At the request of a reader, this article in the History of the Monk offers an overview of the monk-friendly prestige classes of 3.x D&D. In the interest of keeping this manageable, I’m really only addressing 3.5; just about everything from 3.0 was updated at some point, and I don’t think the rules tweaks that got them there are going to be interesting enough for my time or yours. These are in no particular order, except maybe some semblance of publication order.

Part One | Part Two | Part Three | Part Four | Part Five | Part Six | Part Seven


The Shadowdancer

The Shadowdancer was, to me, one of those classes that is cinematic and exciting, but it’s not at all obvious which core classes feed into it. It doesn’t grant any of the critical damage-increasing mechanics for rogues or monks, it’s a sharp tonal shift for anyone who got this far as a ranger, and while its skills scream “bard,” its features don’t boost a bard’s melee capabilities nearly enough to sell it or make up for the absence of spell progression.

  • The skill requirements are steep, and many classes are looking down the barrel of cross-class skill ranks for something. Of the Player’s Handbook classes, bards, monks, and rogues can all get there without going cross-class. The earliest that anyone can enter this class is 8th level, since you need a pre-existing 10 ranks in Hide, and given the feat requirements, you need to either be a human or pick up one or more of those feats from a class’s bonus/virtual feats. The monk, for instance, can choose Combat Reflexes as a bonus feat at 2nd level, and this class is one reason you might choose Combat Reflexes over Deflect Arrows.
    • If you’re thinking to yourself, holy cow that is a lot of pre-planning that I need to put into my build (or else have a DM who is way more relaxed about respending build choices than the books recommend), then you’re right. That is one of the great truths of prestige classes: they are the bane of organic character building.
  • 6 + Int skill points per level and a broad, roguish skill list.
  • d8 Hit Dice. Better than the rogue or bard, on par with the monk.
  • Weapon and armor proficiency are rogue-oriented, and if you’re a monk, this is just wasted page space.
  • Hide in Plain Sight is the foundational Shadowdancer feature: even while you’re being watched and have no cover or concealment of your own, you can blend into a shadow up to 10 feet away. (But not the character’s own shadow.)
  • Evasion is here for characters that didn’t take the monk or rogue paths.
  • Darkvision is here for some obvious reasons, but should probably have come one level earlier. (As a reminder, darkvision was comparatively rarer in 3.x, and its lesser cousin Low-Light Vision was more common.)
  • Uncanny Dodge is likewise here for people who didn’t come through rogue… or barbarian, but I’m going to say that’s a pretty small set. Fortunately for rogues, this gets kicked up to Improved Uncanny Dodge if you already have the lesser version, and Improved Uncanny Dodge has a level-scaling benefit.
  • Shadow Illusion grants silent image once per day. Um, woo? As with most illusions, it depends on your ability to be creative and your DM’s adjudication style.
  • Summon Shadow creates a flanking buddy. One without a ton of hit points, but I guess any damage spent on the shadow is damage not spent on the Shadowdancer. The XP hit (200 XP per Shadowdancer level, save for half) when your shadow dies – and loss of this feature for 30 days – is wildly unnecessary.
  • Shadow Jump is probably the feature that you thought you were getting when you read the class name – a bunch of in-combat teleports from shadow to shadow. Dimension door’s restriction that you cannot take any action on your turn after completing its transit is disappointing here, but since 3.x is overall way lighter on combat teleportation than 4e or 5e, this is still a pretty great feature.
    • From the monk’s perspective, this signature feature competes with Abundant Step, arriving one level earlier, having a lot more flexibility in daily usage, having much more demanding usage prerequisities (shadows, that is), and a much shorter maximum range. It’s kind of a wash.
  • Defensive Roll is a lift of a high-level rogue’s special ability. It’s not one of the very most in-demand of the special abilities, but it’s fine.
  • Improved Uncanny Dodge… because of all the same reasons I listed for its precursor.
  • Slippery Mind is another rogue special ability, particularly welcome for monks since taking this prestige class means ditching all of the core monk’s other high-level defensive features.
  • Improved Evasion does its thing, as the prestige class’s top-end feature.

