I have always been a huge fan of D&D-style derivatives, but I have never actually played D&D itself. (Baldur's Gate (I & II), Final Fantasy VII+, Magic the Gathering, Oblivion, Fallout 3+).

My friends have convinced me to play my first campaign with them (I don't know much more than that), I told them I wanted run-of-the-mill D&D (3.5), no cheesy gimmicks when possible. (I want it to be hard)

I know this is a very open question, with a few parts, so try not to blow up at me after the first sentence (I am only 1/5 through the 3.5 core "manual"):

What are some general character genres that might be typically reserved for mid-high level veterans?

I want a D&D character that is going to give me a hard time, but can achieve functional synergy if played correctly. I don't want the strongest class, or the most brokenly powerful . I am looking for something that requires careful balance and tactical execution. Doesn't need to be fun (the harder I have to work, the more fun I have).

After overviewing the manuals, my attention is first drawn to Bards and Rogues. But I start getting lost in the specialization/multiclassing decisions. And while I'm sure I could mash together a crippled Thief/Bard on my own, I don't want to be an jerk to the other guys.

  • I like sneaking
  • I like traps/poisons/buffing/debuffing
  • I like micro-managing my strategy and execution at all times

My favorite playthough in Fallout: New Vegas was: sneak, unarmed, and explosives (with lockpicking and science as minors). I ran around naked with a backpack full of mines and a handful of grenades. (even then it was still easier than I had hoped, even with a difficulty modpack!).

My last playthrough of Skyrim was: sneak, alteration/conjuration, and alchemy (with minors in destruction and daggers). Ran slim on armor (so I could swing my dagger while quickly running backwards), using glyphs and summoned creatures to stage my ambushes. Boss battles would require crazy amounts Master Health Regen and Master Magic Regen.

Neither of the previous descriptions were particularly powerful, and in the hands of most casual gamers would have led to many rage-quits (only because a winning synergy took more patience and discipline than they were willing to put forth).

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    \$\begingroup\$ Have you talked to the DM and group about your character ideas? Their response is more important than ours. \$\endgroup\$
    – okeefe
    Commented Mar 19, 2014 at 18:24
  • \$\begingroup\$ Edition is updated (3.5) The DM (and group) seem to be fairly open. They tell me to find where I want, and then they will work around me (and probably hold me up to some degree). I think they are letting me determine game type. They are trying to get me hooked right off the bat :) \$\endgroup\$ Commented Mar 19, 2014 at 19:12

9 Answers 9


OK, so the artificer is the most complicated class in the game and you probably don’t want to play it. The wizard is definitely complicated, and with the right tack can do the things you’re interested in, but it’s possibly overpowered plus doesn’t really seem to have the imagery you want out of the box.

Enter the Beguiler

The beguiler from Player’s Handbook II is not as complicated as the wizard. Rather than maintaining an ever-expanding spellbook and preparing spells every morning, the beguiler just knows every spell on his spell list, and can use them in any combination he likes provided he’s still got spell slots left for the day. And ultimately, the beguiler’s not nearly as powerful.

On the other hand, the beguiler is far more obviously stealth-oriented. They have Hide and Move Silently as class skills, they can wear light armor, and they get bonuses for surprising people with their spells. Their spell list is quite good, with lots of different options, including an incredibly flexible array of illusions.1 Their 6+Int skills mean they are quite likely to have solid mundane skills for sneaking about and slipping into places they shouldn’t be.

I recommend considering the Master of Poisons and Poison Spell feats (both from Drow of the Underdark) to excel with poisons. I recommend against actually playing a drow, though, master poisoners though they are, because the LA +2 is very, very bad.

