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My friend is going to create a character of a virtuso assassin. If I understand him correctly, he'd like to be someone with split personality. A successful, well-known musician and dancer, who becomes a ruthless cutthroat when there is need for it.

Is there a class or two that would perfectly fit into something like this? Please note, that I am interested in specific classes that grant mentioned features, not character builds. The player is quite stubborn. He has already chosen drow as race(monster class levels from Savage Species to take one gestalt's class slot), items and feats. He is not willing to change them, as he is pumping everything in Death Attack's DC while team's archivist focuses on debuffs.

Simple bard/rogue/assassin turned out to be a poor choice, because the character would be dependant on Dexterity, Intelligence and Charisma, which is too much. I couldn't find a good combination that would reduce the crucial abilities to 2. Using poisons, sneak and death attacks are a must. It would be nice if the class had charisma based death attacks or be able to use Intelligence for perform and other social tests. A few bardic features similar to fascinate would be nice, however they are not a must. It is not a problem if the mentioned features will be gained later, however if it would be 20th class level it would be a poor choice, because the character will be deprived of what they want.

Gestalt rules, character at 8th ECL.

3.0, 3.5, Dungeon Adventures and Dragon Magazines allowed.

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closed as too broad by Ernir, Oblivious Sage, Christopher, LegendaryDude, nvoigt Jun 18 '16 at 12:52

Please edit the question to limit it to a specific problem with enough detail to identify an adequate answer. Avoid asking multiple distinct questions at once. See the How to Ask page for help clarifying this question. If this question can be reworded to fit the rules in the help center, please edit the question.

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    \$\begingroup\$ Would a class that gains death attack, but later than 8th level, be acceptable? It hits a lot of thematic points and the character could work towards death attack, but it wouldn’t be available for actual use for quite a long time. Not sure if it fits. \$\endgroup\$ – KRyan Jun 16 '16 at 4:41
  • \$\begingroup\$ There is a huge amount of combinations and there is no way for us to pick the "correct" one. Can you give at least a little direction what you want? For example compared to the obvious, plain bard 8 / assassin 8, what would you want to improve? \$\endgroup\$ – nvoigt Jun 18 '16 at 12:50
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    \$\begingroup\$ So wait, if I just said “binder and bard, or factotum and black dog,” you would like my answer, but because I went into more detail in how they might be used, you don’t? That makes no sense to me. \$\endgroup\$ – KRyan Jun 18 '16 at 14:16
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    \$\begingroup\$ @Momonga-sama You requested classes that serve a purpose. Answers are required to back up their assertions, so I had to indicate what made them good choices for this purpose. If you were looking for people to literally just list class names for you to go look at, you came to the wrong place. \$\endgroup\$ – KRyan Jun 19 '16 at 23:54
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    \$\begingroup\$ If the question is just looking for people to put together lists of classes which might be good for a singing assassin, this is a list question of both the “too broad” and “opinion based” type that will stay closed. RPG.se isn't really the place to ask for others to do the research scutwork for vague ideas—not because we don't want to (somebody always wants to, often multiple somebodies), but because voting becomes meaningless. This would have to be turned into a charop question with well-specified constraints and goals in order to work here, or just asked on a discussion forum. \$\endgroup\$ – SevenSidedDie Jun 20 '16 at 1:24
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I basically see two ways to do this. The first is to go Charisma-based, knowing you’ll still probably need a fair amount of Intelligence and that death attack won’t be available until 13th. The second is to go Intelligence-based, and then rely on skill ranks and other bonuses to have decent Perform.

Either way, to use poisons you are going to need the Master of Poisons feat from Drow of the Underdark. This feat offers both poison use, and the ability to poison weapons as a swift action. And to create poisons, Craft (poisonmaking) offers a crucial ⅙-cost as long as you have access to the materials, which is massive and critical since poisons are so expensive. For the best poisons to use, I suggest perusing the Arsenic & Old Lace handbook.

Also, once you get death attack, however you get it, the Favored in Guild feat for the Jaezred Chaulsinn organization in the Dragons of Faerûn web enhancement has a pretty significant benefit to death attack DCs. The fluff requirements will likely be problematic, however.