So yeah, this prestige class is all about mobility and defenses, with a huge cost in offensive ability for literally any base class. Personally, I think Shadow Jump should be offered as a rogue special and an optional monk feature, maybe as the more ninja-like alternative to Abundant Step. In short, I am not sure the Shadowdancer is a good choice for any class, and certainly not the monk or rogue. It’s the only decent fit for monks in the whole of the 3.5 DMG, though. (Okay, I guess you could do a monk/assassin somehow to build a ninja’s ninja, but I’ve already covered the 3.5 assassin in way more depth elsewhere.)


Drunken Master

This prestige class comes from Complete Warrior, and it’s about as good-faith an effort to present “the Jackie Chan one” as I could ask for. If you’ve been reading my work here on Tribality for at least the last several months, you may recall that I had some not-entirely­-complimentary things to say about the presentation of Drunken Masters in D&D. Well, this… is a lot less bad than I had remembered. It’s Jackie Chan action comedy, all right.

  • d8 HD.
  • Very reasonable skill requirements. You could enter as early as 6th Three feat requirements, one of which is intrinsic to literally all monks ever (Improved Unarmed Strike).
  • 4 + Int skill points per level, in what is mostly the standard monk list, plus Bluff.
  • The Drunken Master has special dispensation to ignore the monk multiclassing restrictions. You can intersperse monk and Drunken Master advancement freely.
  • Drink Like a Demon is the core Drunken Master feature, consuming alcohol to turn Int and Wis into Str or Con, 2 points at a time. Deep-sixing your Wis is, er, something of a sucker bet for monks. Also a nightmare of on-the-fly stat recalculation, which only gets worse as you go.
  • Improvised Weapons is the beginning of the much more Jackie Chan-like thread in the class. This first feature just negates attack roll penalties and adds a 1d4 damage kicker to improvised weapons. This essentially replaces the damage scaling you’re missing out on by leaving the monk class.
  • Stagger lets you charge in not-a-straight-line and incorporate a Tumble check to avoid opportunity attacks as part of that charge.
  • Swaying Waist gives you a secondary Dodge target, against whom you receive a +2 AC.
    • For those who don’t speak 3.x, the Dodge feat lets you declare that you’re especially avoiding a specified enemy, and you gain a +1 AC against that enemy until the start of your next turn. It was tedious and piddly shit in actual use.
  • AC Bonus means you’re not completely cut out of the defensive scaling of being a monk.
  • Improved Improvised Weapons increases your damage kicker and lets you get a benefit from the type of improvised weapon you’re using, such as ladder granting reach. This is also the point at which the class turns decisively in the direction of weapon stunts and controlling enemies, in a way the core monk class does very differently.
  • Greater Improvised Weapons further boosts you damage kicker with improvised weapons.
  • Improved Feint and Improved Grapple come along as bonus feats in consecutive levels. Pretty sure they’re still inspired directly by the same Jackie Chan clip (or, you know, his whole oeuvre).
  • For Medicinal Purposes lets you convert incoming alcohol or alcohol already in your system to potions of cure moderate wounds, up to 3/day. Saves a lot of money compared to buying potions, but a long time to wait for (effectively) three 2nd-level spell effects. It’s a big step up from Wholeness of Body, which of course you don’t have if you jumped on the Drunken Master train (don’t drink and conduct trains, y’all; this metaphor has some problems) as early as possible.
  • Corkscrew Rush is a variant charge that trades the risk of falling prone at the end for the possibility of a bull rush and stunning the target. Giving monks super-good charge attacks – you know, like flying kicks or headbutts or whatever – is just a good start, considering how much effectiveness they lose by moving more than 5 ft. in a round.
  • Superior Improvised Weapons, mirabile dictu, increases your damage kicker with improvised weapons.
  • Breath of Flame converts alcohol in the Drunken Master’s body into a 3d12 fire breath weapon. As a free action. Drinking is a move action, though, so you really need to get tanked before the fight – any move actions you’re spending drinking are not full-round actions spent making all of your iterative attacks.

