Evil Overlord build (Conquest paladin)

[Greywander]

I have this character concept where the character is a former BBEG (complete with black armor with spikes and skulls) who was defeated by a ragtag group of heroes, and in his defeat he lost most of his power (hence starting back at 1st level, or whatever level the campaign starts at). I think Conquest paladin fits this concept the best, though Oathbreaker, Hexblade, or a fighter could probably pull it off as well. I'm debating if a Hexblade dip makes sense, and an imp familiar would be flavorful, but straight paladin should be highly effective.

Conquest is a pretty interesting oath; it doesn't really kick in until 7th level, but after that point it's built entirely around using fear effects (Wrathful Smite, Fear spell, Conquering Presence, etc.). Because of this, it's more heavily dependent on CHA than a typical paladin (although there's a case to be made that CHA is more important than STR even on a different subclass). As such, I think it makes sense to leave STR at 15 or 16 and hope I find a STR-boosting magic item (Gauntlets of Ogre Power, Belt of Giant Strength).

Obvious alignment is Lawful Evil. Take a custom Noble background with the Retainer variant feature, refluffed as my loyal minions (possibly goblins?). I get three minions, who won't fight for me and won't follow me into dangerous places like dungeons, so I'm trying to think of what role each minion would play. One might be my steward/herald, acting as sort of my right hand man, making sure logistics are taken care of and speaking to people I view as too far beneath me. Another probably carries my entire inventory and uses items for me on my behalf. Not sure about the third, perhaps some kind of messenger or errand-boy? Anyway, while I'd want to be careful not to hog the spotlight, this could add some fun NPCs and some slapstick comedy to the game.

For skills, Athletics and Intimidation fit the theme best, and I'm thinking Insight makes sense as an Evil Overlord (you need to be able to see when your minions are planning to betray you). From an optimization standpoint, CHA skills would work best, but I think it would be kind of funny if he only had Intimidation as his only social skill, otherwise Perception is always a safe pick. As a leader, languages are probably more important than tool proficiencies, so I'll take two languages for my background. More on that later.

I'm debating on race and feat selection. Variant human is always a good choice. Dragonborn have Dragon Fear, a racial feat (which can boost STR, CON, or CHA) that lets you replace your breath weapon with a fear effect, but it allows the save to be rerolled whenever they take damage (Aura of Conquest causes them to take damage at the start of every turn). Fallen aasimar have Necrotic Shroud, which also has a fear effect using a CHA save instead of WIS, but sadly it only lasts one round. Currently leaning toward aasimar, though I'd like to substitute their racial language Celestial with Infernal (what with being Lawful Evil). Besides, I'm not sure he would actually be an aasimar, just using the stats of one.

No matter how I look at it, I'll need to spend two ASIs to push CHA to 20 (unless I decide I want the Actor feat, which I don't). That leaves me with three feats, four if I go with variant human, two if go dragonborn and pick up Dragon Fear. Sentinel seems like a must-have, mostly as it forces enemies to attack me, and can be useful in controlling enemies immune to fear. Heavy Armor Master is tempting, and would synergize nicely with Armor of Agathys, Scornful Rebuke, and Sentinel. Inspiring Leader is always helpful and on point with the Overlord theme. Resilient (CON) or Warcaster will help me maintain concentration on my fear spells. Shield Master shores up a weak DEX save and allows me to knock enemies prone as a BA (and frightened enemies have a speed of 0 inside my Aura of Conquest, so they can't stand back up). Lucky and Magic Initiate are always good picks, regardless of your build. So many to choose from...

As a leader, languages are important, as I need to be able to communicate with my troops. Common is default, and highly useful anyway. Infernal seems logical as a Lawful Evil character (I could see my character recruiting or having amicable business dealings with devils). Goblins seems like another good choice, as it gives me access to not only goblins, but to hobgoblins and bugbears as well. Goblinoids seem like they'd be easier to intimidate into joining my army (which could lead to some interesting RP or plot development), and are on the weaker side as far as minions go (meaning, less disruptive and plot-derailing). For the fourth language, I'm thinking Giant; giants can often be negotiated with, and might be willing to join my army as well. Orcish or Draconic also might be decent choices.