Also, the mindbender prestige class from Complete Arcane, though generally quite poor, is an amazing choice for a beguiler to take for a single level at 6th (i.e. 5th-level beguiler/1st-level mindbender). The entry is easy, and mindbender improves your spellcasting while giving you telepathy out to 100 ft., which qualifies you for the excellent Mindsight feat (Lords of Madness). Now you know exactly where every thinking mind in 100 ft. is, and that’s awesome. Continue taking beguiler levels thereafter (i.e. 5th-level beguiler/1st-level mindbender/beguiler +x)

  1. Just how flexible and useful illusions are does depend a fair bit on the DM, so you should ask about that before making a character focused on them, but in my experience most DMs are willing to let them go pretty far.

Double Jeopardy

OK, so maybe the beguiler sounds pretty cool and all, but you actually liked the way that wizard was sounding. No problem: the ultimate magus prestige class from Complete Mage is an excellent option, and nothing works so well for it as the beguiler does. Start out as a 1st-level beguiler for the sweet, sweet 4×(6+Int) skill points, and then multiclass into wizard for three levels in order to qualify for ultimate magus. Ultimate magus will improve both beguiler and wizard spellcasting. Make sure to take Practiced Spellcaster (beguiler) before you start; Practiced Spellcaster is also from Complete Mage. Being an illumian and taking the Power Sigil (Krau) feat, both from Races of Destiny, is also highly recommended.

In this approach, being a specialist wizard banning Enchantment and Illusion is a good idea because beguiler is very strong in both of those schools, so you won’t miss those spells as much. Conjuration or Transmutation are probably your best bets for specialty, though really anything can work. Practiced Spellcaster (beguiler) is a must and Power Sigil (Krau) is highly recommended, but aside from that you can still take Master of Poisons and Poison Spell. If you are a human subrace—and illumians are—, also consider Able Learner to allow you to more easily maintain your ranks in Hide and Move Silently.

  • 2
    \$\begingroup\$ Maybe missing a mention of how stealth, illusions and to a lesser part enchantments can be strongly dm dependent... \$\endgroup\$
    – Mala
    Commented Mar 19, 2014 at 22:12
  • \$\begingroup\$ @KRyan - After playing several sessions as an epic wizard (which is very very fun), we started fresh and I went with Beguiler, and it hits the spot very nicely. Ive lost interest in poison, replaced by my craze for illusion mastery and metamagics (for now at least). If I end up having to re-roll my PC, I might try splashing conjuration according to your "Double Jeopardy". Thanks much. \$\endgroup\$ Commented May 7, 2014 at 16:13

The most complicated base class, bar none, is the artificer (Eberron Campaign Setting). I like to say that the first step to playing an optimal artificer is to become a Certified Public Accountant...

The artificer is all about making magic items. That means that he has to manage his money, his time, and his XP (which is part of the cost of making magic items). He has to track which Item Creation feats he does or doesn’t have, what features do or do not apply to the construction of any given item, and to be played well, he needs a basically encyclopedic knowledge of 3.5’s best and most effective items. Because item creation takes considerably more time than preparing a spell, he needs excellent skills at anticipating the party’s needs, and where possible he needs to invest in skills and magic for reconnaissance to improve his odds of actually being able to do so.

But the artificer doesn’t stop there, oh no! Even after you’ve mastered the pros and cons of every item in the game, and even after you’ve come up with some solution for tracking all of the money and XP you are or are not spending on any given item, he also has his own version of spells, called infusions. Most of these take a long time to cast, many of them cost money or XP, and he needs to know, at any given moment, what his options are: which spells can he use quickly enough to complete mid-combat? which does he need expensive reagents for? how much reagent does he have left? Used well, these infusions are massively powerful, but unless you can track all of them efficiently, you’re very likely to waste them. Oh, and the artificer knows every single infusion published, which means if you really want to take the best advantage, you need to scour every Eberron book for infusions to make sure you really consider all your options.

But done well, the artificer is quite-possibly the most powerful class in the game. Top five, without a doubt.

Too long, didn’t read:

Don’t play an artificer.

