Part 1: https://www.fimfiction.net/group/41/crossovers/thread/497225/what-dd-classes-would-mlp-characters-be-pt-1
Part 2: https://www.fimfiction.net/group/41/crossovers/thread/497857/what-classes-would-mlp-characters-be-in-dd-pt-2.
Part 3: https://www.fimfiction.net/group/41/crossovers/thread/498055/what-dd-classes-would-mlp-characters-be-pt-3

Here we go ladies and gentleman! The final entry in the series where I talk about what MLP characters would be like in a D&D setting and this time we’re building a party for an evil campaign. The plot that assembles this team together is pretty simple. It’s more or less the season nine arc with Grogar gathering all the other villains when they’re at their lowest point… except he’s for real this time. He has them go a quest to get several important items for him in exchange for having their deepest desires granted.

Fourth Party - The Evil Campaign

Tempest Shadow: Monk (Kensei)/Fighter (Battlemaster)
I think these one of the most fitting yet non-obvious classes I’ve selected for an MLP character. With the Kensei’s proficiency in both weaponry and martial arts and the Battlemaster’s advanced battlefield tactics/big-brain energy, it combines to create a character with the same feel of the show-stealing antagonist we got in the MLP: Movie.
She would act as the party’s de facto battlefield commander and tactician as well as the one who handles one-on-one interrogations. Though she’s obviously going to have her hooves full trying to get all these egomaniacs to listen to her.

Cozy Glow: Bard (College of Eloquence)/Rogue (Mastermind)
This is another one I’m very pleased with. Combining the Mastermind’s proficiency at sizing up who they’re talking to and Eloquence Bard’s way with words and mastery of persuasion helps create a build for the ultimate master manipulator.
I imagine her being the best team player in this group. Cozy Glow is exactly the type who’s willing to appeal to her teammates’ egos to inspire the best out of them. Whereas Tempest is the combat commander, Cozy takes the lead in social situations as the group’s face; she also plays the good cop to Tempest’s bad cop. Her biggest moments to shine are when she’s able to convince crowds of unsuspecting townsfolk into helping them do the team’s dirty work.
Also, not that it matters, but if I were to give her an instrument it’d probably be a harp, though College of Eloquence doesn’t seem to require any instruments let alone music.

Tirek: Paladin (Oath of Conquest)/Warlock (Undead - Pact of the Blade)
This choice of multiclass is probably a little more random compared to the rest. All I knew is that I wanted Tirek to be both a caster and a close-quarters fighter just like we saw in the season four finale. I also wanted to find at least one more character who I can make into a warlock and another character to make a paladin as well. And after a lot of thought, I realized Tirek was my best chance to get both of those classes.
I put Paladin first because that’s the order in which he becomes them, but I prefer to think of warlock as the primary class here.
I like how I can reimagine several of Tirek’s abilities as Warlock spells. Those beams he shoots from the space between his horns can be him spamming eldritch blast and his magic absorption can be something similar to vampiric touch. He made the pact with his patron after escaping Tartarus and discovering their lamp. As for why I made him strike a pact with a genie specifically, it’s so that the genie can grant him several wishes in exchange for stealing all the magic in Equestria and using it to free the genie from their imprisonment. His wishes include world domination and gaining revenge on his brother Scorpan for betraying the Oath of Conquest that they both swore to and ratting him out to the ponies.
An alternative idea for a patron that he can strike a pact with could Grogar himself. And once again

Sombra: Sorcerer (Shadow Magic)
Making him a shadow sorcerer was an obvious choice, though I also was originally going to make him the Conquest Paladin. Then I realized that between the two, Tirek does more close quarters fighting than Sombra. As a shadow sorcerer, he’s most useful to the team in nighttime settings and dungeon crawls. He’s also very proficient in enchantment magic, which will come in handy during situations where Cozy Glow’s persuasive abilities don’t prove effective enough.

Chrysalis: Wizard (School of Illusion)
Illusion magic is thematically perfect for Chrysalis, though I must admit her natural shape shifting ability would make disguise self entirely pointless. On top of illusions, she also has some enchantment as well, though that’s still more Sombra’s territory. A part of me wonders if her and Sombra would have that classic Wizard-Sorcerer rivalry.
Chrysalis and Cozy would be the biggest sources of the team’s wiliest plans. I would even go so far as to deem Chrysalis the party’s strategist, her plans usually specializing in sabotage and subterfuge.

Well, that’s the end of that. I had a lot of fun making these and I hope you got as much enjoyment out of reading them too.

7707783
For Tempest, I'd go with this https://www.dndbeyond.com/subclasses/44487-way-of-the-lightning-storm and not bother with the fighter. Anyone can have advanced tactical knowledge, and monks are expected to anyway (the monk's play style is meant to be hit and run gorilla warfare, after all).

With Tirek, I would have gone with a reflavored oathbreaker. The abilities of the oathbreaker fit him more. You could call it the Oath of Subjugation or something.

Now, for Chrysalis, this might surprise you, but I'd go with Great Old One warlock. Chrysalis is all about mind fucking her enemies, and no one does that better the GOO warlock. Spells like dissonant whispers, and dominate person, as well as features like awakened mind and create thrall just screams Chrysalis. Also, she never really uses illusions, only her racial feature to shapechange (there IS an official changeling race, after all, and this is a racial feature), and her own charms. Plus, the GOO is based off Lovecraftian monsters and many of those feed off emotions.

P.S. You forgot about two villains that easily rank up there with these, two that, in an alternate timeline, also conquered Equestria; Flim and Flam!

7707803

I’d find this subclass as an acceptable alternative for Tempest. But I still stand by my build for her. I think going with Kensei gives a different flavor of monk that we haven’t seen in my previous parties. We had RD who used her ki to be a part caster, Sandbar who focused entirely on the unarmed martial arts, and now Tempest who’s a weapons master. Plus, can you imagine how much more deadly she’d be in the movie if she were allowed to use weapons too? As for the Battlemaster as a multiclass, if she’s going to be the team’s field commander, she might as well be the subclass who’s moveset is specifically designed for that. I just think she’s the one who feels the most like a Battlemaster out of the rest of the cast.

You’re idea for Tirek as a reflavored oath breaker is interesting, but for some reason I just get major warlock vibes from him if that makes any sense. I don’t know if you’re objecting to the idea of him as a warlock at all, so clear that up for me if you can. But, I’m also not sure how the oathbreaker’s abilities are a better fit for Tirek, he doesn’t seem to be involved in necromancy.

Regarding Chrysalis, you’re sort of right. We obviously from A Canterlot Wedding that she does indeed know mind control spells, that’s why I specified that she also has some enchantment magic in her repertoire. However, most of her plots have been reliant on trickery rather than straight up “mind fucking”. So, that’s why I chose the illusion wizard as a natural expansion on what she does in the show. Plus if you can say that her shapeshifting abilities doesn’t mean she’s a good illusion wizard, then I can easily say that her natural ability to feed off emotions doesn’t necessarily make her a Goolock. I’d rather leave the enchanting to Sombra anyway, as we see him do far more mind control in episode one of season nine than we see Chrysalis do in the entire show.

Glad you seem to agree with me on build for Cozy Glow though. I was very proud of that one.

7709701
Why would Tirek be an Oathbreaker? Hellish Rebuke, Inflict Wounds, Bestow Curse, Blight, Dominate Person, Dreadful Aspect, Aura of Hate, and Dread Lord. Need I clarify further?