100 Ways To Show Your Villain is Complex/Tragic

Here are one hundred different ways you can show that your main villain is a little deeper and more complex than the players might have originally thought.

1Mentioning a certain name in their presence will cause them to become visibly sullen and withdrawn, as soon as their alone, they burst into tears (Bonus points if they only really show one or no emotion throughout the campaign)
2They're actually a really good boss, and their minions have no real complaints about working for them.
3They only really target one person, and when the party finds out who and why, a trusted ally is revealed as the person who ruined the BBEG's life.
4They have a deeply held sense of honor, never attacking the party when they are clearly outmatched even to the detriment of their own plans.
5They never associate with beings known for being evil by nature.
6They think they are fighting an even worse foe, and they believe the party are agents of this foe.
7They are actually the dark side of this great, fabled hero who was so great and virtuous that tales about him are still told to this day. It could be revealed that in order to become so good and virtuous they viscerally expelled all evil from them in a painful magical manner, and that evil eventually gained consciousness. Perhaps the only way to defeat the BBEG is to kill this hero, or have the hero accept that part of themselves.
8They were a human fighter long ago, and they were cast out from every group they tried to join for being so one note and useless. His frustration turned into a burning hatred of diverse groups, who on one hand preach diversity while cursing those who are diverse simply by being different.
9His kingdom, despite all of the evil iconography and dark lifestyle choices, is prosperous, and his people love him. He came to power by overthrowing an even more tyrannical figure, and his conquests are in an attempt to make his people comfortable.
10The BBEG has gained an affection for one of the PC's or NPC's. Perhaps they remind them of a long lost friend? Perhaps the BBEG admires the traits they hold? Or maybe love has struck them at an awkward time? Whichever the case is, the BBEG often flirts with, or compliments the other character, and maybe even gives them gifts! They may even become heartbroken if the PC/NPC doesn't reciprocate these feelings and talks down to them for doing so.
11The BBEG used to be a different sort of person before some important event in their lives forced them to reinvent themselves (for example, going from a barbarian warlord to a Prof. Moriarty-esque criminal mastermind.)
12The BBEG shows warm feelings toward the PCs, praising various of their virtues and generally preferring to let them survive.
13The BBEG plays a musical instrument. They're really quite good.
14The BBEG creates memorials to those they kill, considering them tragic sacrifices to a greater good.
15The BBEG runs a hospice for terminally ill orphans, and everything they do is to raise funds and get food and pain medication for the kids. It’s just that their methods to acquire those things are a little questionable.
16The BBEG wanted to become an adventurer when they were young, but when they tried to join a party they were cruelly rejected. The PCs just happen to vaguely remind the BBEG of that other, long gone, party.
17BBEG kills one of their own underlings for a crime which they see as worse than whatever villainous stuff they do
18BBEG is a future version of an NPC or PC who went a little too far pursuing the power to defend their friend/country/interests. Now they're corrupted and too far gone, but the question of redemption is always on the table.
19BBEG is innocent enough and/or insulated from the outside world enough to be manipulated into decisions which have horrific, but invisible, consequences
20BBEG had a mean streak when they were young, then went off the grid, had a family, and left the life for a time. Family died [choose your own tragic story] and he's getting old now, so he decides to reignite the fires of anarchy and finish his grand plans.
21They have to stop mid-evil monologue to get a child a glass of water. They ask the party to ignore that, then lose their place and have to start over from the beginning.
22The Prince/Princess the BBEG kidnapped totally sides with them. It's not mind control, they just think their kidnapper made some pretty darn good points. This can range anywhere from an impassioned please to them actually helping them to win.
23The BBEG says, "You're not the only adventurers in the world." And summons their own motley crew of tragic backstory weirdos to fight you. During the fight they banter, commenting on how the real villains here are whatever church is about to get 8 - 12 adventurers worth of diamonds plus tithes for the resurrections.
24After the BBEG goes down for the first time, a celestial being appears. "Arise, my champion." They declare and suddenly the BBEG gains a second wind in a flash of light. Their stats are completely restored as they're given a second chance to defeat the group. Are we the baddies?
25The BBEG lives by a very specific - if not entirely morally good - code of conduct, even when/if it causes them issues. EG: refusing to accept offers to help them, as needing help shows weakness and inferiority - if they get a cursed sword glued to their hands, and they can't get it off themselves? It's staying on there forever, short of someone else physically tying them down and un-cursing it.
26The player-characters meet someone connected emotionally to the BBEG -- parent, offspring, sibling, ex-spouse, close friend -- who can remember back before he or she had "gone astray" and furthermore who offers to help the player-characters defeat the BBEG on the condition they promise not to kill but to capture or to give him or her one last chance to try to persuade the BBEG to recant.
27The BBEG is acting under a geas, as a price for a deal with Asmodeus to save someone they love.
28The BBEG is pursuing an understandable goal in a warped way.
29The BBEGs collection of valuable and powerful trinkets and macguffins is a collection to be put in a public museum that they are hoping to open soon.
