Have you ever wondered it would be like if the characters from The Office got a D&D game together?

With so many hilarious (and, frankly, chaotic) characters, I’m sure it would be quite the experience!

So while we never got to see the staff of the Dunder Mifflin Paper Company rolling for initiative or storming caves of goblins in search of treasure, we got to know the characters well enough that we can take some guesses at how their game might go.

I figured we’ll take a break from the usual player guides, DM tips, and what not to answer a burning question:

What would it look like if the characters of The Office played D&D?

Michael Scott

Character: N/A (Dungeon Master)

Goofy and eternally inept Regional Manager of Dunder Mifflin’s Scranton branch, Michael Scott is the office’s Dungeon Master.

Going down a YouTube rabbit hole, he stumbled across videos of people playing the game. Seeing how the players would joke around, do voices, and have adventures, Michael knew he wanted to try playing.

So he decided to wrangle everyone in the office into playing with him.

Michael doesn’t realize just how much goes into running a 16-person D&D party but figures it will be fine. He started to read the Player’s Handbook but ended up just looking at the pictures.

“It’s just like my improv classes!” he figures.

In game, Michael loves the attention from the players when he’s describing scenarios. This leads to him constantly trying to make even the most basic actions (like ordering a round of ales at the tavern) into something explosive and dynamic.

To make everyone like him more, he has a tendency to overload the party with ridiculously powerful magic items. As a result, everyone in the party has low level characters equipped with high-tier magic items.

His games make virtually no sense but are also oddly engaging. At times, they even have a tendency to pull at the heart strings.

Dwight Schrute

Character: Red Dragonborn Sorcerer/Paladin/Warlock Multiclass

Dwight shows up fully in costume with real, functional weapons.

His character has been perfectly optimized and he has written a 20-page backstory about the character’s adventures thus far.

Dwight insists that his character is the leader of the party, but only Angela seems to support that claim. He has also given himself the title of “assistant DM” though Michael regularly corrects him as being “assistant TO the DM.”

In his excitement, Dwight has a tendency to try to play other peoples’ characters. Other than that, he’s really good at moving the story forward (even if it makes him a bit bossy at the table.)

Jim Halpert

Character: Dwarf Berserker Barbarian

The Scranton branch’s favorite slacker, Jim, didn’t want anything to do with the game at first. It was only when he saw how excited Dwight was that he decided to join the game.

Jim wanted an easier class to play so he made a Dwarf Berserker Barbarian which he named “Dwight.”

In the game, Jim frequently says things like “Dwight isn’t smart enough to help the party” or “Dwight is WAY too short to reach that item” just to needle the real Dwight.

But Jim eventually starts really getting into the game, especially because Pam is doing the same. He won’t change his character’s name, but he eventually lays off of the shenanigans… somewhat

Pam Beesly

Character: Half-Orc Devotion Paladin

Pam is reluctant to play at first but finds herself getting HOOKED by the end of the first game.

More than anything, Pam wants to be taken seriously at the table. So she made a character that nobody expected from her to show everyone “the real, confident Pam.”

She really engages with the story and helps keep the group coordinated and together. She takes detailed notes about each session and emails recaps to everyone.

Before each game, Pam sets up the table and helps Michael bring in his huge box of props.

Ever the artist, Pam spends a lot of time drawing scenes from the game in her sketchbook. She’s drawn everyone’s character and started a scrapbook of the branch’s D&D adventures.

Toby Flenderson

Character: Human Assassin Rogue

Toby genuinely wanted to play and figured the game could be used as a team-building exercise. He even had the idea to write the time off as an HR expense.

Initially, Michael refused to allow Toby to play but finally caved after everyone else demanded that Toby be allowed to join.

Toby’s character died within the first 2 minutes of the game when Michael had 20 liches attack only his character in the starting tavern.

When Pam told Toby he can just make another character, Michael insisted that the liches sat at a nearby table talking about what they would do to the next person who walked through the tavern’s door.