Charisma-based—Binder/Knight of the Sacred Seal//dips/Bard

The go-to here is the binder class. The Marchosias, King of Killers vestige (available at 13th with Improved Binding) grants a Charisma-based death attack. Earlier vestiges also have high points worth considering:

  • Naberius, the Grinning Hound—excellent social skills, right from 1st.

  • Malphas, the Turnfeather—invisibility, fantastic scouting from a summonable raven, and sudden strike. Poison use, too, but you should already have Master of Poisons.

  • Andromalius, the Repentant Rogue—sneak attack is much better than sudden strike. Jester’s mirth is also a decent save-or-lose.

  • Focalor, the Prince of Tears—aura of sadness applies a −2 penalty to the attack, AC, and saves of those adjacent to you. That makes your poison and death attack far more likely to actually work.

  • Karsus, Hubris in the Blood—could use wands of minor creation and fabricate to make poisons; the duration on minor creation probably kills this as a realistic option most of the time though, since you really want to be using Focalor when applying the poison.

  • Astaroth, the Unjustly Fallen—bonuses to Craft (poisonmaking) and the ability to make the above wands as well as things like assassination and/or toxic weapons.

  • Eurynome, Mother of the Material—befriend venomous animals, get them to donate to your cause.

  • Chupoclops, Harbinger of Forever—another save-lowering aura, which stacks with Focalor’s, plus fantastic abilities for lying in wait.

In addition to being Charisma-based, the binder class revolves around forging pacts with these vestiges, which seek to gain influence over the binder. Could be very appropriate for that “split personality” concept.

The ideal case would be Chupoclops, Focalor, and Marchosias; hitting saves with a −4 penalty will do wonders for your success rate with poisons or death attack. Naberius, Karsus, and Astaroth on down days should allow you to deal with non-combat and build up a supply of poisons.

Note that the knight of the sacred seal prestige class is close to a strict upgrade to binder; if you can afford a Weapon Focus of any kind, you should probably take this class.

On the other side, bard does make the most sense: bardic music is certainly appropriate, and it qualifies you for Snowflake Wardance from Frostburn for adding Charisma to attack rolls, ideal for keeping your accuracy up. Other ideas for a bard can be found here. There are two other things to consider, however.

The first is the bard variant from Athas.org’s Dark Sun Campaign Setting—this trades the bard’s spellcasting, which is excellent, for several skill bonuses and “trade secrets.” In reality, this is a bad trade, but a few of the trade secrets interact with poisons, which makes it worth considering. Improvised materials would ensure that you always qualify for the ⅙ cost with Craft (poisonmaking), and scorpion’s touch improves poisons’ DC. Note that Dark Sun Campaign Setting was licensed by Wizards but not actually produced by them, and several things produced by Athas.org are rather questionable—the bard, though, is solid.

The second is a bit of dipping opposite binder. There are two concerns here:

  • One, you really want a non-vestige source of at least 1d6 sneak attack damage, at least by the time you get Marchosias. The Complete Adventurer spellthief is Charisma-based, and the trickster variant from Dragon vol. 353 is quite good, so that could work for a level; Master Spellthief from Compelte Scoundrel is also a pretty good feat. Godsblood Spelltheft may also be interesting.

    Alternatively, taking a level of swordsage from Tome of Battle at 9th level allows you to pick up assassin’s stance as well as a plethora of other excellent options, like mountain hammer, cloak of deception, and shadow jaunt.

  • Two, any Charisma-based character has to at least consider paladin for divine grace; +Cha to all saves is just amazing. And since harmonious knight from the Champions of Valor web enhancement grants another use of Inspire Courage at 1st, and paladin of tyranny from Unearthed Arcana grants aura of despair at 3rd, three levels of paladin is almost impossible to beat for this character. The paladin of tyranny aura of despair probably does not stack with Chupoclops’s, but you gain it massively earlier, it doesn’t take a vestige slot, and most importantly, it is not mind-affecting, as Chupoclops’s is.