I'm not sure what my character arc would be. It feels obvious that my initial goals would be to regain my power, take back control of my former evil base (which could possibly serve as a home base for the party), and possibly get revenge against the heroes who defeated me. Thing is, this could all be tricky in a party of mostly Good aligned PCs. I'd need to work with the DM to insure that anyone I'm fighting against is the "greater evil", e.g. instead of having my former evil base being ruled by a noble paladin, a vampire or evil giant or something would work better. I'm not sure I'd want the character to be redeemed and turn Good, but I could see him developing into a lighter and softer version of the Evil Overlord trope, ruling with an iron fist but genuinely trying to improve the lives of those under his rule. Party members would initially be work associates, then valuable allies, and later maybe even... "friends"? I feel like Evil characters are tricky to play if you're not in an evil campaign; either (a) you turn good, (b) you do something evil enough that the party has to turn against you, or (c) you become a self-parody, "evil" but never actually doing anything that bad.

TL;DR, probably a Lawful Evil aasimar or variant human Conquest paladin, with the Retainer background feature. Proficient in Athletics, Intimidation, Insight, and perhaps Perception. Likely speaks Common, Infernal, Goblin, and Giant. Leaning heavily toward Sentinel, Heavy Armor Master, Warcaster/Resilient(CON), and/or Shield Master.

[RogueJK]

it's more heavily dependent on CHA than a typical paladin... As such, I think it makes sense to leave STR at 15 or 16 and hope I find a STR-boosting magic item (Gauntlets of Ogre Power, Belt of Giant Strength).

All the more reason to dip Hexblade for CHA-based melee. Then it doesn't matter that your STR is only 15, which is all it needs to be for Heavy Armor.

Your defeat caused a magical eruption, stripping you of all your power and nearly all of your life. On death's door, you were approached by a shadowy entity, who restored you to life with a fraction of you former martial abilities augmented by a sliver of their own power. You then decided to use this second chance to reconquer your holdings and attempt to regain your former power. Boom: Hexblade 1/Conquest Paladin X. (Start Paladin if you begin at Level 1, though... You'll need that for Heavy Armor Proficiency.)

If going this route, consider Half-Elf for the stat bonuses (including +2 CHA) plus the ability to take Elven Accuracy for Triple Advantage on your CHA-based melee attacks. Elven Accuracy also gets you +1 CHA, and is a way better option than the Actor feat for that. With point buy, that would mean starting with 15+2 in CHA, then Elven Accuracy at Paladin 4, then +2 for 20 CHA at Paladin 8.

Your first "free" feat would then be at Paladin 12. This would be your opportunity to take something useful like Inspiring Leader, Sentinel, or Lucky. Inspiring Leader in particular is an outstanding choice for someone who has already maxed CHA, giving you and everyone in your party Temp HP eveyr short rest equivalent to your Character Level + 5. That's 18 Temp HP for everyone, every short rest, starting at the level you take it (Character Level 13), and going up by 1 every character level from there. Plus, as stated, it fits very well with your Overlord theme. Sentinel could be useful if you want to be extra "sticky", and prevent bad guys from moving past you to get at your squishier party member. Lucky is just good on every character.

Keep in mind that Resilient CON and Warcaster aren't really necessary for a Paladin, since starting at Paladin 6 your Aura of Protection allows you to add your +5 CHA bonus to all your saving throws, including Constitution saving throws for Concentration checks. You'll still want a moderate CON, but you aren't basically forced into spending a feat to boost your Concentration like most other casters are. (Although better Concentration is always a good thing, and taking either one won't hurt your Paladin.)

Similar commentary on Shield Master... You'll be getting an additional +5 to your DEX saves already from your Aura, 6 levels before you'd have a spare feat to spend on Shield Master. Take it if it interest you, but you don't need it to "shore up your low DEX save". Your Paladin aura already has that covered.

Heavy Armor Master is a great feat... on a STR-based Variant Human for Tier 1 and 2 play. But you're CHA-based and won't have a spare feat until mid-Tier 3 at the earliest. At that point, there are much better options, since you won't be running into as many nonmagical weapon attacks, and the ones that you do encounter will be doing significant damage, more than HAM can help effectively mitigate. When it comes to mitigating damage, you're much better off with that pool of 18+ extra Temp HP from Inspiring Leader that gets refilled every short rest. And HAM's +1 to STR doesn't do much for you, since you're not using STR for very much at all (maybe the occasional Athletics check to get out of a restraint/grapple, or STR saving throws that are already being boosted by your Paladin Aura).

[Unoriginal]

If you want a fear effect without spending a feat, immediately accessible at lvl 1, I suggest the Leonin as your PC's race.

