Sometimes you want to be the kinds of heroes that are more used to waking up in the gutters than a castle. Here’s how!
We love down and out heroes. These are the kinds of heroes where you raise an eyebrow and go “those guys?” Your Guardians of the Galaxy. Or friends of Peacemaker. Or even the main heroes in the recent D&D movie, Honor Among Thieves. They’re heroes but with a layer of grime on them. They’re not necessarily bad—they’re just having a hard time.
It’s such a delicious fantasy to play into. Some of my favorite games have involved playing an absolute wastrel who gets swept up in whatever the plot is. But D&D, especially, is a game that lends itself to competence. So how do you keep that down and out vibe while still winning? Don’t worry, we’ve got you covered.
Dream Small

Epic heroes have epic dreams. They dream of saving kingdoms. Of finding mythical artifacts that can shape the world. Of slaying the kinds of monsters that give your nightmares nightmares. But grimy, down and out adventurers? They dream small.
They dream of bbeing able to afford a room at a halfway decent inn. Not a good inn. Or even a good room. They dream of not having to pay off the adventurer’s guild every time they take on a job in Waterdeep. Or being able to buy a new sword instead of a used one from the goblin emporium in the undercity.
All that to say, a quick way to get at these kinds of heroes, is to have the most pathetic dreams you can think of. And make them seem out of reach. “One day, I’m gonna get a suit of armor that fits.”
Be Petty

Grimy heroes are often in the same category as criminals and corrupt merchants and other similar types. When you’re hanging out with scum and villainy, you have to give and take your lumps where you can. Which means sometimes you just have to be petty. Did you pull off something that another squad couldn’t? Rub it in their faces.
Taunt the merchants that you know are overcharging you for subpar goods. The whole idea is that what goes around comes around. And at least when you start your adventures off you want a lot to be coming around.
You Can Have Pride or Dignity But NEVER Both

The Guardians of the Galaxy are a great example of this. Early on, they are pulling the worst jobs. And as adventurers who are down and out, you can lean into that nature by taking on the jobs that other adventurers might turn their noses up at. Clearing out the Otyugh nest. Dealing with the Xorn infestation.
If your character thinks they’re too good for a job, that’s a great way to invite someone to prove them wrong. Or, conversely, if you decide that today you have pride, it can come at the expense of doing something morally questionable. Basically as long as there’s a “grimy” feeling to the kinds of adventures you’re going on (at least at first), your party is on the right track.
Hoist Yourself With Your Own Petard

A crucial part of playing heroes like the kinds in Honor Among Thieves is that they just can’t help but get in their own way. Ego comes to bite you in the worst times. Or you decide to make the bad financial decision—invest it all because this time the risk is going to pay off in spades.
A big part of it is knowingly making a decision that logically doesn’t make sense. You invite trouble into the life of your characters because of who they are. Maybe they believe their own lies and take on a job that is maybe too dangerous.
Or maybe they try to abscond with the sacred idol to pawn it in the black market instead of returning it to the Druids—and that can open up a whole other chapter. It all depends on the kind of game you’re playing, but a big part of the “we’re petty low-life heroes” comes from being your own worst enemy.
Leave Room to Grow

Why do we like these heroes? Because when they win, when they finally start to learn their lesson and grow, it feels so satisfying. The important thing is to leave room to grow. That’s where a lot of the other “make it worse for yourself” advice comes into play. If you can have fun wallowing in the mud, then when you finally step out, it’ll feel so narratively satisfying.
A good way to think of that is to find little moments to show your character thinking beyond the petty payoff of the very next thing that will satisfy some need or vice. Maybe you save the orphan and let them go without collecting the reward. It’s a decision that—in a satisfying mirror of earlier—doesn’t make financial sense, but is a nod towards being an actual hero.
Happy adventuring!
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