D&D: Low Level Adventures For Morally Questionable “Heroes”

Need some low-level adventures for a party of down and out “heroes” with questionable morals? We got you covered.

Hey, sometimes your player characters aren’t “heroes” so much as they are “hired thugs” with “questionable codes that they maybe follow.” And that can be a lot of fun. Or maybe only some of the party members are scumbags—but every now and then you gotta throw the slimy heroes a bone too. So here are some low-level adventures for the shadier side of the alignment grid.

Rig a Contest For a Noble

All you need for this adventure idea is a noble with designs on winning some contest or another. It doesn’t really matter what that contest is. You might think you’ll have to figure out rules for running a tournament or the like, but trust me. All you need is someone to offer a good chunk of money in exchange for making sure that either they win or a specific person loses.

And typically the latter option lets player characters be more creative. Because then all they have to do is stop someone from competing. But either way, there’s so much room for player characters to try and figure out how to either keep a rival from entering the contest in the first place, or how to rig it in favor of the noble. It starts with petty crimes and will probably escalate to kidnapping and intimidation much faster than you’d expect.

But really, this can be a good one to see where your players heads are at when it comes to baseline “adventure villainy.”

Kidnap a “Pet”

Another way to dabble in the rich palette of shades of gray out there is to kidnap a beloved pet from someone. There are plenty of ways to make it dangerous and potentially back-biting for the wretches who decide to take up the quest. Either the “pet” could be something dangerous like a Gray Render or an annoyance like a Rust Monster.

Or else the person they’re stealing from could be incredibly dangerous. I mean after all, kidnapping Sylgar from the Xanathar is a surefire way to earn the unending enmity of an aberration from beyond your dreams. Of course, you don’t have to know you’re kidnapping the Xanathar’s gold fish to start—just that all you have to do is get a fish and then get 5,000 gold pieces. Simple. Easy. Who would turn it down?

The real fun can come in deciding what to do once you learn the truth about what the adventure ACTUALLY entails.

Waylay the Mercenaries

And sometimes you just get to be the low-level thugs that happen to someone else. An adventure like this can lean into the stereotype of adventurers being dangerous people who will stab you in the face just so they can take your stuff. To that end, instead of being hired to protect something, they get hired to stop folks. Waylay a group of mercenaries on the road.

And you can go a couple of different ways with this, depending on how shady you want to be. You could waylay a group of even more explicitly evil mercenaries (for the feel good story of the year, if they can actually manage to beat them), or maybe they learn that the mercenaries the PCs have been sent to waylay are actually an order of noble heroes there to prevent the villain of a low-level adventure from carrying out their wicked scheme.

And if you’re sensing a theme of “and then the players have to decide what to do” you’re right—and that’s part of what makes these grimier adventures so much fun to play around with. Again, if that’s what folks are on board with.

Repossess the Crystal

Repossessing something is already kind of a villainous thing in and of itself. You’re putting the interest of money over the interest of someone who’s using it. But what happens when you’re supposed to take back the scrying crystal from the local tyrant-wizard who has fallen behind on their payments to the Arcane Guild. Or if you need to reclaim the healing crystal when the Healing Mage Order decided that this town was no longer going to be in-network.

I especially like the idea of an adventure where you’re working for a business that lends magical artifacts to evil wizards – because it’s a whole lot easier for people to be villainous to villains. You can really get into the grime and muck of the adventure if your whole deal is that you need to take back the scrying crystal from an evil wizard who just doesn’t want to pay the shadowy Arcane Guild a monthly subscription anymore. Magic used to be free, you know. Etc.

Collect the Protection Money

And finally, collect the protection money. A tried and true simple adventure. All you have to do is go to NPCs and demand that they pay the money they said they’d pay. Again, it’s another chance to “be villainous to villains” especially if there are some merchant NPCs who have crossed the party in some way or another.

But one extra wrinkle you can add to an adventure like this is the inevitable moment where they have the money. It’s in their hands. Are they really just going to hand it over? There are so many options to consider. Like taking the money and running away.

Once you get people thinking, though, then you’re roleplaying on the shadier side of things for sure!

Happy adventuring!

Bell of Lost Souls Staff Writer and DM, J.R. covers RPGs of all stripes and on occasion eats sandwiches. You can ask him about either at [email protected]

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