  • \$\begingroup\$ Lol. Actually sounds kinda fun. I don't think I will attempt it anytime soon, but I am very excited to know that character complexity can go that deep \$\endgroup\$ Commented Mar 19, 2014 at 20:53
  • \$\begingroup\$ Why would someone upvote this? It's literally a negative answer, I was just reacting to the request for complexity. \$\endgroup\$
    – KRyan
    Commented Mar 19, 2014 at 20:55
  • 3
    \$\begingroup\$ @KRyan You do tell him not to play it, and show him why his request for complexity was unknowingly absolutely not what a newbie should want. (That said I haven't decided how to vote on it myself get) \$\endgroup\$ Commented Mar 19, 2014 at 21:53

Play a wizard. They can be incredibly powerful, but only if you play them with smarts.

  • I like sneaking

    Ok, play a wizard, they generally do not wear armor = no penalties to stealth. When you do not want to be seen, use invisibility.

  • I like traps/poisons/buffing/debuffing

    Ok. Wizard can do that with magic.

  • I like micro-managing my strategy and execution at all times

    Ok. Correct preparation and execution of spells is critical for wizards. You will not be a one trick pony like many other classes end up being.

  • \$\begingroup\$ Wizard is definitely a complex class, and definitely can do all of these things, and it isn’t the artificer, so this is an obvious +1 from me. \$\endgroup\$
    – KRyan
    Commented Mar 19, 2014 at 20:27
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    \$\begingroup\$ That said, I think this answer would be greatly improved by more information on how to make a sneaking wizard. They are not geared for it by default, though they absolutely can do it. \$\endgroup\$
    – KRyan
    Commented Mar 19, 2014 at 21:02

I've never suggested anyone play one, yet it it fits, so...

Play an Incarnate or Totemist

Magic of Incarnum introduces a magic system called meldshaping, wherein the users--incarnates and totemists (even Incarnum's fans admit the soulborn's lame)--channel the souls of the unborn into themselves to create blue weapons and blue armor give themselves blue superpowers.

I kid you not. Blue. Feel the power.

It's also the most fiddly, convoluted system in Dungeons and Dragons 3.5. @KRyan has explained at length about the number of things an artificer must manage--which is, I admit, totally, like, a lot--but the incarnate (the semi-wizard-like meldshaper) and totemist (the semi-sorcerer-like meldshaper) take a batch of stuff you need to know to run your character and add the ability to modify a lot of that stuff every day a lot then every round a little more. It's an absolute pain, and you'll probably love it. A starting guide to meldshaping is available here.

It won't be as versatile or as powerful as an artificer, wizard, or a cleric with access to every spell in every book--obviously--but the system is deep, complex, and rewards mastery. After gazing at it so long, you will be intimately familiar with your own navel after only a handful of sessions.

Magic of Incarnum's incarnate and totemist are the detail-oriented micromanager's dreams.

  • 1
    \$\begingroup\$ Managing soulmelds isn’t that hard, particularly if you have a useful resource for organizing them and explaining meldshaping (i.e. not Magic of Incarnum). Really, the system isn’t bad – actually, I rather love it – but the book is pretty terrible. It’s extremely poorly organized and a lot of the rules are explained in a way that makes them very difficult to grasp. \$\endgroup\$
    – KRyan
    Commented Mar 20, 2014 at 1:14
  • 1
    \$\begingroup\$ @KRyan It isn't hard, but it has a lot of moving parts, and determining how those parts fit together is both a challenge and a reward. It's the Porsche of magicians, rewarding those who know what it can do, punishing those who don't, and requiring constant maintenance. For some--like, I think, the asker--that's an awesome combination. \$\endgroup\$ Commented Mar 20, 2014 at 5:30

But I start getting lost in the specialization/multiclassing decisions.

If you're looking to be a fancy character in 3.5, you want to work backwards. Find out what the expected max level of the campaign is going to be (and if the DM doesn't know, just pick 14 or 16), find your fancy-pants prestige class (because all 3.5 builds lead to a prestige class of some sort), and then work backwards to figure out what multiclassing and skills and feats and whatnot you need to take to get there. That's your build.