After a brief staring contest with Michael, Toby said he had an assignment from the home office he should be working on and went back to his desk.

Kevin Malone

Character: Kenku Evocation Wizard

Kevin insisted on making a Wizard even though Oscar kept insisting that it would be too difficult for him to play. When choosing his character’s race, Kevin made his character a Kenku because “it has a K like Kevin.”

Despite never playing before, he constantly uses his spells in creative and efficient ways. Kevin’s character has saved the day in numerous tough situations that the party has found themselves in.

He might roll a few “kelevens” but he makes it happen!

Oscar Martinez

Character: Human Divination Wizard

Oscar hasn’t played D&D since college but finds himself getting into it.

Before the game started, he got the Player’s Handbook and read the entire thing from cover to cover. He tends to be a rules lawyer and gets frustrated when Michael keeps ignoring the rules.

Oscar made a Wizard in hopes that he could show Kevin how to play the class properly. He specifically chose Divination “to hopefully save us if Kevin does something that will blow us all up.” Instead, he ends up taking notes from Kevin’s ingenious use of spells and tactics.

Oscar will probably start his own (more rules-focused) D&D group in the near future. He will not be inviting his coworkers.

Angela Martin

Character: Tabaxi Life Cleric

Angela refused to play at first. She insisted that D&D is evil and a waste of everyone’s time. However, she changed her mind when Dwight showed her the Tabaxi race.

She named her character Sprinkles after her cat.

Angela’s tendencies as a control freak in the office are in the game as well. She enjoys being needed and having control over the party with her character’s healing abilities. If someone is challenging her, she won’t heal them and insist that she’s out of spell slots.

Her character has an ongoing feud with Phyllis.

Phyllis Vance (Lapin)

Character: High Elf Peace Cleric

Phyllis also made a Cleric even though Angela insisted that “we don’t need another one.”

Phyllis is quick to heal and buff members of the party who like her more than Angela. When she heals another character, she makes passive remarks like “don’t forget that I’m the one who healed you” and “aren’t you glad I saved my spell slots?”

Her character has a husband NPC in the game, a frost wizard named Vance. She brings this up in most conversations and assures people that he’s very well-known.

Stanley Hudson

Character: Human Champion Fighter

Stanley has no interest in playing but happened to already be sitting at the table and refused to move. Insisting that he had to play if he was sitting at the table, Dwight made Stanley a character.

Stanley stays in the game because he learned they’re being paid extra for “training time” since this is a “teambuilding exercise.”

At first, Stanley’s character didn’t do much as Stanley was spending the game doing his crossword puzzle. When asked what his character would do, he’d give answers like “shoot a fireball” or “whatever everyone else is doing.”

Dwight got frustrated and now plays Stanley’s character in addition to his own.

Stanley is perfectly fine with this.

Andy Bernard

Character: Gnome Lore Bard

To prepare for the game, Andy watched clips of Critical Role and decided to play as Scanlan Shorthalt. He insists that this is his original character.

Andy insists on performing in real life and begins every turn by playing a full song on his banjo unless he’s interrupted.

The group was planning to have a conversation with Andy about this behavior, but things more or less worked themselves out. After rolling three natural 1’s in a row, Andy lost his temper and smashed his banjo against the wall.

He’s currently away at Anger Management Counseling.

Creed Bratton

Character: Tiefling Mastermind Rogue

Creed stumbled into a LARP group in the 80s and didn’t realize the people there were in character. He was a member of the group for 4 years. Getting this game together in the office has reminded him of these events.

He now believes that everyone in the office are actually elves, wizards, etc. incognito.

Trusting his keen survival instincts, Creed makes a character to blend in with the game. He is secretly trying to turn everyone on each other so he can make an escape in the confusion.

Meredith Palmer

Character: High Elf Drunken Master Monk

Meredith misunderstood the use of the word “party” but is just going with it now.

She insists that she’s “just playing my character” when she takes a shot of whiskey at the start of each of her turns.

In the first half of each session, Meredith’s character is great at engaging with the story. In the last half, she’s mostly silent except for jumbled, incoherent ramblings.

