“Roll a D99” – Brooklyn Nine-Nine & D&D



Brooklyn Nine-Nine is one of the best comedy shows I’ve ever seen. Every episode, two or three main plots develop, with the nine main characters essentially splitting up into groups to tackle their own plot-line. What keeps the show fresh is their strong characters, mixing up which characters interact with which from episode to episode. By leaning on their cast’s strong personalities, they can make an inherently formulaic show avoid feeling monotonous.

It’s the strength of the cast that I want to focus on. If you’re playing D&D, you’re creating a story. By examining what makes stories successful or interesting, you can have the same effect on your game. I think each of the cast of Brooklyn Nine-Nine has a lesson to learn to help you up your D&D game in one way or another.

Jake Peralta – Don’t Be “The Protagaonist”

andyWhen Brooklyn Nine-Nine started, the most common complaint I heard is that people were sick of Andy Samberg and didn’t like his character on the show. The first season leaned heavily on Jake, exploring his need for approval and having him try to impress Captain Holt or otherwise shirk his police duties. I remember people saying that the show was pretty stale, not really breaking any new ground. For instance, Scrubs had already tackled the idea of a goofy white dude in a serious job years earlier.

The show really started to pick up when it stopped focusing so heavily on Jake. He’s still the de facto “main character” of the show, but not every episode revolves around him. Jake is just as likely to be along for the ride in another character’s story. In one episode, Boyle tries to get his son a rare Latvian action figure. In a rare show of competence, Boyle enters the strange world of the Latvian mafia, requiring every one of his unique (and often disgusting) skills to track down the toy. Here, Jake actually plays straight-man to Boyle, empowering Boyle’s story and serving more as commentary than the driving focus behind the episode.

In D&D, the players represent a group of adventurers. They should each have their own stories and goals, overlapping with a common purpose. There shouldn’t be a “protagonist” in any D&D party. A given encounter, session, or story arc might have a stronger focus on one member of the party compared to the rest. Perhaps the party is staying at the manor of one of the player’s noble family, or they are investigating the disappearance of one of the player’s former mentors. A character might naturally find the spotlight because of their or their player’s charisma or strong personality. However always focusing on one character, or focusing on them to the exclusion of the rest of the party, is a mistake. If you find your character getting brushed past or walked over by a Jake, talk to your DM or your fellow players about how to get yourself out there. If you find yourself being the Jake too much, try to find ways to empower other players to contribute.

Rosa Diaz – Be Multidimensional

rosaRosa is a scary cop. She laughs when people are hurt, alludes to owning medieval weapons, and hides every minor detail of her personal life from her coworkers, no matter how small. Every now and then, however, we find out humanizing details about her. She adopts a puppy and immediately falls in love with it. She used to go to school for ballet. In the latest season, we find out that Rosa’s bisexual. The force of that episode involves her trying to come out to her conservative parents, struggling to open up and talk about her feelings. If Rosa was just another angry person, she wouldn’t be as interesting a character. It’s these types of moments that give her depth. These details don’t prevent Rosa from still having her gruff demeanour and cynical worldview, but they give the writers something more to work with and also give the audience a more interesting character to watch.

When making a D&D character, it can be helpful to think of your character in broad strokes at first. I’m going to play the cowardly rogue, the bumbling wizard, or the wisecracking humorous bard. When playing a Rosa, things can get pretty monotonous pretty quickly. A problem arises if you become married to that description. Why not have your cowardly rogue stand up for themselves in an important moment? If your wizard is in danger, why not have them display some competence for once? What makes your bard shut up for a moment and take in the gravity of a situation? If you find yourself playing a Rosa, ask yourself if you can break free every now and then when the situation demands it.

Terry Jeffords – Care About Something

terry.gifTerry is special. Most of the other characters’ families don’t come in much. For Terry, however, his family is brought up almost every episode. Every Terry-focused episode has to deal with his family in some way. He avoids doing field assignments because he’s afraid of leaving his kids fatherless. He deals with his insecurity about getting a vasectomy and whether or not he’s done having kids. In the episode where he is racially profiled, his biggest concern is explaining to his twin daughters the reality of living as a black person in New York.

In D&D it can be tempting to make your character a drifter or loner, with no connection to the world around them. They don’t care about others, having nothing to tie them down. This causes a couple of problems. First, you miss out on a lot of chances for interpersonal character drama. You also have to work harder to explain why your character is working with others or helping strangers. You give the DM much less to work with in designing social encounters. Everyone has to care about something. Why not give your character a family? An organization that means something to them? Even if you want to play the loner card, it’ll be more interesting to have had something you cared about in the past than to have always been an emotionless rock. Just make sure that if you do take this angle, you don’t allow their sad backstory to prevent them from making new connections. A story where someone vows to never love again is only dramatic if they actually then fall in love again. If you find yourself playing a Terry, good job! He’s a precious angel who just needs his yogurt.

Charles Boyle – Don’t be Cool

boyle.gifBoyle is weird. Full stop. He eats weird food, uses uncomfortable phrases, and always has a depressing story. Boyle doesn’t even realize he’s weird or sad for the most part, and this lets the writers have a lot of fun with him. Boyle is proud of all of his weirdness, letting the other characters and the audience feel comfortable laughing at him. If he was a total sadsack with all of this dark backstory, it wouldn’t be funny.