Overall, this class is kind of doing two barely-related things: alcohol magic and action comedy. I’m way more interested in the latter than the former, because ha ha, yer dude is drunk 26 hours a day is not a joke or character note that stays interesting for ten levels of play to me. All told, though, I don’t hate this, I’m just leery of its premise in the hands of some players. For the most part, you’re probably better off in terms of overall power if you stick with monk, but I’d have to do a lot of math to feel confident of that, and… I’m not gonna. I also just want to emphasize what a mess round-by-round ability score tradeoffs are.


Tattooed Monk

The Tattooed Monk is, for the most part, a monk who wasn’t getting enough weird abilities from their class, and decided that the solution was to chase an a la carte collection of supernatural and spell-like abilities, all stored in tattoos. The flavor text talks about this order being more rural or wild than others, and divided between worldly and ascetic monks, while the mechanics present something more about beast, plant, and landscape tattoos as a source of power. The much less disciplined, monastic tone is a lot cooler to me – I mean, I’ve watched Moana, and this is a perfectly good presentation for Maui sans fishhook. (The Tattooed Monk does not require ranks in Swim.)

  • d8 Hit Die.
  • Easily attainable prereqs, though the 8 ranks in Religion is probably a waste in the eyes of most monks. It certainly doesn’t factor into the class in any visible way. Two of the three feats are bonus feats for monks. 6th level is the earliest you can take this prestige class.
  • 4 + Int skill points, from a pretty typical monk skill list.
  • Some of your monk abilities – specifically unarmed damage, AC bonus, and speed bonus – all progress as if this were still the monk class.
  • At every odd-numbered level, you gain a new tattoo, so that’s five over the course of this 10-level class. You don’t gain any new feature at 10th level, which I think we would now call a blatant design flaw. There are a total of 30 tattoos offered in the writeup, and I’m not going to cover them all here – just a few highlights. Oh, and when tattoos need a scaling value (such as uses per day), it’s often equal to the number of tattoos you currently possess from this class.
    • Arrowroot and Nightingale both grant healing, but Arrowroot grants more healing that is others-only, while Nightingale grants a version of Wholeness of Body that only scales by Tattooed Monk levels, and can be used on oneself or others.
    • There are a whole series of ability-score boosting tattoos – Bamboo, Bat, Bellflower, and Butterfly. The gaps here are sort of odd, but Bellflower can boost any ability score… by a value equal to your Cha modifier. Because that’s something monks are likely to have a good score in.
    • A whole lot of these amount to a grab-bag of possible features and tricks up your sleeve, the kinds of things that might very reasonably show up if monks got “monk special abilities” at 10th level and above the way rogues get “rogue special abilities.” There are a lot of oddities in how these abilities scale by Tattooed Monk level, and thus stop scaling when you reach 15th level… just when the 3.x metagame is really blowing up.
  • As with the Drunken Master, you receive special dispensation to keep picking up monk levels. The only thing that makes this weird is that you can wind up with overlapping abilities such that neither of them scale up sufficiently, like their respective Spell Resistance features.

The Tattooed Monk is a great showcase of what the monk could be, but it’s stored in the awkwardness of a prestige class, and there are a lot of filler options that are minor-to-modest bonuses to this or that – enough to write down on your character sheet, probably not enough to feel like you’re actually great at that thing. I dunno, I’ve become quite enchanted with 5e’s far less mathy style. I can’t fully engage with 3.x on its own terms anymore.


Sacred Fist

This class requires you to have some amount of spellcasting, but really wants you to have a bunch of monk levels also. Its concept is “I rely on nothing but divine spells and unarmed attacks,” but it doesn’t allow you to keep picking up monk levels – and even more than that, you get locked out of this class if you take anything other than Sacred Fist levels, once you gain your first level in this prestige class. In short, 3.5 got way too wrapped up in No You May Not as a substitute for actual theme. That fault doesn’t belong to any one designer, of course. (Unless you have insider knowledge and want to spill.)