When asked why she chose to be an Elf, she said “what? Elves are hot!”

Kelly Kapoor

Character: Aasimar Glamour Bard

Kelly thought the game would be a great way to make Ryan like her more. She made both of their characters.

Her character is “absurdly hot, like everyone is just always like ‘how is she so hot?’ and she’s also really rich and everyone just loves her so much but she’s looking for her Prince Charming, you know?”

Kelly spends most of the game trying to have her and Ryan’s characters fall in love with each other.

When Ryan doesn’t engage, she starts flirting with other characters and NPCs to get his attention. It doesn’t usually work.

Ryan Howard

Character: Wood Elf Hunter Ranger

Kelly made Ryan’s character and modeled it after Legolas. She also named the character Orlando Bloom. It’s a bit weird, but Ryan doesn’t particularly care.

Ryan spends most of the game on his phone at first, but eventually starts to really get into it. He’s convinced it’s some really underground type of free-form storytelling that nobody else has heard of.

He plans to start a D&D podcast now, but we’ll see if he does. (He won’t, but he’ll talk about “the idea” of it constantly.)

Darryl Philbin

Character: n/a

Darryl can’t believe how much time everyone is wasting “playing pretend” while the warehouse crew is sweating and working hard to ship out orders.

He refuses to play and gets visibly more irritated as he’s trying to keep the office running by answering phones and responding to emails.

When the game starts to get more popular, he considers trying to join.

However, he realizes that he’s able to get his work done much easier without everyone constantly interrupting him. This gives him more time to work on studying for business school.

Gabe Lewis

Character: Drow Great Old One Warlock

At first, Gabe wasn’t welcome at the table but said he’ll be reporting the game to the home office if they didn’t let him play. He insists on sitting unnecessarily close to Erin during the game.

Gabe quickly starts making everyone uncomfortable as his character is a weird combination of the 200+ horror movies in his collection.

As it turns out, Gabe watches a lot of “body horror” films. Long descriptions (often involving tentacles) seem to come up from him in nearly every game.

Despite his character’s unsettling actions in the game, everyone reasons that it’s easier to “just deal with it” and stays silent.

Erin Hannon

Character: Halfling Circle of the Shepherd Druid

Erin chose to be a halfling because they seem so happy in all the pictures. She chose her class because being a Druid meant that she could turn into all kinds of cute animals.

She’s technically using WAY more uses of her Wild Shape than she has available, but nobody is saying anything.

“I’m a cat! Now I’m a puppy! Now I’m a fox! Now I’m a… BIG PINK HIPPOPOTAMUS!

She’s not choosing particularly useful Wild Shapes, but she’s having so much fun that nobody (except Dwight) has the heart to say anything.

Robert California

Character: n/a (Dungeon Master)

When Michael moves away, the team wants to keep the game going. So they put out a “players wanted” ad. They were initially looking for another player, but Robert California just laughed and said “roll initiative.”

Nobody knows why they just started going along with Robert’s game, but they did.

Robert’s story has some genuinely good points, but it can also get oddly tense and creepy at times.

Mixing pointed observations about each player into his games, nobody ever really knows if Robert is talking to them or their characters. He particularly has a tendency to raise his voice at Andy both in-game and out of it.

Nearly every session sees Robert introducing new, shallow NPCs with the explicit goal of adding “romance” to the game. Everyone has collectively made it a priority to not engage with this under any circumstance.  

Conclusion – The Office Plays D&D

I really wanted to fit some other characters into this article but didn’t fully know what to do with them.

Holly Flax, Jo Bennet, Nelly Bertram, Todd Packer, and Jan Levinson were all very close to appearing on this list.

What do you think? What would those characters be like in a D&D game? Any characters listed that you think would play differently?

This whole thing started as a funny conversation that had me laughing so hard, I had to make it a thing. I’d love to read some new ideas in the comments!

Want more laughs? Check out what happened when I had an A.I. make a D&D Villain!

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