Monster of the Week The Crooked Class Guide

In a modern world full of monsters and magic sometimes it’s good to have someone Crooked on your side to tilt the game in your favor. The Crooked class in Monster of the Week is a fun class that gives you a wide variety of options when it comes to backgrounds, specialties, and the particular brand of trouble you have in your background that might spill out to the rest of the group. In other words, if your idea of a fun time in Monster of the Week is being a very useful character spliced with chaos goblin then you may have found your perfect class!

Yeah, I’ve been around the block. A bit of this, a bit of that. When I came across the secret underworld of monsters and magic… well… it wasn’t so different from the underworld I already knew. It was easy to find an angle, just like before.

The Crooked, p.35 Monster of the Week Manual

Monster of the Week is our modern world but with monsters and the supernatural existing in many forms.

Monster of the Week The Crooked Playbook picture

Often taking an episodic and literal “Monster of the Week” format, these can be disassociated incidents or part of a larger plot as some major event is revealed as being an “Uh-Oh” type of moment over a longer campaign.

The Crooked is one of multiple classes available and this is just like it sounds like.

The Crooked is the roguish, legally questionable, probably criminal (or at least gray area) member of the group who understands the vital importance of the difference between what the law says you can and can’t do and what you actually can and can’t do in the real world in any given moment.

This is a fun class that can be built in many directions, so let’s take a dive into Crooked and see how this class stacks up, if it’s a good play, and if it’s the right one for you in your next Monster of the Week game.

What Type of Crooked Will You Be?

The decisions on the Crooked class in Monster of the Week starts out right away.

You get several beginning ratings that reflect the overall traits you want your type of Crooked to be, which is fantastic since this opens up the back stories you can realistically make up (and match with your starting stats accordingly) in a convincing in-game way.

The Crooked Ratings for MOTW are:

  • Sharp Build 1 – +2 Sharp, +1 Cool & Charm, 0 Tough, -1 Weird
  • Sharp Build 2 – +2 Sharp, +2 Cool, 0 Tough, -1 Weird & Charm
  • Charm Build 1 – +2 Charm, +1 Cool & Sharp, 0 Tough, -1 Weird
  • Charm Build 2 – +2 Charm, +1 Sharp, 0 Cool, -1 Tough & Weird
  • Tough Guy – +2 Tough, +1 Sharp & Cool, 0 Weird, -1 Charm

Whether you want to be Charming, Cool (under pressure), Sharp to notice every detail, or a Tough guy will affect which of these lines are going to be best for your Crooked build and go hand-in-hand with which Background you decide to choose. After all, the skills needed by a Grifter will be completely different from a Burglar or a Hoodlum.

There’s a good variety here and it makes sense Weird would be the dump stat as the Crooked tend to stumble into this world as opposed to have studied their way via conventional study or occult methods.

The Crooked Backgrounds

There are many different jobs and needs in the criminal underworld, and it makes sense with so many angles to play that you would get plenty of choices for backgrounds. Here are the backgrounds from Monster of the Week for the Crooked Class:


You are a tough guy all the way. Bouncer, Soccer Hooligan, guy/gal who collects “protection” payments because it would be a shame if something happened to this nice shop you have, you’re tough and everyone knows it. You’re willing to get into a rough and tumble fight, and you likely have the experience to back it up.

Story-wise, this also creates some interesting “Heat” moments with the prompts given that might have you on the wrong side of a big baddy, a police detective who doesn’t like you, or a rival who never got over not being able to take you down in the illegal cage fights.

Recommended Build: Tough Guy, of course. Being able to replace Charm with Tough when it’s intimidation time means when you need a brute force hammer to get into places you don’t belong, the Tough Guy Hoodlum becomes quite a powerful build!


Ah the Burglar. The Burglar gets to roll a +Sharp roll every time they break into a new location, and on a 10+ you get to choose 3/4 possible benefits, while on a 7-9 you get to pick 2/4 benefits.