In general, I'd say anything spellcasting is more complicated than any non-caster class. But to add to KRyan's note about artificers, if you're looking for something that will make your brain hurt, go fighter, go grapple, and for the love of all things d20, figure out those rules so your DM doesn't have to. :)

  • \$\begingroup\$ Fighters are shockingly complicated to build well, and of course the grapple rules are a nightmare, but ultimately they aren't very tactical. Also, prestige classes aren't always the best bet; in core, bards, clerics, and druids are best off single-classed (sorcerer makes a good argument for it too, though the archmage is worth considering). In fact, druids are almost always best off single-classed (planar shepherd, if available, would be the sole exception). \$\endgroup\$
    – KRyan
    Commented Mar 19, 2014 at 21:01
  • \$\begingroup\$ @KRyan I'll agree that the casters are generally better-served single-class, but you don't have to stray too far into the splat-books to find caster-friendly prestiges. Radiant Servant for clerics, for example, is pretty much just Cleric+. \$\endgroup\$ Commented Mar 19, 2014 at 22:25
  • \$\begingroup\$ Eh, Radiant Servant also doesn’t give much, and requires a pair of fairly poor Domains. And nothing (save planar shepherd) fully advances animal companion, spellcasting, and wild shape, so a druid always gives up something. (That said, I don’t find this answer downvote-worthy; that wasn’t me.) \$\endgroup\$
    – KRyan
    Commented Mar 20, 2014 at 1:10

First off: I completely agree with the sentiment, that you should consult the rest of your grp regarding their preferences, as well as some more specific information on the campaign as well as the other characters in your grp.

As to your character. You specify - complexity - stealth - difficulty

Difficulty mostly comes from the outside i.e. the terrain, the game and the game master. I wouldn't suggest "gimping" your character-build on purpose. Rather I'd suggest adjusting your playstyle by entertaining some ingame notions that make the game "harder" for you. For example try playing the character as a very curious person, ignoring possible risks if something he is very interested in is near or in the case of a sneaky character invent some eloborate maneuvers he wants to go through with... like luring ppl to a certain trap you have built, or something of the sort. I'm sure you get my drift.

As to possible builds and/or classes. Wizard and beguiler have both been suggested and seem well suited to your requirements. I'd add the PrC of the arcane trickster, which combines arcane spellcasting with roguish flair as well as the Factotum which is effectively a mix of a rogue and a scholar with very interesting and fun class features.


Since you like sneaking and had your eye drawn to the Rogue, I'm going to look at a few ideas that start with Rogue and add other things for complexity & features (like better sneaking).

Unseen Seer

One of my favorite ones is Unseen Seer (Complete Mage), which is basically a Rogue and a Wizard put together. There's several ways to get entry to it, though due to the skill requirements a simple one is to take Rogue at level 1 to get your skill requirements jump started, and then take Wizard after that. (Another one is to just take all Wizard and the Able Learner feat, which helps you get the necessary skills as a Wizard.)

Unseen Seer itself is a fun mix of Rogue and Wizard. You get high skill points, a lot of class skills, sneak attack (like a Rogue), and full spellcasting (like a Wizard). You also at certain levels get to pick a spell that's not on the Wizard spell list and add it to yours, which depending on your selection can let you do some really handy things. (I'm partial to the Cleric spell Divine Insight since it's virtually an "I Win" on a skill check, but there's lots of options.)

With those skill points and class skills, you get enough skill points to do things like boost your Hide. With the spells you get, you can cast things like Invisibility to become a lot more sneaky. It gives you a lot of options, including for the times you want to get behind something and stab it.

(A somewhat similar idea is the Daggerspell Mage, which is somewhat more dagger combat oriented but still gives you 9/10 spell progression.)