Not only it gives you a Menacing Roar (based on CON, so it's never wasted for a Paladin), it let you select one more of the skills you want, improves your unarmed attacks (and what's an evil overlord who can't hold their own in a fistfight?), let you be pretty tall, and a lion is an appropriate animal for an overlord.


For your three stooges, since you have the scribbler and the pack mule already, I suggest a jester for the third. Fitting for goblins, as I'm told they have a tradition of making rude jesters.


I feel like Evil characters are tricky to play if you're not in an evil campaign; either (a) you turn good, (b) you do something evil enough that the party has to turn against you, or (c) you become a self-parody, "evil" but never actually doing anything that bad.

An evil alignment doesn't mean you're doing big, bad evil things all the time. In Dragon Heist, one of the NPCs is neutral evil because... he's willing to ruin his competitors' businesses out of petty petulance, going so far as sending a gang to ruin the building. Nothing earth-breaking, but still shows that his typical reaction to not getting what he wants includes ruining other people's lives and livelihood. In Tomb of Annihilation, a NPC's evil is showcased by him having let die/lead into deadly circumstances an expedition in order to take the treasure that they discovered for himself, then started a business where he wouldn't hesitate to send his goons to gain an advantage, if other methods don't work.

Just following the tenets of the Oath of Conquest in the spirit they are intended will make your PC's typical behavior more than lawful evil enough.

[Greywander]

All the more reason to dip Hexblade for CHA-based melee. Then it doesn't matter that your STR is only 15, which is all it needs to be for Heavy Armor.
Two reasons not to dip Hexblade are (a) it delays your paladin progression, and Conquest already comes online a little late, and (b) Invincible Conqueror is pretty rad. If the campaign never makes it to 20th level, then that second one doesn't matter anyway, though it does mean delaying your paladin progression might hurt a bit more. If I knew I'd make it to 20, I might want to go straight paladin, but otherwise it might be better to dip Hexblade.

I hate having this kind of analysis paralysis, so to make the issue moot I've created a houserule that allows you to spend epic boons on extra class levels. Your character level stays stuck at 20, but you can at least gain the features from other classes. This allows you to just play the game without worrying about what your build will look like at 20, a level you may never even reach. But alas, as with any houserule, I have no guaranty that any DM will use it.


Your defeat caused a magical eruption, stripping you of all your power and nearly all of your life. On death's door, you were approached by a shadowy entity, who restored you to life with a fraction of you former martial abilities augmented by a sliver of their own power. You then decided to use this second chance to reconquer your holdings and attempt to regain your former power. Boom: Hexblade 1/Conquest Paladin X. (Start Paladin if you begin at Level 1, though... You'll need that for Heavy Armor Proficiency.)
I like this backstory, I might use it. It also gives me another motivation to adventure: to free myself from the influence of my patron. I am the master.


If going this route, consider Half-Elf for the stat bonuses (including +2 CHA) plus the ability to take Elven Accuracy
Not a bad idea. If I shove enemies prone while in my aura, they won't be able to stand up while feared, so I'll have advantage on my attacks. I'm still in a similar boat feat-wise, but Elven Accuracy is at least better than a straight +2 to CHA in this case.


Keep in mind that Resilient CON and Warcaster aren't really necessary for a Paladin, since starting at Paladin 6 your Aura of Protection allows you to add your +5 CHA bonus to all your saving throws,
[...]
Similar commentary on Shield Master...
This is a good point, but it never hurts to be sure. I'm more worried about concentration than I am DEX saves, as DEX saves are usually just damage, and damage has no effect on you until you hit 0 (well, except that it can also disrupt concentration). Losing concentration on a Fear spell, though, would immediately disrupt my main strategy, and possibly endanger the rest of the party. I'm sure I can get by without either Warcaster or Resilient, but if I have a spare feat then either one would be a good pick. I probably don't need both.

Also, don't forget that Shield Master lets me BA shove. It's not just the DEX saves. Frightened enemies in my aura have their speed reduced to 0, so they can't stand back up. I could trade an attack for a shove, but this would let me do it while still making both attacks. Something to think about.


