Mimics and kobolds and owlbears, oh my!
On Dungeons & Dragons and getting back to the playground.
Hey team.
After months now of making excuses for not writing more often, I have come to accept the reality that my life is my life. Changes will have to be made if I want to do this more often… BUT I also like the idea of longer pieces sent every once in a while rather than shorter pieces sent all the time. We’ll see how it goes. I have no shortage of inspiration, only hours in the day.
Anywho, the past two newsletters have been quite… moody? So as a reward for enduring my emotional venting, today I wanted to write about something that just fucking rocks: Dungeons & Dragons.
Ohhh yeah, baby. We’re gettin’ nerdy. Keep reading and you might wanna get a little nerdy, too.
“So, like, how do you win?”
Oh, my child… My beautiful, stupid little child. There is no winning this game. In fact, there is so, so, so much losing.
That’s because any tabletop Role-Playing “Game” (yes, there are many) isn’t really a game. It’s a story. And stories aren’t won—they’re told. Rather than pitting players against each other or a computer program, Dungeons & Dragons (D&D) challenges everybody at the table to do a simple task: make up an interesting story together. There is no winning unless you create something to win; there is no losing unless you create something to lose. It is all made up. There are no stakes except for those which you raise.
At a high level, Dungeons & Dragons is “played” by telling a story—much like sitting around a campfire, only everyone gets to participate. Think of it as a choose-your-own-adventure book meets an improv show. One person serves as the Dungeon Master (DM), setting the scene and narrating the world. The rest are players (or “Party Members”), who role play as characters and make decisions that guide the story’s direction over the course of a campaign. Some campaigns last a few sessions; others stretch on for years. The game “ends” when the story ends or, more often, when scheduling becomes too difficult.
This is what we call emergent storytelling: a living, collaborative narrative written with every decision you make. You can try to plan the ending, but the journey always takes precedence. It’s a boundless but structured role-playing simulation shaped in real time by each participant.
Here’s how it works. The DM begins by creating an original world from scratch. It might resemble the mythical lands of Westeros, the icy tundras of Hoth, or the dusty deserts of Tombstone. Maybe it’s some strange genre-bending fusion of all three. The point is that it doesn’t have to involve literal dungeons or dragons. Then, the DM will add texture: usually some loose notes on the culture, politics, landscapes, and people who occupy the world. However, lots of these details end up being created on the fly, no matter how much energy is invested ahead of time. The world is truly built as you go.
Once the imaginary playground is built, it’s time to explore it. Players then create their characters—fictional identities complete with backstories, skillsets, and physical descriptions—to role play. Each character is built from two main taxonomies: class (barbarian, wizard, cleric, etc.) and race (human, elf, tiefling, etc.). These choices define your abilities and evolve as your character levels up, usually at the DM’s discretion. Importantly, each choice also comes with tradeoffs, because great characters are defined just as much by their fatal flaws as their signature strengths. In fact, being bad at something can help you tell a better story.
Here’s the part that trips people up: none of this is physically grounded. There’s no board. No pieces. Maybe a map if you're feeling fancy. The entire game plays out in your collective imagination—tracked with pencil, paper, and one critical tool: the dice.
Every action’s outcome hinges on a die roll (usually a 20-sided one). Your character’s stats let you modify that roll and therefore the chance of success. The higher your stats, the more the odds shift in your favor—like a handicap in golf. For example, having high Strength means your character will do better on Strength-based rolls, and therefore be strong; high Intelligence means you’re smart; high Charisma, persuasive; and so on.
But that’s enough of the rulebook. The way best way to learn is by doing, so let’s just play.
(You can also watch this viral clip in which very-serious-tough-guy actor Jon Bernthal similarly learns what D&D is in real-time from professional DM Deborah Ann Woll. It’s a real treat.)
You are walking through a dark forest, a bow strapped to your back and sword sheathed at your side. You have just survived an attack by traveling bandits and, by the luck of the dice, barely escaped with your life. Just beyond the brush, you hear a twig snap.
