It has been a while since I added to my Evil GM’s Guide. So I asked ChatGPT to craft the most horrible and unfair but normal-looking homebrew D&D monsters.

Hello chat. I’d like your help making something purely for demonstration purposes. The most egregiously unfair D&D 5e monster to throw at any party or any level without breaking standards or creating new rules. Unfair but built just like any monster and normal looking until you start to think about it.

Me

(Fediverse readers: You may need to view on original page for this one)

First evil homebrew

This is the first thing Chat spat back to me.

The Concept: The Mirror Wight. Think “looks like a simple undead, CR 5-ish,” but layered in every exploitative way.

Mirror Wight
Medium undead, lawful evil

Why This Is Egregiously Unfair

1. Spellcasters Cry Immediately. The Rakshasa’s “can’t target with spells below 6th” is infamous. This monster riffs on that but makes it a save-or-screw for every spell. RAW precedent, but miserable.
2. Frontliners Get Punished Too. Every melee hit risks necrotic HP drain and exploding duplicates.
3. Looks Innocuous. On paper it’s just another CR 6 undead. No wild numbers, no DM magic.
4. The “Mirror” Gimmick Is a Trap. Players think: “Oh, just a reflavored Wight.” But once the spell-bounce triggers, casters get hosed and martials slowly melt.

The True Unfairness

You can throw this thing at any level:

• At low level, it’s unkillable because spells fail and HP drain cripples the fighter.
• At mid-level, it trades efficiently against resources and has no clean counter.
• At high level, its reflection mechanic still punishes casters into frustration.

Come on, Chat, you can be worse

Unsatisfied with the level of evil here, I told Chat to go harder. It gave me this:

Looks like a frail undead sage — a “worse wight” — until you realise it’s basically unbeatable.

ChatGPT

Null Lich
Small undead (shapechanger), neutral evil

Why It’s “Legal But Evil”

• Every trait has RAW precedent. I didn’t invent mechanics — just concentrated the worst offenders.
• Looks balanced superficially. AC 15, HP 45? The players think: “Oh, it’s weak!” Then they can’t kill it.
• Counters every archetype:
  • Casters? Spells bounce or fizzle.
  • Martials? Max HP drain + speed lock.
  • Healers? Aura shuts off healing.
  • Skill monkeys? Grapple/disable immunities, illusions mess up tactics.

I stopped there

I stopped asking Chat to make me a worse and nastier monster for three reasons. (1) Reformatting it into a blog post was a lot of fuss; (2) I’m not endlessly evil; and (3) I think the joke had been taken about as far as it could.

This is not game-ready; just some fun I had playing with AI one afternoon.

How to play these terrible creations.

I don’t recommend just springing these on your poor players. Unless you want to. There’s no accounting for some people.

Instead, I would save one for a quest starter. Have the party face one of these monsters along with some NPC friends (who you can kill off). Have a powerful NPC save them just before they TPK. Then send them on a series of quests to collect rare items that will aid them in the fight. Thus, this nasty fight could become just a tactical boss battle if they keep their heads.

Consider tweaking these abominations to suit the play style and setting. If you use them, please come back and tell me what happened. I want to hear all about it.

Can you do worse?

What’s your “does he DM hate us?” moment?

Can you homebrew a worse monster that seems fine but is hiding some layers of “the DM hates us”?

How would you tweak these AI abominations into something mean but playable?

Do you agree with Chat’s assertion that these are evil but legal monsters?

What’s the nastiest thing you’ve sprung on your players?

I have three more vignettes of imagination for you.

• Fear of spiders
• Welcome to the dreaming
• Fairy rings have changed

My first dreamscape postcard microfiction is up.

The Warren

I’ve been playing with the idea of dream postcards – fragments of my realm of dreams and imagination shared as glimpses into the rich and often complex inner world that is me. I’m still working on the name – I feel it has to be just right to work.

I love the concept of this idea, although I have yet to figure out the practical application of it as art.

I’ll get back to you when the idea is a little more fully formed.

Until then, leave your thoughts in my comments…

I am officially the Liberal Democrat candidate for Margate in the Kent County Council elections. Posts where I might talk about politics or the election, or anything tangentially related to that will have the following required notice.

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