Thus, I recommend something like Binder 8//Paladin 3/Bard 5, with plans to take a level of binder//swordsage at 9th. For race, strongheart halfling from Player’s Guide to Faerûn is a strong contender; small size is excellent for stealth, and the bonus feat always helps. Lesser aasimar or (venerable) dragonwrought kobold would be even better, but those are rather cheesy, so check with the table before going for those.

Intelligence-based—Factotum//dips/Black Dog/Assassin

Intelligence has a lot of advantages for this character: there are a lot more options for death attack, and a lot of the best options for creating poisons want some Intelligence. Plus, as you’ll see, we’ll be able to access substantial non-Charisma bonuses to Perform.

Factotum from Dungeonscape is the star here: it gets a little bit of everything (pretty much the “Indiana Jones in D&D” class), including excellent skills. It has Perform in-class; it has everything in-class. It can, 1/day, add its class level to Perform checks; it can do that once each per day for every skill. If you take all eight levels on one side as factotum, that’s a +8 bonus; far larger than you would have likely gotten from Charisma. It gets a little bit of sneak attack; not a lot, but enough to trigger death attack. It also gets a smattering of spell-like abilities, allowing for quick-and-cheap uses of things like minor creation and fabricate for poisons.

And, of course, at 8th level the factotum gains the ability to take an extra standard action in a round. That is huge. That alone makes factotum the best “other side” in gestalt. If you want to use this a lot, however, you will want to take Font of Inspiration several times.

On the other side, black dog from Dragonmarked is a prestige class that you can start at 6th, and gains death attack at 2nd level. It also stacks with assassin for death attack DCs. More importantly, it has some of the most potent poison-related abilities in the game. So levels 6th through 20th should probably be black dog and assassin.

Black dog requires the Least Mark of Hospitality feat from Eberron Campaign Setting, and that requires you be a halfling. If you make that a strongheart halfling from Player’s Guide to Faerûn, you get a bonus feat so it’s basically free. Strongheart halfling is a really strong race for this character no matter what you do, honestly.

Prior to gaining access to these, you have five levels. An interesting option for three of these is duskblade from Player’s Handbook II—its arcane channeling could be combined with Poison Spell from Drow of the Underdark to use one poison on, say, chill touch (Sandstorm’s parching touch might be even better, if you can convince the DM it should be on the duskblade list) to make multiple attacks with a single poison, greatly extending its use.

A level in swordsage from Tome of Battle remains useful—island of blades is honestly even better than assassin’s stance, and since there is no Intelligence analogue to Snowflake Wardance, you will want decent Dexterity and swordsage will help you qualify for Shadow Blade from the same book to make better use of it. You could even ask your DM if Kung Fu Genius from Dragon Compendium or Carmendine Monk from Champions of Valor might be houseruled to apply to swordsage, and take two levels to get Int-to-AC.

Failing that, I would probably go with a level in shaper psion or druid, just to make it easier to produce poisons. Shaper gets psionic minor creation, a 1st-level power rather than the 4th-level spell minor creation, and druid gets a (potentially venomous) animal companion and the breath of the jungle spell, which significantly reduces creatures’ saves against poison in a large area.

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So I’m going to lay out a rather unusual build for a fairly unique character. It has an emphasis on Charisma and a subtle mysticism that increases vulnerabilities and windows of opportunity.

The build ends up looking like this:

\begin{array}{l} \text{RHD} & \text{RHD} & \text{RHD} & \text{LA} & \text{Paladin} & \text{Pal 2} & \text{Pal 3} & \text{Ranger} \\ \text{Cleric} & \text{Warlock} & \text{War 2} & \text{Hexblade} & \text{Hex 2} & \text{War 3} & \text{War 4} & \text{Enlightened Spirit} \end{array}

Use of paladin of tyranny locks the character in to Lawful Evil alignment, which probably fits an assassin quite well, and that means using the adaptation for enlightened spirit to allow it to be evil. Those, along with the marrulurk race used to start this off, are the biggest questions that should be brought up with your DM.

Feats are incredibly tight, and I list far more feats as things of interest than you can actually afford to take, but the key ones are are Master of Poisons, Blend into Shadows, and Snowflake Wardance. If flaws are allowed, Extra Music and Instinctive Darkness are extremely high priorities.