A Shadowdancer & Swordsage Combo

My wife is currently playing a Rogue in my game with a level of Fighter, four levels in Shadowdancer, and a level of Swordsage. It's a pretty weird build that required a lot of feats to make work, but now it's given her a lot of combat options.

  • Rogue: Grants sneak attack, and a lot of skill points. Those went into (among other things) Hide, Move Silently, Tumble, and Use Magic Device. That lets her sneak around the battlefield, avoid ops to go around (or through) enemies to set up sneak attacks, and pull out a wand or scroll as needed.
  • Fighter: Bonus feat, and martial weapon proficiency (which she's not using).
  • Shadowdancer: This class has some ugly prerequisite feats to get in. That said, it gives Hide In Plain Sight, which massively boosts the usefulness of Hide. Normally you can't use Hide while being observed, but Shadowdancer HIPS lets you use it anywhere there's a shadow near you. Underground when the Cleric is carrying a light source, that is a very easy requirement to meet. It also grants Darkvision, ability to create illusions, ability to walk through shadows, and a Shadow minion.
  • Swordsage: This grants martial stances and maneuvers from the Tome of Battle book, which are kind of like spells only for martial classes. There's some argument over how the rules work when you take a one level "dip" at higher character levels as to which level of maneuvers you can take, but we went with the multiclass chart ruling on that. So she gained once per combat abilities to do things like attack at range for 5d6 and teleporting 50 feet. She also gained a stance which adds 2d6 sneak attack dice all the time.

The net result of all of that is that she is very sneaky, has a pretty solid sneak attack dice pool, and can be very mobile in combat. She's been able to sneak up on enemy spellcasters (Hide In Plain Sight is not defeated by things like Invisibility Purge, you need to do a Spot and beat her jacked Hide) and then catch them flat footed with sneak attacks. She can also do it on the first turn of a combat at range with her Swordsage Shadow Garrote. Then she can flip back across the map and toss an emergency heal on a party member using a wand.

The only thing she can't really do is stand toe to toe with something for very long, but with her ability to use Hide fairly reliably (and a giant melee Cleric in the party!) she doesn't have to. She steps in, does big damage, and disappears.

(This one will incur multiclass XP penalties because of the class choices, if you have that. Most of the games I play in don't enforce that, but it's something to be aware of. You could drop the level of Fighter to avoid the penalty, but it'll leave you pretty feat hungry.)


Sneaking, stealth, micromanaging, and poisons? Traps and trickery? Well...

The Core Option

Bard. Bard bard bard bard bard. Bard. Bard. People think Bard is about the Inspire Courage. They could not be more wrong.

You can fascinate unwary foes, your spell list is an unending paean to trickery and illusion, you have suggestion as a class ability, and most importantly - Hide, Move Silently, Bluff, Sense Motive, and Diplomacy are all class skills. Manipulation is your GAME. Perform: Oratory or Perform: Acting are both legit targets for your perform based abilities, and Inspire Courage lasts for 5 rounds after you activate it - yell some encouragement to your friends, and then charge into battle (or shoot arrows, or cast spells, as you please).

Don't be afraid to hijack NPCs with canny skill checks or Charm Person - that's why the DM put them there, for you to use for your benefit. Walk them into traps, have them reveal secrets, provide you aid, or just lie outrageously to get free stuff.

Consider a Neutral or Evil alignment - being a manipulative and nasty bard is incredibly fun to play, and you, more than anyone, are equipped to keep that sort of wrongdoing from the party paladin (assuming you find a way around Detect Evil - Nondetection or Undetectable Alignment are a good bet).

As a canny bard, the world is your oyster - unlike the rogue, you don't need to rush into combat to be useful, and your spells just get better and better as time goes on, without the overpowering utility of the wizard or the sorcerer. You're the Joker, and every chumpy monster is your not-quite-Batman.

Non-Core Options

Beguiler has been mentioned and it is very fun to play. It's like a Bard, but with 9th level spells and less crazy musical goodness.