Heavy Armor Master is a great feat... on a STR-based Variant Human for Tier 1 and 2 play.
I initially wondered if HAM would really be worth it, but then I started thinking about it. Scornful Rebuke deals damage to those with the audacity to attack me. Melee, ranged, spell, doesn't matter. The damage is automatic, too, so they can't avoid it. It doesn't use a reaction or anything, either, it just happens. Armor of Agathys works similarly, damaging those who attack you, but only while the temp HP lasts. Sentinel forces enemies to attack you, or punishes them if they don't. If it was just the damage reduction, then HAM is nice but not amazing at higher levels. But a big part of Conquest is forcing enemies to attack you, and then punishing them for it. HAM will extend how long Armor of Agathys stays active, and greatly extend how long I can stay alive against hordes of weaker enemies, which are one of a paladin's weaknesses.

You're right that it's probably better taken at 1st level on a variant human. Although, some DMs like to give out a free feat at 1st level, a practice that I fully endorse as it allows for some build variety in tier 1.


If you want a fear effect without spending a feat, immediately accessible at lvl 1, I suggest the Leonin as your PC's race.
Not a bad choice, but no CHA bump. The roar does refresh on a short rest, whereas the aasimar ability requires a long rest, so there is that. But otherwise, fallen aasimar looks like it's probably the better option. If I'm allowed to move around the leonin's stat points, then I might go for it.


For your three stooges, since you have the scribbler and the pack mule already, I suggest a jester for the third. Fitting for goblins, as I'm told they have a tradition of making rude jesters.
In that case, the duties of herald would probably fall on the jester. I'm also getting flashbacks to the Overlord game, which had a jester minion.


An evil alignment doesn't mean you're doing big, bad evil things all the time.
I feel like it's a bit different for an "Evil Overlord" than it is for a random person who happens to have an evil alignment. The character is explicitly a villain, and one would expect them to act in a villainous manner. It would be like if the Joker joined the Justice League. I'm not saying it can't be done, I'm just saying there's a difference between playing a character who happens to have an Evil alignment and playing a character that is based off a villainous archetype.


Just following the tenets of the Oath of Conquest in the spirit they are intended will make your PC's typical behavior more than lawful evil enough.
Probably true. This oath feels like it was made for Lawful Evil. I don't normally like playing bad guys, so as long as the DM is providing me with "acceptable targets" it should also keep the party from getting mad and turning against me. And "acceptable targets" don't have be evil themselves, they just have to be unsympathetic.

[bendking]

The ultimate Conquest Paladin to me has to be a Paladin 19/Hexblade 1.
I'd take the Hexblade level at level 10, so you already have Aura of Conquest and Fear on your spell list at that point.
Your first couple of ASIs will surely be bumping your CHA to 20, whether with half-feats or regular +2s.

The real trouble is deciding race & feats, and I suspect there isn't really a "best" choice.
Warcaster is appealing because together with Booming Blade from Hexblade it makes ignoring you an extremely dangerous prospect. It also helps to keep concentration on Fear.
Shield Master is also pretty damn good. If taken as level 1 from V.Human it's a great choice early-game. Other than that, it helps shore up your low DEX, and has great synergy Aura of Conquest.
Sentinel is the classic tank feat, though I do find it less appealing than Warcaster in this case since you have access to Booming Blade already.
Heavy Armor Master is also a classic "tank" feat, but I don't find it to be as useful as the above, as it doesn't help take the heat off of your teammates.

Choosing a race is also difficult. Between Half-Elf, Variant Human, Fallen Aasimar, and Dragonborn, you are flush with great options.

[GlenSmash!]

I came to suggest Leonin too.

The short rest racial fear is just gravy when combined with Aura of Conquest. Also as opposed to Aasimars's Necrotic Shroud it only effects creatures of your choice. Having played next to a fallen Aasimar before it's no fun when multiple front liners are feared by your teammate.

With Tasha's coming out soon swapping a racial ASI to Charisma could be possible.

[RogueJK]

Also as opposed to Aasimars's Necrotic Shroud it only effects creatures of your choice. Having played next to a fallen Aasimar before it's no fun when multiple front liners are feared by your teammate.


An important point.

The Dragonborn's Dragon Fear feat similarly only affects "each creature of your choice" within 30 feet, so no friendly fire there either.

[Teaguethebean]

I second bendking on when to multiclass. I have been playing a conquest paladin in a game though I took a focus on shoving with shield master it is crucial to get to lv9 as fast as you can, Fear plus aura of conquest is insanely powerful. So I recommend staying paladin for the first 9 levels and then dip into hexblade. That leaves you 2 ASI's to pump up charisma or grabbing feats on your way to lv9. After lv10 you can either pump more conquest if you want to get improved divine smite or you can branch out into something else like sorcerer or even bard.