30The BBEG has delightful children, who they want to keep out of the family business, and uncorrupted by the BBEGs plan.
31The BBEG was never noticed throughout childhood and adolescence, and is doing what they can in desperation to get noticed.
32The BBEG intends to submit themselves to the people after completing their plan. They want to let the people dole out justice, if they feel it necessary, after seeing the plan come to light.
33An even bigger existential threat is coming, and BBEG knows that everyone must be united, or fall divided. No leaders have been willing to listen, and so the BBEG is left with no choice other than force.
34The BBEG is being mind controlled by a literal evil god e.g. Cyric, who is simply bored and just inflicting malice on the plane of existence for something to pass the time.
35They are brain damaged (think a failed magical experiment/an experimental surgery/one too many blows to the head) and have a hard time understanding emotions.
36They are trying to find a cure for their comatose partner. Revealed by them to refusing to leave their lair and specifically guarding a specific door to their partner in the "boss room". Minions are sent to retrieve medical stuff, fabled potions and cures etc.. and abduct healers and scholars.
37They refuse to stoop to the parties violent ways and will always seek to trap or delay the party rather than confront them personally or with minions. Revealed when they risk themselves to release the party from a trap gone wrong, concerned it may become deadly.
38Many of the goods thought to be stolen by them end up in the hands of local orphans.
39They visibly and audibly retch at the sight of blood and refuse to carry a weapon or eat meat.
40They personally see to the wounds of their minions and will attempt to rescue their minions if the chance arises.
41A journal where they lament turning to a life of crime/evil, rather than confessing their love and retiring to the countryside. Sprinkle in a description of their ideal dream, what they would name their dog, how many children they wanted, the color of their house etc..
42The party finds their family. The family knows nothing of their evil deeds and believes the big bad to be a hardworking person and/or fantastic parent, etc..
43Many of the locals revere them, some believing them to be a heroic legend or benevolent spirit. Investigation reveals the big bad grew up there and acted as a vigilante in their youth.
44The big bad's origin story is disturbingly similar to that of the most righteous players'.
45They are renowned for their philanthropy, opening numerous poor houses and personally feeding the hungry in some giving holidays.
46They enjoy parties and are well connected with the upper class. There's no sinister plot, they just like to party.
47Their dad was a big-time villain, who built his empire with his bare hands. All the other villains think this new kid is just mooching off their dad's success. The kid doesn't want to run the family business, but the Oracle said so.
48They buy alot of slaves, though the players rarely go up against them. The big bad buys them to set them free, only some stay by choice to work for them and are paid and treated fairly. The big bad themselves grew up a slave, before murdering their master and beginning their life of crime.
49An Oracle ordained that this quest/mission was their destiny since they were young, and they feel trapped on this path.
50They own a large plot of land, said to contain all manner of vicious monsters for the big bad’s army. Strangely the party never fights any and no one has actually seen them. In truth it's a private nature reserve where the big bad collects endangered and injured animals and plants to protect them.
51The big bad surrenders, begging the players to spare their pet.
52They visit an elderly priest on the first day of each month with no exceptions. On investigation the player might notice some of the big bads minions shadowing the priest whenever he goes out shopping or to visit the local healer etc.. The players will spot the priest being pickpocketed, followed by the minions subtly killing the pickpocket and returning the priest politely stating "Be careful, old man, you dropped your purse". The old priest is unaware of their secret bodyguards and is just a nice old geezer that used to run the big bad’s orphanage.
53They live with an elderly parent/ relative who knows all about and disproves of their life choices, but tries to be supportive. If discovered they will aid the player in stopping the big bad on the condition the players don't hurt them.
54They leave notes pleading with the players to see their point of view.
55The BBEG has published many popular children's books and a philosophical discussion on the morality of necromancy between themselves, a famous general and the local undertaker. The big bad concluded necromancy is fine if the corpse is soulless/mindless or volunteered, the general believes all necromancy would be fantastic and save many lives, the undertaker is out of his depth and mostly talks about how it would save him digging so many graves.
56They are unhappily in love and just want to prove to their true love that they are relationship material. But despite all their efforts it seems to just not be enough.
57Their lieutenants are much more ruthless than them and nearly amoral, but are kept in check by undying loyalty, and would never betray their friend's vision of a better world.
58They react childishly to trivial defeats, such as board games.
59Despite their outward confidence, they have a secret self-deprecating sense of humor they resort to under stress.
60Evil isn't something they like, but it's the only thing they have left in their life, and pursue it as a way of avoiding existential dread.
61Due to differences in culture and/or psychology, they genuinely don't get why everyone seems so hung up on the whole "mass murder" thing.
62Their "evil goals" are a grief-tainted version of the ideals a lost loved one of theirs had.
63They take oaths seriously. Very seriously. Uncomfortably seriously. If they must break one, they will do so by only following it to the letter.
64The BBEG and their supporters genuinely believe they are doing the right thing, and that they are the heroes of the story fighting against forces that don't understand why they are necessary.