Song of the White Raven is a feat from Tome of Battle, Book of Nine Swords. It's the key feat for the Bardblade, a Bard who takes a level in Warblade to get some maneuvers and qualify for the feat, which gives you the ability to start your inspire courage as a swift action. Song of the Heart, another feat, from Eberron, gives Inspire Courage a +1 to hit and damage, and there's a magic item and a spell to boost it further - giving a beastly bonus to your melee and archery can really turn the tide, or turn a bunch of commoner militia from monster-fodder into a deadly hailstorm of arrows.

Swordsage, also from Tome of Battle, gives you access to lots of sneaky swordfighting tricks, especially the Shadow Hand school combined with the Shadow Blade feat. It's a more 'martial' bent, but the maneuvers and their use keeps you on your toes.

Binder, from Tome of Magic, is another interesting choice. With the Improved Binding feat, even at first level you can bind 2nd level vestiges like Malphas (invisibility, bird scout, sudden strike damage) and at 3rd you get things like Paimon (+4 dex, dance through foes hitting them all, proficiency with rapiers) or Andromalius (steal. everything.). With the Expel Vestige feat, you can change out who you are bound to depending on the situation, grabbing abilities like fire breath, aura of sadness, maddening screams, super plate armour, ally teleportation, as and when you need them. An interesting and fun combination is Swordsage and Binder, for a dex focused problem solver and warrior.

There are lots of other options, but basically:

If you want power, go for a full casting class.

If you want sneaky stabbiness, go Rogue, Ninja, or a multiclass involving swordsage.

If you want to be a silver-tongued devil, go Bard or Beguiler.

If you want to mess around with poisons, traps, and lots of options and resources, pick up Use Magic Device and lots of wands and mundane items. For the X-TREME version of this, play an Artificer.

Or mix and match from all of the above!


Start with a good story concept.

Yeah, sounds cliche, but you want to play and develop a character that you're going to enjoy playing with (and HATE losing) a year from now. In the example to follow, I started with an old drunkard who lost his wife to goblins when he was a grunt soldier, survived the war, and then with his young daughter became a drunken recluse farmer whose daughter eventually ran away. When the story started he was recalled to duty and because I had a kick-ass DM... the daughter became a powerful adversary.

Dual-or-Triple Class

One of the most versatile characters I ever played was a triple-classed rog/war/warmage. Obviously this depends heavily on what level your DM is starting you out at, in my case it was 3rd level.

How I think this combo meets your needs:

  • I like sneaking

Rogue gets you there, clearly. I invested most heavily in feats that promoted sneak attacks: Feint was my #1 weapon. I'll always give up an attack for a nearly guaranteed hit. Stabby stabby? STABBY STABBY!

  • I like traps/poisons/buffing/debuffing

If you're willing to invest the up-front effort to develop a 3/2/1 war/rog/warmage, you'll actually find that the synergy you get with war/rog gives you a ton of physical tactical options. I admit, the warmage spell list is quite light on buffs/debuffs. But you seem to like being a support character, and I can say that the tactical options I had with this triple-class was insane. Once I was 3/2/1 I did pure warmage until he was 3/2/6. Few things are as nasty as a surprise fireball. Between war/rog I kept towards skills to get dual wielding and then used feint to flat-foot close-range opponents and then slice and dice with backstabs.

Better yet, in a jam, he could actually physically defend himself!

  • I like micro-managing my strategy and execution at all times

In 3.5, wizard type classes are horribly underpowered early on. With 1d4 HD, death is quick. If you take the time to multiclass, you can mitigate this, and then have a baseline to safely build your magical talents. (Whatever you may choose... it certainly doesn't have to be Warmage!)

I also had good success with a combo sorcerer/rog. Since you're just starting, sorcerer might not be a terrible idea if there's already a steadfast caster. There aren't as many things to remember.


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