The 27,000 gp worth of wealth is also being stretched thin: 8,000 gp on a lesser chasuble of fell power is compulsory. Weapons are pricey too: a feycraft short sword is 1,810 gp before adding any magic, and getting it to at least +1 is probably necessary, so that’s 3,810 gp. A +1 mithral chain shirt runs 2,100 gp, and while you don’t necessarily need it, a cloak of resistance +1 is a very good item but costs another 1,000 gp. Make it also a cloak of charisma +2 because everything you do is Charisma-based, there’s another 4,000 gp. Attempting to do dual-wielding means gloves of the balanced hand and another short sword; the money just isn’t there. A pair of hexbands is just 3,100 gp, so that’s an obvious choice. A least crystal of return on the weapon and restful crystal on the armor is another 800 gp. That leaves 4,190 gp for assorted other goodies. Probably wands of grave strike, golem strike, and maybe vine strike in wand chambers, and an enemy spirit pouch.

This character gets bardic music, Charisma to all saves twice, applies a −4 penalty to the attacks, AC, and saves of everything around him, has a Charisma-based death attack, and can apply poisons to weapons as a swift action at no risk of self-poisoning. He adds Dexterity and Charisma to attack rolls, and 5/day can add Charisma on damage rolls too. He can see in darkness, even magical darkness, and can throw around his own darkness at will.

If this character continues to level, 9th should almost-certainly be swordsage//fighter. Swordsage offers a ton of tricks of massive value to you, including the option of taking Shadow Blade, and fighter gives BAB, which you want, and feats, which you desperately need.

Below is a more detailed breakdown of what these classes are doing for us and how we end up.

Side A—the killer

In eight levels, this side offers +7 BAB (we’ll get the other one back on the other side), bardic music, sneak attack, death attack, several favored enemy bonuses, +Cha to all saves, and −2 to the attack, AC, and saving throws of those within 5 feet of you.

Marrulurk—three racial hit dice, +1 level adjustment

  • Marrulurk is from Sandstorm

This race is absurd. It’s small and gets enormous ability score bonuses (+2 Strength, +6 Dexterity, +4 Constitution, +6 Wisdom, +4 Charisma), +2d6 sneak attack damage, +4 racial bonus on Hide and Move Silently, Point-blank Shot and Rapid Shot as bonus feats, poison use, a Con-based nauseating breath weapon, and a Charisma-based death attack. The rest of it could probably be bested by a careful selection of classes, but that feature is unique and too perfect for this character. Though please note that death attack is only worth it if you can start the fight with one. Waiting around three rounds in the middle of a fight is never worth it.

Being a jackal-person might make being a famous musician a somewhat tougher sell, but if the skills are there then it shouldn’t be a problem.

If you don’t want to be a marrulurk (or the DM doesn’t want you to be), strongheart halfling (Forgotten Realms Campaign Setting) is small and gets a bonus feat à la human, which is also awesome (this character desperately needs extra feats). The RHD and LA can be replaced by four levels in bard, the variant from Dark Sun Campaign Setting if allowed (this product is licensed by Wizards, but not produced by Wizards; I won’t vouch for much of it, but the bard is quality). The lore song option from Dungeonscape is also good for this character. Don’t fall into the trap option in Drow of the Underdark for poison use, though—poison use is garbage.

Regardless of whether or not you already have poison use, the Master of Poisons feat from Drow of the Underdark is critical. It eliminates accidental self-poisoning, as poison use does, but it also allows swift-action poison application. That changes poison from a waste of time to something useful.

Aside from that, Weapon Finesse is kinda duh with that Dexterity bonus, but the feycraft item template from Dungeon Master’s Guide II allows light weapons to use Dexterity even if you lack Weapon Finesse; the money is way cheaper than a feat for you. You will also absolutely need Darkstalker from Lords of Madness eventually, though by 8th level it’s probably not critical. Keep it in mind, though.