It can be tempting to try to make your character the coolest person in the room. The badass warrior with a cool sword, always saying cool stuff. Cool isn’t the same thing as interesting. I’d much rather have a funny or unique character at my table than someone playing Sonic the Hedgehog wearing a leather jacket. Have your character be the butt of the joke, or be pathetic sometimes, or handles themselves weirdly. Trying to be cool isn’t cool. If you’re playing a Boyle, have fun! Just try not to turn into a Scully.

Michael Hitchcock – Punch Down

yuck.gifHitchcock is gross. Gross like Boyle, but in different ways. Hitchcock says gross things about people. He hates that they have safe search at work. He only watches the porn parody version of movies. He knows a weird amount about feet.

In D&D you might want to play a character with an off-colour personality. First, make sure that your group is comfortable with this. Everyone, not just the DM, has to be on board with you playing a character, for instance, who really hates elves, or talks about sex stuff, etc. If your group is cool with it, and you’re for some reason committed to doing this, there’s still better or worse way to go about it.

In comedy there’s something called punching up or punching down. Essentially you should ask yourself who is the target of the joke. Punching up means taking those in power down a peg, such as through making fun of politicians. Punching down is making fun of those with less power or social capital, such as by insulting marginalized groups. When Hitchcock does or says gross stuff, it usually isn’t framed as acceptable. The show goes out of its way to say Hitchcock is a bad person for doing or saying it, and he always gets his comeuppance. If you do feel the need to play a Hitchcock, make sure you’re not framing their actions in a way that endorses their behaviour. You have to be prepared for your character to lose, every time.

Or better yet, don’t play a Hitchcock. ¯\_(ツ)_/¯

Captain Raymond Holt – Less Is More

sprinkle.gifCaptain Holt is one of the funniest characters on the show. Incredibly stoic, serious, and stuck in his ways, Captain Holt can get laughs with short sentences or even just a facial expression. I’d wager that Holt has the biggest laugh-to-word of any of the cast.

Some people think that having a charismatic D&D character means being super assertive, seductive, and talkative. Good roleplaying is giving long speeches and soliloquies, right? Sometimes the most interesting characters can be those who speak little, knowing just the right time to contribute. You don’t need to be the loudest person at the table to have a profound impact on the game’s story or the group dynamic. Be careful when playing a Holt; the Jakes of the world might stop you from getting a word in edgewise. Know when to assert yourself.

Amy Santiago – Control Issues

coca.gifAmy’s a huge stickler for the rules. She reads up on things other people find boring, and keeps things meticulously organized to a fault. She has trouble letting go, and can’t stand idly by while others break the rules. She tries to change the behaviour of others around her so that they act on her terms.

Try not to be an Amy.

In all seriousness, there’s a big problem with players who try to play the whole party or police their actions. You should stick to yourself, and don’t try to ruin other people’s fun. If you do find the other players going off rails and “ruining” the game, but everyone’s having fun, then you’re the odd one out.

If you have a problem with other character’s actions at the table, talk to your DM or the other players out of character. Never try to resolve external game drama in-game. Amy is entertaining as a character because she ultimately can’t control herself or others. It’s funny to watch her have to deal with a world that doesn’t work like she wants. If you want to play an Amy, make sure that you’re not trying to have other characters actually stifled in their options.

Gina Linetti – Exaggerated is Better

gina.gifGina isn’t just a bit over the top. She’s completely over the top. In the show, she started as a lazy employee with some weird interests. By the latest season, she has a supernatural ability to always be right and manipulate people. Her character underwent what is often called Flanderization, where a character’s attributes become exaggerated as a show continues. This happened with a lot of characters on the show, but I personally feel like it hit Gina the hardest. Notably, exaggeration doesn’t have to be a bad thing.

Feel free to double down on the things that you feel makes your character interesting. If something silly happens at your table, double down on it and make it part of your character. Don’t be afraid to commit to an idea rather than nipping it in the bud. By exaggerating your character’s quirks, you give the other players and the DM more to work with. Be careful with being too much of a Gina. If the world can’t handle you at your Season One Gina, they don’t deserve you at your Season Five Gina.

Norm Scully – Don’t be Norm Scully

scully.gifScully is useless. He makes people grossed out and uncomfortable and can’t do his job properly. Stories on the show rarely involve Scully as a main character, and when they do it’s more about those around Scully trying to work around him. While Scully and Hitchcock have become bigger parts of the show as the seasons have gone on, they haven’t really had any development.

Scully would make a fine NPC. As a character though… It would be pretty annoying to have a Scully at your table. While you want your character to have flaws and you need to understand that you don’t have to be the coolest character at the table, something bad happens if the pendulum swings too much in the other direction and you force your character to be unlikeable and useless. Unlikeable and useless people exist in the real world, but they don’t really make for compelling stories. Or at least not the ones that D&D works best with.


D&D isn’t a game in the traditional sense. It’s not about the result, but the journey. It’s not about winning or completing a certain goal. At the end of the day, it’s about entertainment. You should be entertaining to yourself and your fellow players. It might be worth it to examine the media you like to see what you can add to your own games. Compelling stories usually need compelling characters, so taking a look at what makes your favourite characters so enjoyable can help you make your games better as well.

Want help making your first character? Check out my Guide on the subject!

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