What do you do?
“Uh… I stop and look around?” you say.
Great, make a Perception check!
You’ll then roll your dice and add your Perception modifier. Let’s say you roll a 14 and your modifier is +3 because, let’s say, you grew up in forests like this. That gives you a 17 (well done!).
You look deeper into the forest and see a glint of white fur—or is it feathers?—in the moonlight. After a moment of baited breath, a massive Owlbear comes rushing out of the brush, rears up in front of you, and pounds its chest in a ferocious, territorial display of strength.
“Wait—what the fuck is an Owlbear???”
Great question. Make a History check!
You roll your dice again. You roll a 3. And, because your character has very low Intelligence (maybe they didn’t go to school because they had to take care of their siblings as a child), you actually have a -1 History modifier, giving you a 2. Yikes.
You have no clue what this thing is. It has the head of an owl but the body of a bear larger than any you’ve ever seen. As you stare at it in horrified confusion, it paws at the ground and snarls, preparing to charge.
What do you do next?
If you just answered that question in your head, congratulations. You’re playing D&D.
Or, maybe you didn’t answer in your head because you’re too busy laughing at how silly all this is. If that’s you—good! Keep laughing, because you’re going to love this next part.
D&D is a multi-billion dollar industry. Yes, billion with a b.
That’s just the estimated value of the game itself, originally created in 1974 by Gary Gygax and Dave Arneson and now owned by Wizards of the Coast (a subsidiary of Hasbro).
Add on top a blockbuster like Dungeons & Dragons: Honor Among Thieves which grossed $208 million worldwide in 2023; or a video game like Baldur’s Gate 3, which is estimated to have made $447.5 million in that same year. Add on top of that the millions of dollars made by streaming companies like Critical Role or Dimension 20, which produce live D&D campaigns with, yes, professional D&D players. And add on top of that the merchandising, brand deals, and various other perks of digital influencers. These companies and their lovable casts are so popular they’ve taken their gameplay on the road: this year, Dimension 20’s signature crew played a sold-out D&D session live in Madison Square Garden—and I would have gone if I hadn’t lost the lottery they instituted because so many people tried to buy tickets at once.
Zoom in, and the local impact is just as impressive. Brooklyn game shop The Last Place on Earth made $110,000 last year by hosting community D&D nights, effectively rescuing the business post-pandemic. Meanwhile, a small cottage industry has formed around freelance DMs who run campaigns as part-time jobs, supplementing their day jobs and offering a weekend alternative to bars or movies for just a couple hundred bucks. And if paying a stranger to come to your house and play make-believe sounds odd, take it from Dimension 20’s Brennan Lee Mulligan, who explains why this is such a cost-effective night out:
When people hear the idea of paying a [DM], they have to bear in mind the idea of “how much does it cost to take you and five friends to the movies?” […] It’s like 20-25 bucks for a movie ticket, popcorn’s like 13 bucks—suddenly it’s like $200 [for everyone] to go to the movies. And the Uber there? Forget it. And that’s for two hours.
Think about if you went to the movies and the person making the movie knew your name and was spending their whole week being like “I wonder how I can make this person and their character happy? How can I give them the story their looking for?”
So in the grand scheme of things, it’s this incredibly affordable expense to get this tailor-made experience. For me, the moments I’ve had role playing surpass the moments I’ve had in any other kind of medium […] in terms of the emotional resonance and the catharsis provided by having these stories and telling them with people.
…I mean, custom-made epic storytelling? Pretty cool bang for your buck.
Economics and recreation aside, D&D is even proving to be a niche therapeutic tool. Johns Hopkins psychologist William Nation has developed a D&D-centered therapy group, which combines fantasy role playing with traditional therapeutic techniques. The practice, he explains, creates a “psychological distance” between patients and what they are trying to process, making their emotional issues more accessible and easier to overcome.
