Help me build a sadistic monk/cleric or bard/warlock

[Mongrel]

Hey guys! You may remember me from my recent thread asking for help on building my Conquistador-themed character (http://www.giantitp.com/forums/showthread.php?549638-Prestige-class-for-my-Conquistador) for an "explore the new world" type game with evil alignment encouraged. Well, as the most senior player in that game, I've been tasked with helping some of the other players build their characters. We've all played at least some 3.x DnD before but the other players aren't very well-versed in the rules, and I've been playing 5th edition long enough to be rusty.

One of the players wants to play a sadistic character who derives pleasure from harming others, enjoying hurting people then healing them to keep them alive. He's said that he'd like the character to be a cleric/wizard, cleric/druid, cleric/monk, or bard/warlock, but is leaning towards cleric/monk or bard/warlock. I'm thinking he'd make a good torturemaster/interrogator for the party.

To me, bard/warlock seems like the more interesting path, since I don't think I've ever seen someone play that combo before (and "musician who made a deal with the devil" just seems cool to me lol), though cleric/monk is probably the easiest to build; I figure I'd just put him on the path to Sacred Fist, although that does allow for less flexibility to choose flavor-appropriate feats and whatnot.

We start at level 3 for this game. The DM is fairly lenient with character creation, and tends to allow most content (splatbooks, third party stuff, even homebrew) and waive alignment restrictions on classes and stuff like that. We're also not powergamers in our group, so a feat or class with flavorful character-appropriate abilities would be preferable to whatever hyper-optimized build might exist (in fact it's probably best if the character isn't absurdly powerful). Furthermore, don't get too hung up on the class specifications. I think if I can build a character that fits the "sadistic spellcaster who can heal" mold the player will be happy even if it isn't necessarily a cleric/monk or bard/warlock.

So far I've uncovered the Sadistic Reward feat from Drow of the Underdark and the Sadist spell from BovD, which each seem pretty appropriate for the character. The Pain Touch feat from Complete Warrior also seems pretty good for a chara with monk levels. What other feats or spells would be good for this guy? And, perhaps more importantly, what would you guys recommend as far as class(es)?

[skunk3]

What about a cleric/warlock? (Eldritch Disciple.) I am playing one now and it's really fun!

[Falontani]

Eldritch Theurge from Complete Mage is a bard warlock prestige class. You can add spells from your bard list with a target to an eldritch blast. So you could cast an eldritch blast with Power Word Pain attached to it, or a blast with a cure spell attached to it.
If you are entirely going for thematic rather than power, then I would suggest several of the vile spells from Book of Vile Darkness, however those spells can not be taken on a spontaneous spellcaster like Bard without a feat from Heroes of Horror: Corrupt Arcana, or the feat Arcane Preparation from Complete Arcane.

Some other things to look into:
Haunting Melody from Eberron Campaign Setting, its a fairly worthless ability, but you can use your bardic music to inspire fear
Inspire Hatred from Exemplars of Evil, its a song that can make several different people go into an uncontrollable fury that forces them to attack a creature of your choice

Finally if you want to play with the dead with all this you can take Dirgesinger, a prestige class that gets several cool abilities and can eventually raise the dead while performing, which while others can do it better, it is an utterly horrifying thought since they can do it as simply as starting a bard song.
That is all without mentioning the plethora of things a warlock can do innately.


What about a cleric/warlock? (Eldritch Disciple.) I am playing one now and it's really fun!
I was actually looking at that one because if your deity is chaotic you can use your eldritch blast to heal, but it requires your deity to be chaotic and not evil, meaning you couldn't use magic like Liquid Pain without losing access to the fun of that ability

[Noldoran]

It's kind of important to note that the monk is not a great class. The two easiest ways to ramp it up are through fast spellcasting and/or size increases. An Evil way to power up the monk a bit would be the Willing Deformity (Tall) feat, from the BoVD. It gives +5 reach, which is nice. Also, the BoVD is a bit ambiguous when describing what qualifies you as a sadist. According to the start of the book, anyone considered a sadist gains +1 to basically everything if they dealt damage equal to or greater than their character level the previous round, and there is no given way to attain sadist status.

For feats, pain touch is good, but there isn't that much out there for good monk feats. Going Martial Monk could grant some amazing stuff, but that's just a little bit cheesy. (Especially if you consider 21st level as a prerequisite.) Vile Natural Attack is very mediocre. If your DM is really nice, a slightly reskinned Touch of Golden Ice would be amazing.

A good substitute for monk would be the unarmed swordsage variant. It gains monk progression, wisdom to AC, and basically a whole set of spellcasting. It makes for lots of variety in play, and substantially (by ~two tiers) increases power. Also, if you go by the semi-RAW interpretation that all PrCs add full initiating, (ToB pg. 40) you could multiclass freely and keep up with your maneuvers.

A fun build to play could be a Monk X*/Ur Priest X**/Sacred Fist. Access to powerful magic, fighting abilities of a monk (however lowly they may be,) and then using both at once can be a blast. It leads to ninth level divine casting and mostly full monk progression. If sticking to a concept becomes a problem, two planar touchstones of (insert thematically appropriate domains here) would allow access to anything necessary. (ie. Evil/Undead/Baatezu, Ta'naari, etc.)

Another class to play could be the Divine Crusader from Complete Divine. Ninth level spellcasting, but only in your chosen domain. This one is on the opposite side of god-hating, if that's a plus. Also gives a few neat abilities, but its probably just best to nab the spellcasting.

If the character is into slavery, the Thayan Slaver class is cool, with a crippling strike and a few other pain based abilities. (It is arcane, however.)

When considering magic items later on, the usual monk stuff is nice, and a custom item of continuous Sadism, though expensive, is very appropriate. Also, get a wizard to permanency a Greater Magic Fang on you several times, though expensive it pays off in the long run. If you ever need money, just get a permanent symbol of pain, chain a creature down and make lots of Liquid Pain.

*Monk pretty much ends at sixth, though you could leave as early as 5th. (Or earlier, depending on what sort of early access shenanigans your DM allows.)

**Ur-Priest 1 is good for nabbing spellcasting to progress, and 2 gives your Turn/Rebuke undead, which can be used to fuel divine Metamagic. I personally like going all the way to 10 for the Steal Spell Like-Ability capstone, but that's just me.