Roguish Archetype: The Jester [Fifth Draft]

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The last time I touched this one is three years ago? My god, how time flies.

I've got a backlog of revisions due a mile long, and I'm not content to just edit old content. I've learned so much in the time I've spent doing this, and I aim to re-imagine old options, making them distinct, well-rounded, and complete!

The jester, for one, had a unique casting system that I always felt was somewhat lacking. It was very much "Here are some spells! Make the spells happen!" without any distinguishing system mechanics behind them.

No longer! The jester thematically was always about blind luck, silly situations, and grim humor over sheer utility, so I've re-imagined it as an extremely variant 1/3-caster that relies mostly on luck to determine its spell list.

I expect that this won't be a final version (woe betide me, a sixth draft?!), but it's a bold reworking that I imagine will carve more of a niche for itself than the four other jesters that have come before it.

CHANGELOG:

• Arcane Buffoonery is now Arcane Wit, which comes with a full (if decidedly different) 1/3 caster spell progression!
• Harlequin's Mask doesn't specifically reference vicious mockery, because it created weirdness whether it or Arcane Wit should be first.
• New Ability: Tumbling Fool! Get some extra mileage out of your Disengage, roll around the battlefield like a maniac.
• Cruel Comedy has been raised from 9th to 13th level, which seems like a better space given what it does.
• Most of the spells you know are completely random! But don't worry, they reset every long rest.
• Now uses a 1/3-caster version of warlock spell mechanics, instead of eluding to it sidelong like it did before.

CONCERNS:

• Oh, so very many.
• Will randomized spellcasting be fun?
• Is 1/3-caster warlock progression balanced?
• Is Arcane Wit clear in its language as to what it does?

WHAT I LEARNED:

• I guess if I need to revise my entire catalog, I might as well start right now.

Roguish Archetype: The Jester [Fourth Draft]

A fourth draft? Well, the confusing morass that was applying sneak attack damage to spells sure needed one, and so a fourth draft is what we've got!

I tightened up what needed tightening up, I fixed what was inelegant, and what we have now is a beautiful, fun archetype that synergizes very, very well with existing rogue mechanics.

And how does it do that, you ask? To the changelog!

What I Changed:

• Harlequin's Mask no longer gives charm immunity. Rather, it gives you the ability to cast vicious mockery as a bonus action (thus intentionally competing with Cunning Action much as the Mastermind rogue does with the Help action). When cast in this way, vicious mockery deals no damage, thus keeping DPR similar.

• Arcane Buffoonery and Jesting Magician now only grant three spells each, keeping your total arsenal of spells down to three (and then six) specific spells per short rest, that can each be cast once. 

• Cruel Comedy has been completely reworked. It now additionally buffs vicious mockery, giving you advantage on your next attack after using it, thus allowing you to use vicious mockery to get sneak attack damage without directly applying the damage to the cantrip. The charm immunity of Harlequin's Mask now finds itself here, as charm immunity is much better as a 9th level feature in any case. 

Concerns:

• I better damn well have this right after four drafts. 

What I Learned:

• Keep It Simple, Stupid. I was trying to make the features more elaborate to shoehorn together two things that don't work. Rather, use what already exists more fully to make the new stuff function.

Roguish Archetype: The Jester [Third Draft]

With a third draft, I think the jester is finally either complete or very well nearing completion. Mechanically sound, balanced, and with abundant flavor, this definitely looks like a rogue archetype worth playing.

A lot changed in this draft, and not all of it obvious, so let's have a look at the changelog to see what's what:

What I Changed:

• I used an entirely new template for this! Based off of the formatting I used on the Vampire PrC, the type is smaller and the headers are a closer match to what the PHB uses. Overall, it's cleaner and gives more room to add graphics and features while maintaining readability, which is always a good thing.

• Fixed my Photoshop (finally) to allow for high-resolution PDFs. A great thing, which will mean I'll probably have to go back and high-resolution all of my previous work (a less great thing). 

• I added faerie fire and feather fall to Arcane Buffoonery, and enthrall, mirror image, and misty step to Jesting Magician. I capped Arcane Buffoonery at "choose four spells," and Jesting Magician at "choose five" - one less than Jesting initially got, but the fact that you can choose from a list means it needed the minor rebalance. 

• Cruel Comedy can now be used defensively as soon as you are the target of an attack. This means a gamble for the jester: Do you wager that the enemy is going to fail its Wisdom save, and then miss on its attack against you while it is suffering disadvantage, or do you expect that the enemy will make its save or hit regardless, and take the damage while using Uncanny Dodge to mitigate it? 