So all of this success—economically, socially, and emotionally—is clearly driven by more than just that weird kid from high school who never left his basement. It’s driven by the 50 million players worldwide who have made a character sheet since the game’s inception in 1974.
But why?
Because D&D, in my oh-so-humble opinion, is the ultimate art form. It is an unmatched blend of writing, acting, improvisation, and even set or costume design, all of which transcends any single genre across science fiction, fantasy, comedy, drama, satire, mystery, or romance in a single two-hour session. And the best part? It’s impossible to tell the same story twice. Much like an improv show or a baseball game, even if you started with the same setting and players, chaos theory can dictate a completely different ending to your story no matter how rigid you try to make the game. So aspiring Type-A DMs beware: D&D is a roiling, wily, unpredictable ride that is rarely influenced as much by your meticulous planning as it is by what mood your friends show up in.
My own relationship to D&D has evolved dramatically over my adult life.
The first session I truly remember (because my friend and longtime-DM insists we’d played many times before) was on my 18th birthday. We were camping in southern California, where my parents were graciously hosting a big caravan of family and friends. After a long day of parentally-supervised underage drinking, once everyone else had gone to sleep, my friend busted out eight pieces of paper that would change my life: pre-made character sheets. We picked at random and began our drunken journey. The quest was simple—to escape a literal dungeon—but it involved so many dumb shenanigans, beers, and possibly a celebratory joint that it’s stuck with me ever since. It is a miracle that no one woke up to catch us in the act of being absolute dorks.
Fast forward to the pandemic. Everyone is stuck at home and figuring out Zoom. Most people used it for classes, work, or virtual dates. But the secret use-case that no doubt helped propel Zoom to new heights? Dungeons & Dragons.
Whether I was living at home, “studying abroad” in Colorado for a semester, or returning to awkwardly-hybrid campus life, D&D was there. Once a week, those same friends and I would join a call from all across the country to embark on some imaginary adventure. We fought each other, saved each other, solved puzzles and completed quests, all while talking lots of shit and cracking lots of jokes, before updating our stats and returning to our normal, un-magical lives. Without D&D, I’m not sure we all would have stayed as close—at least not during a very long stretch of some very difficult years.
Fast forward again to my first year living alone. Not under the duress of a pandemic, but by choice: I had just moved to DC with little to no friends and was living in a studio apartment. By then, life was semi-normal again, and there was less enthusiasm among the group for spending one night a week on Zoom.
Then I found professional D&D. A few TikTok likes quickly turned into a monthly paid subscription to Dropout, the popular streaming platform behind Dimension 20. Since it combined audio storytelling with live-action performance, I could listen to it in the background or watch with my full attention. And believe me—I did a lot of both. Doing the dishes? D&D. Long drive? D&D. Friends bailed on Friday night plans? D&D.
I did the math. Since the summer of 2023, I have streamed 291 hours of D&D. That’s more than 12 days. It remains one of my most beloved and reliable content mediums.
But this, of course, does not account for how many hours I’ve spent actually playing the game. And those hours have impacted me in ways I never expected.
If it’s not obvious by my preference for sending faceless messages to friends and family via Substack, I am no stage performer. I have always felt more at home hidden behind a screen, with the time and space to create my best work, than under the literal spotlight of a play. I am a complete coward, which makes me a proud writer.
So one of the things I love most about tabletop RPGs is the chance to perform without a crowd. There’s no audience of strangers—just your friends. But the dynamic is the same: you get to express yourself creatively and spontaneously in the hopes of earning a laugh, gasp, or tear from the people immediately around you. For me, D&D feels unconstrained by the regimented work of writing alone in my bedroom. It’s freer and more dynamic. It’s a chance to play.
For example, I was terrified of doing improv or theater in high school, despite the even worse FOMO of watching my friends do it without me. But in the privacy of a Zoom call or living room? I’m basically Dana Carvey.