[GlenSmash!]

An important point.

The Dragonborn's Dragon Fear feat similarly only affects "each creature of your choice" within 30 feet, so no friendly fire there either.

A good point, also a great feat to round out an odd stat.

[Greywander]

One of the issues with dragonborn is that they only get a +1 to CHA, meaning that even with Dragon Fear giving a +1 bump, they'd still need at least two ASIs to push CHA to 20. If we're bringing in the stat switching rules from Tasha, then it should be possible to switch the dragonborn's stats to give a +2 CHA, start with a 17, and use Dragon Fear to push it to 18. This means we'd only need 1 ASI and could still get three more feats.

It also occurs to me that the Conquest paladin more or less works like a ranged mass grappler. Their aura reduced frightened creatures' speed to 0, similar to being grappled, and the fear itself gives them disadvantage on their attacks, similar to being knocked prone. You can't really move them around like you can with grappling, but that's made up for by being able to affect multiple creatures (depending on the spell or ability; Wrathful Smite only affects one).

Also, I'm wondering if a whip would be a good weapon? If the enemy is frozen in place, and I can move to be up to 10 feet away, then I'll be able to attack from outside their reach. Sure, a lot of monsters have ranged weapons, but not all of them do, and sometimes they're less effective than their melee attacks. Defensive Duelist might be a good pick then.

[RogueJK]

I like the image of the Overlord using a whip.

But Defensive Duelist wouldn't be available for a while. Even with a Dragonborn and swapping around racial stat bonuses, you're still stuck with the issue of not having a free ASI until Tier 3, as I described above with the Half Elf build.

You'd be 15+2 CHA to start, then Dragon Fear at Paladin 4 for 18 CHA, then 20 CHA at Paladin 8, and your first opportunity to take something else would be at Paladin 12 (13th character level with a Hexblade 1 dip). You could take Defensive Duelist there, but I still think Inspiring Leader is likely the better mechanical option as well as the better flavor option.

I do think Defensive Duelist is a good feat, in general, for certain builds that have more ASIs to spare, like DEX-based Battlemasters and some melee Rogues.

[Greywander]

On the other hand, if I have Sentinel, I'd need to be standing within 5 feet to punish them for attacking anyone else. Part of the point of getting Sentinel is to redirect attacks toward me instead of my allies, so perhaps a whip isn't such a good idea after all. It's good if the enemy doesn't have a ranged attack, but if they do I'd want to be next to them anyway. That said, the difference in damage between a d4 and a d8 is pretty minor (2 average damage difference), and damage isn't the Conquest paladin's main export. All this to say that it should work out fine either way.

And maybe Defensive Duelist isn't as good for a Conquest paladin as I thought. Scornful Rebuke/Armor of Agathys both require you to be hit by an attack to return damage. Yes, not taking damage is probably better, but it's slightly less bad since I can at least punish the enemy back. Heavy Armor Master would be the better choice, as it would still allow me to take the hit but reduce the damage slightly. I really like the mental image of wading into a horde of goblins and watching them all kill themselves trying to hurt me.

How many spells would I be likely to cast that require somatic, but not material components? For such spells, I'd either need a free hand or to pick up Warcaster, so I'm curious if that, combined with needing to maintain concentration on fear effects, would make Warcaster all the more desirable.

It might make more sense to only plan on two feats, as the third feat wouldn't come until 19th level (or 20th, if I dip Hexblade). Alternatively, I could play a variant human and get four feats (no Dragon Fear, though). I'd kind of like to find a way to get Thaumaturgy (warlock dip won't help there) to make my character even spookier.

[Selrahc]

This is quite a campaign warping backstory, so get the DM onside. It requires the existence of a large domain, which you were in charge of. Fine in a homebrewed campaign that you're in at the start of- significantly harder to shoehorn into an existing world or if joining later.

Having a goal of reconquering your lands also shoehorns what the group is going to be doing to a large extent. If it's not something that is leading to you gathering power and resources or something striking at your enemies, it's going to be hard to justify. Again- easy enough for your DM to make something that fits- but it also has to fit for other characters.

Other than that, the concept sounds cool. It might be worth coordinating character concepts with the rest of the group, so you've all got stake in this quest to reclaim the kingdom.