) would also be an effective choice while keeping the jester aesthetic. Grinner works well for the spy archetype. I think that the other two might be more effective for the warrior or mage.
Each of the archetypes also has a different "go-to" background in my mind if you'd prefer those:
- For the spy, pick the Spy (Player's Handbook, Criminal Variant) if you don't like any of the other options.
- For the warrior, you can go with either Knight (Player's Handbook, Noble Variant) or Knight of the Order (Sword Coast Adventurer's Guide) if you don't like Entertainer or Charlatan.
- For the mage, my choice would be Sage (Player's Handbook) if you don't like Entertainer or Charlatan.
Race doesn't matter for this build. This is a Charisma-focused character, so any race that gives you a buff to your Charisma will be useful to you. Off the top of my head, a few suggestions of mine would be half-elf (Player's Handbook), changeling (Eberron), or tiefling (Player's Handbook) - including most of the tiefling subraces that come with Mordenkainen's Tome of Foes (if you're using those.)
Roleplay Potential
A character like this is fascinating for a number of reasons. Personally, I like the idea of characters presenting themselves as one thing - a jester, in this case - and actually being something else or having an unexpected skillset as well.
From a backstory perspective, it's so fun to explore. Why did they fall into this job? If they left it behind, why? How this skillset is revealed can also be a very wild ride and a ton of fun. I love the moment of a party being like "if only any of us knew how to make poison" and this character being like "um, actually... I can make poison."
This character is essentially "playing the fool" to get into places that might be harder to get into. A noble court, for example, might accept a jester into their fold, not believing it to be consequential. Jesters would also fit into a tavern setting, a theater, or a circus. Most people would assume that they belong. With good Charisma, they might be able to convince the actors or performers that they're part of the cast that they just haven't met. Who pays any mind to a jester who's not performing? Meanwhile, the character is listening in on all the gossip and getting a sense of the political landscape. They could also be poisoning drinks, subtly casting a spell, or positioning themselves perfectly for an ambush. On the other hand, when a jester is performing, who can look away? While they're doing that, what's the rest of the party up to? Probably stealing something, trying to find a certain person or piece of information, or some other shenanigan.
Overall, this is a character of surprises, and who doesn't love a good surprise in Dungeons and Dragons?
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