  • d8 Hit Dice, as befits both clerics and monks.
  • Interestingly, +1/1 BAB, better than either clerics or monks.
  • 4+ Int skill points, from a slightly stripped-down monk-like skill list.
  • Qualifications are fairly attainable; the most annoying requirement is probably the +4 BAB, since you kind of want to lowball either monk or cleric and spend the rest of your prerequisite levels on the other one. In all, I think you’ll wind up needing cleric 2/monk 4 or monk 2/cleric 4, or you’ll need to splash paladin rather than monk. (Don’t do that, it totally sacks the throughput of all those “+1 level of existing divine spellcasting class” bumps you get.)
  • The Sacred Fist keeps gaining unarmed damage as a monk, gains +3 AC and +30 ft speed over 10 levels roughly like a monk, and gains 8 divine spellcaster levels presumably like a cleric.
  • Sacred Flames lets you set your fists on fire (in that magical, not-hurting-you way) once per day (twice at 8th level). This adds your Sacred Fist class level and your Wisdom modifier to your unarmed strike damage, so reasonably we’re looking at +8 or so when you first gain this feature, eventually climbing toward +16 or so at Sacred Fist 10. The standard action that it takes to activate looks a lot more reasonable once you consider that we’re talking about 3-5 attacks in a round.
  • Blindsense lets you sense vibrations and whatnot out to 10 feet. Not super sure why this is here and not, say, in the monk class, but whatever.
  • Inner Armor is a serious but short term self-only defensive buff. +4 to AC, +4 to all saves, and Spell Resistance 25 is not a joke, assuming you’ve otherwise done your due diligence in getting good bracers of armor.
  • The Code of Conduct obligates the Sacred Fist to never use any kind of weapon save unarmed attacks, and to follow the prestige class’s strict multiclassing rules. Once you finish the class, I guess you’re either going back to cleric or looking for another prestige class, since you can’t go back to monk.

The Sacred Fist is one of the many prestige classes in 3.5 that sets out to resolve the problems in a particular multiclassing pair – Eldritch Knight, Mystic Theurge, and Arcane Trickster are some of the better-known examples of the same goal. It has far fewer Special Features and a lot more “progress as both Class A and Class B” going on, which you’re presumably fine with if you signed on in the first place. The spellcasting and melee combat abilities don’t need any more help to synergize – we’re talking about 3.5 here, so a cleric willing to self-buff is an unstoppable engine of destruction already. What’s that you say, you also spent a round getting Sacred Flames up and running? Well, yeah, that’s pretty boss.

Thematically, trying to fold the monk back into the ranks of ordained clergy by making them flashy asskicking clerics is a little weird to me. It’s a nod back to 2e priestly monks, admittedly.



This list of monk-friendly prestige classes is far from exhaustive, and I’ve completely ignored anything Pathfinder has done in this space, but thank goodness I finally got, what, sixteen years of irritation with the Shadowdancer off my chest. Seriously, for anyone who LARPs with me, it’s obviously one of my favorite character concepts, but that prestige class is juuuust about useless. There aren’t many monk-friendly prestige classes overall. Dipping my toe (reluctantly) into the waters of 3.5 monk character optimization, it looks like the community consensus on the best monk options are to weld together a bunch of other classes and prestige classes to get a better outcome.

I’m obscurely pleased to see that two of the four prestige classes in this article are already well-supported by monastic traditions in official releases – the Way of Shadow and the Way of the Sun Soul. (There was an actual Sun Soul prestige class in City of Splendors: Waterdeep, but I’m not covering it today except to say that it’s super close to just being a Way of the Four Elements monk who only buys fire disciplines, so I’ll consider that concept covered in two different ways.) The Drunken Master has seen UA support, even if we don’t yet know whether to look for it in Xanathar’s Guide to Everything. That leaves only the Tattooed Monk, which… is close enough to the beast-themed monastic tradition I’m still working on that I’m thrilled WotC hasn’t covered it yet!