65The BBEG only employs those who have no jobs or have been rejected by society.
66They have the same goals as the party but take "the end justifies the means" to an uncomfortable extreme.
67They are legitimately beloved by people for their good deeds in the past, unaffected by or unknowing of their current status.
68They have a sacred place. This doesn't need to be religious but it is a place they will not "work" in. If this is their house then they may invite the party in as guests... seeing as they already showed themselves in and then cook a non-poisoned dinner.
69They are trying to stop a coming calamity that will never come to pass. Their soul now but an echo of a brave hero that once saved the world, unable to see past that end goal.
70The party finds them having a bad day so they ask politely if they can just do this some other time. Maybe they'll even just agree to stop their plans for the day or something.
71They lost someone and now the world has nothing left for them. Perhaps they secretly want to die but instead channel their despair into the actions that make them the bbeg.
72They are desperately lonely, but opportunities to strike up reciprocal and mutually beneficial friendships or relationships with other sentient beings do not occur to them. When suggested, they respond with incredulity.
73They are not actually aware of most of the evil their subordinates are causing. All they do is provide resources, provide support, and set quotas; the only thing they've ever done is remove employees who don't make enough money. As long as the cash keeps coming in, they're a 'hands-off' employer.
74They wield a spear which mythically can only be carried by the pure of heart.
75Even though they designed whatever mechanisms of evil exist, things have spiraled out of control. In truth, they want this all to end—but they are ensnared by their own designs, and don't think that there's anything they can do to save the situation.
76They possess an artifact or tool which would allow them to have all that they desire, but at horrible cost to the world. Most notable about this is that they have not used it.
77They were once just a curious researcher who was corrupted by the very thing they wanted to understand.
78Our heroes prove to benefit greatly if the Villain succeeds in their otherwise horrific plans, motives or methods.
79Their reasoning is archaic, anywhere from a generation gap to eons-old customs.
80They are making sport with other major villains in some kind of game that's been twisted by time, or malice. Our heroes may have been inadvertently caught up in it.
81The Villain is a close family member to one of our heroes, and they have good reason to care for each other.
82They deeply believe they are the chosen hero of an ancient prophecy, which puts them on the path to destroying the world and allowing a Perfect Utopia to rise from the ashes.
83They just really love swordfights, and have gone so deeply into their obsession that they won't stop until every hero, paragon of goodness or not, dies at their hand. They just happened to be on a hot streak of killing true Heroes.
84They're a ghost of their former self, so far gone from reason that all they can even comprehend are their terrible machinations. They are insane and clearly angry or depressed, yet they know not why.
85They're romantically involved with one of the party members. Perhaps a spouse or a lover, crossing paths only occasionally but a heated romance and inevitable argument casts your paths away again.
86They're a dumb, scared animal. Maybe even a young one divided from their parents. Probably lost.
87They go to extreme lengths to hoard a precious resource, only later to reveal the resource has potential to wreak terrible havoc on the people.
88Same as above, but they reveal instead a belief that the precious resource can somehow be used to destroy, enslave, corrupt or impoverish them personally.
89They are a horribly spoiled child, who rules by birthright and the unfortunate recent death of their former Ruler. Their top subordinate or religious figure demands the Ruler be honored in all demands, requests, questions and written orders. Their lands are in chaos.
90An extremely gullible drunk is just being manipulated by a possessed helmet.
91Their evil motives are purely driven by something nonsensical or petty, like what day certain foods can be sold, not adhering to certain dress codes, or a simple hatred for those damned evil dogs in their lands.
92They're genuinely trying to mentor one or all of the heroes. They give them really good advice and prove their support of them. Maybe they distrust one or more of the party, thinking of them as a bad influence.
93They're just a bit of a kook, going to extreme, somewhat absurd lengths to achieve a similarly absurd goal.
94They are an undead/outsider/of a race who is inherently evil, they rule a kingdom, and they can be identified to have an evil aura. Though evil to his core, he has realized that by making the people he rules happy, it serves his self interest in that he has power without having to deal with scheming evil underlings who want to claim his throne for themselves. The kingdom has the highest quality of life anywhere in its area of the world, but how do you let someone or something so evil rule over normal people?
95The BBEG is actually a God trying to fulfill their role in the realm, which has been halted by the actions of another God.
96Whenever they kill, they ask if their victim has any last requests. They won't do absolutely anything for the victim—after all, they've decided that they need to die to further their goals—but the BBEG takes the requests very seriously and will fulfill them within all reason.
97When they're finally defeated, mortally wounded, the villain has a last request to the heroes. They'd like a song to go out on.
98The BBEG believes that if their plan (which would kill tens of thousands at bare minimum) is not enacted, the world will certainly be destroyed.
99The villain commits their evil in the name of discovering arcane secrets which could save lives or revolutionize the world—they plan to share these secrets without any qualifications, and have proven their willingness to do so in the past even when it costs them tactical advantage.
100The villain prays for the forgiveness of their god before each act of violence they commit.