The 4 Burglar Benefits

  • You get in undetected
  • You get out undetected
  • You don’t leave a mess
  • You find what you were after

In other words, your experience with sharp eyes and haggling with many fences means you know how to find what you want and often times can do it clean. There may or may not be a mess afterwards, but if you get what you need and mostly undetected it’s not all bad, right?

While this might seem a bit underwhelming if you’re used to the Rogues of D&D, keep in mind that most MOTW episodes are Mysteries. Having a Burglar who can find what you were after or get into a place you might not otherwise be able to break into can be incredibly useful when

Recommended Build: One of the +2 Sharp builds for sure. I’d be inclined to take Sharp 2 because that coolness under pressure will be useful when the dice betray you and things go sideways, but there are good arguments to be made for going the other direction, as well, depending on how the group is likely to back you up.


Master of the con, a grifter knows how to evaluate a potential target and see what it takes to manipulate them. If you pick the Grifter, anytime during a Mystery when you are looking to manipulate someone you can ask the Keeper what it would take to get the target to do what you want. The Keeper must tell you honestly, though they don’t have to answer completely.

In other words, you have some serious insight into how to charm someone into helping out your group – whether they were inclined to do so or not. Or possibly manipulate them in some way – whatever the situation warrants.

Recommended Build: Either of the Charm ratings are an excellent foundation for creating a Grifter build for your Crooked character.


Every group needs someone who knows how to get things. And as a Fixer, you tend to know how to get unconventional, rare, illegal, or even mystical items. In any situation where you need to buy something, sell something, or hire someone you get to roll +Charm. On a 10+ you have the perfect connection. On a 7-9 you know the only person who can do it, but there’s a complication, though you get to pick the complication (You owe them, they screwed you over, you screwed them over).

On the other hand if you miss the only person who can help is someone you know, but they hate you. Maybe send someone else in the group to help at that point?

Recommended Build: Either charm option works well, as the negatives to both aren’t really going to heavily affect a Fixer build of the Crooked.


And here’s the nastier potential side of the Crooked. Their boost is simple, but devastatingly effective: a +2 Harm when you take your first shot at an unsuspecting target. For those of you not familiar with the MOTW system, 2 Harm is considerable. 4 Harm moves normal humans from Okay to Wounded and sliding towards Dying and chances are with any weapon you have as assassin, that first hit will be 4+ Harm.

Recommended Build: Tough or either Sharp. Since Tough is a general stat that is the one I’d go with in most cases, but see if your Keeper is going to make firearms or certain weapons run off a different stat like Cool or Sharp. It’s not likely, but it is possible. Tough doesn’t have to be a big bulking brute – maybe you’re deceptively capable while being benign looking.


In a world of magic, it’s so tempting to play a Crooked who wants you to think they’re using magic when they’re not. The Charlatan rolls +Cool that allows you to manipulate people as a fortune teller learning what they want most, or amazing and fooling an audience with your “magic.” This is a super interesting pick and one that is going to have major roleplay potential.

Why be a Grifter when you can be a Charlatan?

Recommended Build: The Sharp Build 2 which is the only one with +2 Cool, which plays to your ability to play in front of a crowd or in a tight situation.


Pickpocket…it’s a classic choice. When you’re stealing something small, roll +Charm. If you hit 10 or more you get it clean without anyone noticing. On a 7-9 you don’t grab it, get the wrong thing, or they remember you later: you’re choice.

This lets you put your sticky fingers to work for the group, and to decide in those critical moments if it’s better to not make the pick, or to know someone will be coming after you later.

Recommended Build: Either Charm build 1 or Charm build 2 will work depending on whether you want to be cool when trouble hits on a missed pickpocket or a little bit tough.

The Crooked Playbook Monster of the Week

What Do Crooked Moves Bring To The Table?

Unlike the Chosen class, the Crooked class doesn’t have any required moves. They have a quite a variety of different builds just based on the backgrounds, and that’s before diving into the Class-specific moves.

The Monster of the Week Crooked Class has eight unique moves they can choose from. We’ll give very brief summaries of each however it’s worth noting that because you can look at the free PDF online, it’s not hard to get the full description of each.