Harmonious knight of tyranny with favored enemy—three levels

  • Paladin is a core class

Particularly for a well-known, virtuoso-style musician, I think law fits, and cutthroat and willing to kill people hits evil neatly, so I think the LE requirement here works out. Paladin of tyranny does swap detect evil for detect good while harmonious knight swaps detect evil for inspire courage, but I would guess most DMs won’t object to swapping detect good for inspire courage.

Anyway, the idea here is that harmonious knight gives inspire courage +1, 1/day at 1st level, and paladin of tyranny gives an aura of despair at 3rd level, while still gaining divine grace at 2nd level. Aura of despair reduces nearby enemies’ saving throws—e.g. against poison or against death attack.

Favored enemy is preferred over deadly touch since it aids in tracking and stealth. The paladin options for this are limited, but it also stacks neatly. You could even swap smite good for favored enemy (devils) with the holy judge variant from Champions of Valor, if your DM will allow you to be both a “holy judge” and “paladin of tyranny” (devils certainly hunt down their own kind often enough, so it’s really not that big a stretch, but worth checking). Being specific to only devils is bad, but the way favored enemy stacks when you gain more makes it still worth doing (you could have +2 to devils, and then +4 to whatever you choose with the Unearthed Arcana variant).

Important feats here are going to be Extra Music (Complete Adventurer) and Snowflake Wardance (Frostburn). Snowflake Wardance allows you to use your bardic music to add your Charisma bonus to attack rolls (stacking with Strength or Dexterity as appropriate).

Solitary arcane hunter with voice of the city—one level

  • Ranger is a core class

    • Solitary hunting is from Dragon vol. 347

    • Arcane hunter is from Complete Mage

    • Voice of the city is from the Cityscape web enhancement

After the above three levels of paladin, you have favored enemy already once or twice, and here you gain it a third time—targeting anything arcane. That’s a huge group, and in most campaigns is a better choice than any of the regular choices. But this can be campaign-dependent; some campaigns will have focuses that can make other choices better. Also keep the Unearted Arcana favored environment options in mind.

Solitary hunting makes all of your favored enemy bonuses apply to attack as well as damage, which is awesome.

Voice of the city allows you to attempt to communicate with those who you don’t share a language which. Seems far more appropriate for this character than wild empathy, though neither feature is terribly important.

Important feats here are going to be Favored Power Attack (Complete Warrior), and if you can completely ignore alignment, Nemesis (Book of Exalted Deeds).

Enemy spirit pouches are going to be critical for this to work out. This 2,100 gp item from Magic Item Compendium gives you a new favored enemy, or improves an existing one by +2. Buy several, swap them between fights as necessary.

Side B—the sneak

This side offers mobility, stealth, magic-item use, and another +Cha to all saves and −2 to the attacks, AC, and saves of those within 5 feet of you. It also offers some much-needed skill points, and a +1 BAB patch when the other side misses that.

Cloistered cleric with Travel Devotion—one level

  • Cleric is a core class

    • Cloistered cleric is from Unearthed Arcana

    • Travel Devotion, and the option for clerics to swap a domain for devotion feats, is from Complete Champion

Cloistered cleric is easily the best single level in the game, and in this case, you very much want Travel Devotion for swift-action movement. Trading the cloistered cleric’s free Knowledge Domain for Knowledge Devotion is also desirable, since you’ll have a fair few skill points and it’s a minimum +1 attack, +1 damage.

For the last domain, Luck (reroll 1/day) or Time (Improved Initiative) are always solid stand-bys, but for this character Charm (+4 Charisma for 1 minute, 1/day) or Pleasure (Book of Exalted Deeds, immunity to Charisma damage or drain) are well worth considering. I cannot best the Arsenic and Old Lace Handbook for advice on using poisons.

For feats, Lolth’s Caress from Drow of the Underdark is worth considering if allowed without actually worshiping Lolth (which you can’t do and still get Travel Devotion), though ultimately Travel Devotion is a higher priority for Rebuke Undead uses, and many other feats are higher priority than this is.

Hexblade—two levels

  • Hexblade is from Complete Warrior

Make sure at least one of these levels is opposite marrulurk’s LA, to keep your BAB up. Anyway, this gives you a Charisma-based curse, which is OK-ish since you’ll have high Charisma and be murdering people’s saving throws, and then Arcane Resistance, which is like Divine Grace but only for spells.

