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:
| 1st |
2nd |
3rd |
4th |
5th |
6th |
7th |
8th |
| RHD |
RHD |
RHD |
LA |
Paladin |
Pal 2 |
Pal 3 |
Ranger |
| Cleric |
Warlock |
War 2 |
Hexblade |
Hex 2 |
War 3 |
War 4 |
Enlightened Spirit |
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
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.