But let’s take a look at the moves that the Crooked gets to choose from for Monster of the Week! Initially you get two of these moves, and through leveling up can end up with up to two more.

  • Artifact: You “Found” a magical artifact – heck maybe this even led to your knowing about the Supernatural. This Artifact can be Protective (+armor), Lucky, Grimoire (+magic), Skeleton Key that opens any magically sealed lock, or an Imp Stone (summons a weak demon). This Artifact can be extremely useful for investigating all sorts of mysteries.
  • Crew : You’re important enough to have your own crew of 3-4 people who are willing to help out with just about anything.
  • Deal with the Devil: You sold your soul to the Devil, and out of it you got 2 of the following: Wealth, Fame, Youth, Skill, or Sensual Gratification. Payment is still due, which could make things interesting…
  • Friends on the Force: It’s easier to get away with things when you have a few friends on the force willing to look the other way…
  • Made: You’re a made man. You can call for help from fellow made men, who do expect payment, and you get a little extra protection but sometimes the bosses will have a request…and you had better not say no!
  • Driver: Get +1 when driving, you own two vehicles, and you can hotwire just about anything.
  • Home ground: Your crew goes out of the way to keep the locals happy, and that means when you’re back in the old neighborhood you can find a place to hide or people to help you with minor favors, no questions asked.
  • Notorious: You have a reputation from your criminal past. When you reveal who you are the terrifying reputation you carry with you counts as a reason for people to do what you ask or to manipulate them…but throwing around your reputation too much will bring the heat from both lawful and unlawful, and possibly even supernatural, forces.

As you can see, there are plenty of options for how to build the Crooked, and the combination of Backgrounds, Moves, Heat, and Ratings tell you that you could play several different Crooked characters and have very different experiences and play styles in doing so.

Monster of the Week TTRPG Books
Our Sunday group has absolutely fallen in love with this system – and several of us bought the books to support the publisher but many of the rules and fillable character sheets are available for free in PDF form online from the publisher themselves – classy move, Evil Hat, and we like it!

Who Should Play The Crooked in Monster of the Week?

If you like being a con man, a morally questionable face, someone with connections, or delight in being the useful party member who brings chaos to the group via backstory, or just general fans of the true anti-hero trope, then Crooked might be the class for you. They are certainly one of the most versatile classes in the game as you can do so many builds with them and specialize in a wide array of skills.

This is a class that is going to have a lot of fans, and because of the many different forms an underworld associated scallywag can be built, it wouldn’t surprise me to hear about some players falling in love with this profession and playing multiple styles of the Crooked class just to see everything that it has to offer.

Because of the versatility of this class, it’s going to appeal to a lot of people. Basically the only thing it doesn’t do particularly well is magic, so if you’re interested in a magic build you will want to go in a different direction otherwise this is a class with a lot to offer.

Why Old Man Callahan of Assorted Meeples Loves the Crooked Class

I love the idea that there’s this guy out there that’s shady as hell, Probably should be in prison, but he’s realized that there is horrible shit going down that can end the world. And he draws a line.

This kind of bad is ok by my code, this kind is not.

I like a hero that’s willing to get a little dirty to keep the playing field level.

Callahan on why The Crooked class spoke to him in Monster of the Week

There’s some first-hand insight from a Meeple who is currently playing The Crooked on why he personally digs the class, and burglar has come in very useful so far…though a bit terrified to see how the Crew turns out. I’m feeling a lot of Three Stooges vibes there.

MOTW The Crooked Class, In Conclusion

Some classes only have one or two main options to build into, and that’s not necessarily a bad thing. The Spooky Class has been a blast to play despite working best as one of two builds – a clear A/B choice, which the Chosen kind of feels like, too. The Crooked class has a lot more options and allows players who like to play a Jack of All Trades or Skill Monkey build to really thrive within in the group.

There are many systems that don’t allow that non-specialized build to thrive, and finding one that allows a generalist to do well is a fresh breath of air, and the Crooked class is a fun option that is going to go well with many TTRPG players, even those who did not traditionally play rogue in 5E D&D.

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