It is well worth considering continuing with hexblade for another two levels, to use the dark companion option in Player’s Handbook II. Because another −2 to all saves is right up this character’s alley.

The hexbands from Magic Item Compendium are valuable here.

Warlock—four levels

  • Warlock is from Complete Arcane

Warlock offers several things of note here: a 2d6-damage eldritch blast, the darkness, devil’s sight, and either beguiling influence or dark one’s own luck invocations, plus deceive item, the ability to take-10 on Use Magic Device. It would be difficult to overstate how massive that is. The eldritch blast probably doesn’t get used, but with a lesser chasuble of fell power, you get it up to 3d6—enough to take a level in enlightened spirit.

For feats, we’re once again looking at Drow of the Underdark—the darkness-related feats are awesome. Blend into Shadows turns your darkness into Hide in Plain Sight, and Instinctive Darkness lets you use it as an immediate action.

Enlightened spirit—one level

  • Enlightened spirit is from Complete Mage

This class has a Good requirement, but also has an official adaptation for Evil, if you don’t just ignore alignment altogether. It also requires a 3d6 eldritch blast—you can expect to see warlock on the other side. Anyway, beyond first, there is basically no reason to continue in the class, but the first level offers two awesome auras: of courage and of menace. Aura of courage is always nice, and aura of menace applies a −2 penalty to attacks, AC, and saves to everything next to you. That save penalty applies to your death attack and your poisons, so it is critical.

Skills

Your first level includes a 6+Int class, so you get those quadrupled. Your last level also does, but the six in between have only 2+Int, so you’ll have a few extra skill points to toss into things that require a few ranks, but you’ll only really get to maximize a few.

6 ranks of Perform (dance) is necessary for Snowflake Wardance, and Hide and Move Silently are obviously important (though you do have +8 to both from marrulurk, between its small size and racial bonuses). If you want to Inspire Courage, Perform (sing) allows you to do so without needing hands, or you can try to convince your DM that Perform (dance) should work with line of sight rather than being able to hear it.

Craft (poisonmaking) is crucial as well; when you have decent access to materials, Craft (poisonmaking) works at ⅙ the base price of the poison. Poisons are expensive, and skill ranks are generally cheap, so make it happen.

And Concentration is necessary to use your darkness ability in close quarters, and will be useful if you do take levels in swordsage in the future and pick up some Diamond Mind manuevers (emerald razor, ruby/sapphire/diamond nightmare blade, etc.).

Finally, you get to take-10 on Use Magic Device, and are looking to have a huge Charisma. Enough ranks in UMD to get the +10 bonus necessary to hit DC 20 for a wand while taking-10 is something you absolutely should do.

If you have more points, 5 ranks in Balance prevents you from being flat-footed by balancing, which is really nice. A rank in things like Knowledge, Sleight of Hand, and Tumble allows you to do things you otherwise couldn’t—in fact, if you can afford it, maxing Tumble is well worth it.

Items

As mentioned, lesser chasuble of fell power (Complete Arcane) is required. Cloak of charisma is obvious, and can be combined at no extra cost (Magic Item Compendium) with a cloak of resistance, which is less important considering your save bonuses but it would be silly to ignore the option.

Weapon should be a pair of feycraft short swords (Dungeon Master’s Guide II); feycraft allows you to use them as if you had Weapon Finesse. Need to be at least +1 for piercing DR/magic. Attach least crystals of return to these to allow them to be drawn as a free action. Armor is standard mithral chain shirt; a restful crystal allows you to sleep in it at no penalty.

Gloves of the balanced hand (Magic Item Compendium) grant Two-Weapon Fighting, hexbands (Magic Item Compendium) add Charisma to damage against a cursed target 5/day, and gauntlets of heartfelt blows (Dragon Compendium) add fire damage equal to Charisma. Combining gloves of the balanced hand and gauntlets of heartfelt blows makes the gloves cost 50% more, so the combo would be 24,000 gp. Late-game, slippers of battledancing (Dungeon Master’s Guide II) add Charisma to attack and damage again, so that will someday be worth it.