• Cruel Comedy also has had the verbage changed up on the qualifiers for vicious mockery's sneak attack, which should make it come up more often. 

Concerns:

• Cruel Comedy doesn't have the clearest, most intuitive verbage for the aforementioned sneak attack, but I truly believe it's about the best I could do. Making sneak attack apply to spells with saves is hard work. 

Roguish Archetype: The Jester [Second Draft]

So, other than one major hiccup, the rough draft was mostly okay!

Well, as mostly-okay as rough drafts ever are. It had a bunch of bumps that needed ironing out, but iron them out I did, and we have a rather promising second draft before us.

So let's take a look at the changelog, then, to see why this is so much better.

What I Changed:

• Midway through the rough draft, I changed Pratfall to Cruel Comedy. Pratfall almost perfectly emulated another core rogue feature, which didn't seem like anything close to good design, and so I changed it.

• Cruel Comedy is designed to compete with Uncanny Dodge somewhat - when hit by an attack, you can decide whether to ignore half the damage or to cause minimal damage and disadvantage on the enemy's next attack. When taking damage from a spell, however, it's more of a no-brainer, and you can insult the asshole who hit you to your heart's content. 

• I streamlined Cruel Comedy from the rough draft - instead of emulating vicious mockery, it now just casts vicious mockery. This is a trade-off, as it decreases the damage done from 1d10 to 1d4, but it also has a massive buff because...

• Cruel Comedy now allows you to apply Sneak Attack damage to vicious mockery once per short rest. This can function off a standard casting, or the revenge-casting that Cruel Comedy provides. 

• Jesting Magician now buffs the spell slot level of spells cast from Arcane Buffoonery to 2nd level - which is nice for color spray, and not much else. 

• Included a sidebar on the last page directly addressing the multiclassing spell slot weirdness. 

Concerns:

• Spell progression here is still weird, which makes sense because I've been doing weird things with the archetype. I don't think it's terribly unbalanced, though - you may get extra spells, but only four with any direct combat application, and your spell level caps at 2nd level rather than 4th. 

• Other than that, not much. I think this archetype is good to ship!

What I've Learned:

• Roguish Archetypes are weird. Unlike paladin oaths and warlock otherworldly patrons and pacts, rogues have most of their combat potential stored in core features of the class that cannot be directly altered, really. Thus, roguish archetypes are great for flavoring the core experience of being a rogue, which is essentially what they do in canon materials. 

• It's really, really fucking hard to find pictures of high fantasy festivals. Seriously, try it. It's even more bananas than finding a non-sexy female necromancer. 

Roguish Archetype: The Jester [ROUGH DRAFT]

It's not a warlock! It's not even a paladin!

It's a rogue! Or, really, it's a Jester.

The Jester was a fan-favorite of 3.5, a comical magical rogue who utilized tricks, arcane know-how, and grease paint to entertain, beguile, and frequently annoy both friends and foes alike.

There was some hullabaloo from people involved with 5e about the Jester early on in its production run, and seeing it as a genuine subclass in the core rules seemed like a possibility. Sadly, though, this was not in the cards, which brings us to this offering, here and now.

Features:

• Charisma-based spellcasting similar to the inherent magic some races get. No spell slots here, just spells that you can cast once per short rest. 

• Being clumsy to escape damage: it's not a bug, it's a feature.

• Burns so sick they hurt your enemies' brains. 

• Face-paint and high-level death avoidance.

Concerns:

• Roguish Archetype design schema is kinda weird. Most archetypes (including the new Mastermind) follow a two-combat / three-utility delineation of class features, regardless of the level those features are awarded at. However, Swashbuckler and Arcane Trickster break this hard, themselves having only one utility and four combat powers. In the end, I shrugged my shoulders, said "meh," and attempted to have almost every feature in this archetype have both a utility and a combat purpose. 

• Multiclassing with this is inherently weird. Unlike the 1/3 caster options like Arcane Trickster, this has no spell slots, and the spells are cast entirely as a function of class features. Therefore I'd consider this not even a fraction of a caster option when determining multiclass spell slots - it's zero caster. 

• Arcane Buffoonery and Jesting Magician give more spells than you'd normally have at your equivalent level of Arcane Trickster - however, you have no choice in which spells you receive, and ultimately get less spells overall. 

• I considered allowing vicious mockery to synergize with sneak attack, because that'd make some amount of thematic sense, but decided against it on the grounds that it might break the game in unexpected ways. So: would it?