This character will have excellent Use Magic Device, so wands are good ideas. Golem strike, grave strike, and vine strike are each from Spell Compendium, and are 1st-level spells that allow you to sneak attack things that are ordinarily immune to it. You want these, because death attack relies on sneak attack. Dungeonscape has rules for wand chambers, so you can hide these wands about your person without having to hold them.

Finally, enemy spirit pouches can give you more options for favored enemy. This is very nice.

Past 8th level

Swordsage from Tome of Battle has so much to offer at 9th that it’s nearly must-have at this point. You can take island of blades or assassin’s stance, and pick up things like mountain hammer, cloak of deception, shadow jaunt, and emerald razor.

On the other side, you want to keep your BAB up and you desperately need feats: that spells fighter to me. Drow of the Underdark has the excellent hit-n-run tactics variant, which gets +2 to initiative and Dex-to-damage vs. flat-footed targets (which most will be thanks to your darkness).

Feats should emphasize picking up things you haven’t managed to fit in yet, plus the new option of Shadow Blade for Dex-to-damage. Extra Music, Power Attack, Favored Power Attack, any missing darkness feats, etc. are all strong contenders. Nemesis, if ignoring alignment restrictions.

From there, another level of fighter is probably desirable; might even want to double-down on the topic and go with psychic warrior on the other side, for two feats (assuming your DM allows that in gestalt). Psychic warrior also adds the option of taking Expanded Knowledge for psionic creation to make poisons that way. Two more levels of hexblade get the excellent dark companion, for another aura of save-reduction, this one that you can move independently of yourself. Binder levels would allow you to access Naberius, the Grinning Hound and potentially Focalor, the Prince of Tears. Naberius offers substantial social skills, while Focalor’s aura of sadness is another save-reducing aura.

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  • \$\begingroup\$ Protip, if for some reason your DM disallows paladin of tyranny variation, you can still get similar effects via Blackguard prestige class. My DM hated the variant paladins, but allowed blackguard since you had to "prove yourself" to earn the evil paladin benefits. Great build concept though. \$\endgroup\$ – Drew Major Jun 14 '16 at 20:23
  • \$\begingroup\$ @DrewMajor True, but unfortunately the feat requirements are brutal there. \$\endgroup\$ – KRyan Jun 14 '16 at 20:38
  • \$\begingroup\$ The question was about a class/classes with abilities similar to assassin like poison use, sneak attacks, death attacks etc. What you posted is a build with lots of level dips without actually answering the question. \$\endgroup\$ – Momonga-sama Jun 15 '16 at 19:31
  • \$\begingroup\$ @Momonga-sama I see. I would argue that, in presenting a build, I have also suggested a number of classes, but if the goal is something simpler and/or more modular, I may have some ideas. \$\endgroup\$ – KRyan Jun 15 '16 at 23:55
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Gestalt rules and Dragon Magazine lead to a plethora of choices. http://brilliantgameologists.com/boards/index.php?topic=4854.0 <--The Poison Handbook is a solid place to start.

I'm not personally very experienced with Gestalt, so my advice there is limited. However, I have built a wide variety of NPCs for an Eberron game focusing on the war between the Houses of Shadow (Both of which have magical assassination and great performance as their MO).

The Drow Bard (From, unsurprisingly enough, Drow of the Underdark) is not actually limited to Drow only, just exemplified by them, and gains Poison Use at level 1.

It's also worth noting that one can be an exemplary Performer without any Bard levels at all, so long as you have perform as a class skill, and a reasonable charisma. An assassin, Unseen Seer, or arcane trickster, particularly with a sorcerer base for the last two, could be an amazing Performer.

Death Attack is a somewhat rarer ability, and to the best of my knowledge, can be obtained by a handful of classes. Of particular interest might be binder, which is one of the few ways to get a death attack that is not intelligence based. (It is charisma based).

For a smooth talking, high performance check, murdering assassin, I would probably lean towards something like a rogue//binder in gestalt. Use Naberius, Focalar, Marchosias. Perhaps Chupoclops to get the three rounds you need for a death attack). It's not as high powered as some gestalt combinations, but it has flavor for miles, and should be reasonably effective. Additionally, should you find yourself in a situation where both death attack and Poison are useless (say, fighting undead) the Binder has the option to bind different vestiges and still be useful.

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  • \$\begingroup\$ Drow bard is actually a trap; to use poisons, you need the Master of Poisons feat (for its swift-action application), but that feat also covers poison use, making actually having poison use redundant. Losing bardic music uses isn’t worth it. Too many good suggestions here for me to actually downvote for that, but it is keeping me from upvoting. \$\endgroup\$ – KRyan Jun 14 '16 at 17:46
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I propose the following split personality: your character is friendly and helpful while visible but turns murderous when invisible.

Then, combine a spell casting class (sorcerer?) with the rogue and assassin classes. In combat, use greater invisibility and sneak attack like crazy.

The rogue class will give you all the perform skill ranks you need to be a good singer. Note that spells such as minor image can create sound which could be more impressive than your unsegmented singing voice.

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If it suits you, you might consider these two options:

1. Default Classes

Yeees. I think character that you described can be modeled out of box with any of default classes. I mean, really, just think about it:

If we approach his 'art' side from identifying classes that focus on 'Performance' - here are the ones that has Performance as Class Skill: Bard, Monk, Rogue. I think Monk doesn't have any traction with your character. I don't think that you really need Bard. In my opinion, Rogue can model your character just fine. As for skills he has to take skills at

  • Performance - to be virtuoso in singing you need those ^ ^

  • Craft (alchemy) or Craft(poisons) (depending on your GM judgement what is proper here) will let character into the world of poisons. Other skills are up to player and amount of intelligence points.

As for abilities - I assume Charisma should take some love (it rings well with character for +2 +3 or +4 ), Dexterity too.

I assume that even 1st level character can be awesome at some skill from the in-rpg-world point of view. Even more so if you take feat Skill Focus = +3 to Skill. So you could take that for Performance.

You can also look in direction of any class that doesn't have performance among preferred skills. Skill Focus+3 + high Charisma can explain why your character is virtuoso. ^ ^ Most logical 'non-performer' for me is Fighter class - for good or ill.

If you think about Prestige Classes in the future (first DMG 3.5) - in my opinion, Duelist looks somewhat fitting for popstar-asassin but it has strict requirements for 3 combat feat - Dodge, Mobility, Weapon Finesse.

Assassin Prestige Class has Death attacks and poisons but it looks goofy and requires a lot of XP. Why make things complex and wait so long, huh?

As for Death attacks - you might consider poisons, ACID, artifacts.

2. Dark Sun bards

Yet if default classes don't work for you, then maybe you could find interesting one nontrivial option of a non-Dragon-Magazine class Athasian Bard. To give a context - those are the bards from Dark Sun setting, but what' relevant here those correlate to your concept very close. In by opinion those are interesting both from role-playing perspective (

  • They entertain nobles.
  • They kill nobles.
  • Because other nobles pay them to entertain and/or kill other nobles.
  • This is part of noble's games.
  • And those bards make poisons.
  • And they sell those to make living
  • And they hoard knowledge not distribute it
  • Common folk canэе distinguish them from rogues or the guise that bard uses.

) and with from amount of opportunities + tools they provide to interact with the game world. Being different from vanilla bards, they have no arcane magic but they can have a lot of interesting and believable rogue-ish abilities and yes, poison there is ^ ^ if you commit to it then a lot. Here you can find online premier: http://dfds.wikia.com/wiki/Athasian_Bard You can find conversion to 3.0 which is closer to being official here: http://athas.org/products/ds3

Personally I thought that Dark Sun setting is dead but, it seems not Hey I Can Chan (many kudos to him/her) mentioned that although some Dragon and Dungeon magazines updated to 3.5 some Dark Sun setting stuff, the much of the setting (including the Athasian bard with poison use) was also updated and made available for free at Athas.org, like the main ebook. While not published by Wizards of the Coast, the site was allowed via a special Wizards' license, to continue producing material for the Dark Sun setting.

So, personally I think you could judge that as somewhat official class ^ ^

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