I am not alone. D&D’s impact is widespread, and I cannot express how good that is for the world. It is a powerful, underrated engine of socialization and creativity at a time when our politics, technology, and economic woes make us feel like we are desperately lacking it. It’s a safe space to build confidence and community.
Political scientist Robert Putnam—perhaps my alma mater’s most famous alum—is most well-known for his seminal essay Bowling Alone (yeah, that’s how famous my college is). In it, he tracks the collapse of American institutions that once anchored community life and undergirded a strong democracy: PTAs, union halls, Rotary clubs, bowling leagues. Today, we often refer to these as “third places:” physical locations or organizations that are not 1) our home or 2) our work. The few third places that remain usually come with a cost, be it financial or social. Gyms require expensive memberships; bars coerce drinking; even parks are disproportionately concentrated in wealthier areas. The result is an increasingly lonely, fragile, distrustful, screen-addicted, and spiritually-bankrupt society.
Maybe sitting down to play make-believe every once in a while is the solution.
Or maybe it’s not. I understand D&D isn’t for everyone. I just know it could be. It is the most welcoming, disarming community I have ever been a part of. It does not judge, it does not exclude, and it does not cost money.
Most importantly, it’s just fun. D&D is more immersive than any movie, show, or video game. Think of your favorite fictional character: Harry Potter, Legolas, Obi-Wan Kenobi, whoever. Now imagine that, rather than watching that character, you get to be that character. You get to decide what they do and how they act. You get to fight Voldemort, cast the ring into Mordor, or Jedi-mind trick stormtroopers yourself. You get to control the story (dice willing).
And if you’re still hung up on the silliness of the “dungeons” and “dragons” part, I get it. I still call it D&D to strangers because somehow that seems cooler and less dorky than its full name. But just consider this:
In my last campaign, I played a silver spoon trust fund baby who planned to inherit his father’s massive empire once he got a little “real world experience.” So he set out and traveled the world with a newfound a group of friends. He quickly realized he wasn’t that bright (low Intelligence and Wisdom) but had a knack for talking himself out of bad situations (high Charisma). What he didn’t know was his father had actually sent him on this adventure to keep him out of the way—because he always saw him for what his most obvious flaws suggested: an idiot. When my character eventually returned home expecting a hero’s welcome, he found only rejection, and had to confront his father and the ugly reality of his family life. So he did what any lovable idiot might do: he spontaneously robbed his father blind and fled, only to be hunted down by the law and his own family’s paid assassin.
Was it sci-fi? Fantasy? A modern drama? Doesn’t matter. It was a great story no matter the aesthetic, improvised line by line, roll by roll, over countless joyful hours with my best friends.
When I played that character, the pandemic didn’t exist. Neither did the job I was too scared to admit I hated. For just a few hours every Sunday evening, all that existed was a world of portals and pirates and political intrigue, and somehow it felt more real than real life. Every Nat-20 was a triumph; every Nat-1, a tragedy. It was stress without stakes, relief without effort, the full emotional arc of another life without ever leaving my room. It was an escape that allowed me to play as a smarter, funnier, more courageous version of myself with friends who saw me that way even after the session ended.
As Deborah Ann Woll says later in that wonderful, wholesome interview with Jon Bernthal:
[D&D] is the greatest game ever created. It’s just collaborative storytelling.
It’s as close as you can get to when you were seven on the playground just making up games and stories. And I love it.
Laugh all you want at my dungeons and my dragons. But if there isn’t some little part of you that longs for the playground again, for the innocence and whimsy that came before all the work and mistakes of “adult” life, then I’ll be the one laughing—dice and character sheet in hand.
Be well,
Ollie
P.S.
Here’s a mimic and here’s a kobold.
D&D isn’t the only antidote to the ills of our lonely, atomized society. From book clubs to run clubs, there are plenty of ways to find your niche. What’s yours?
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Loved this, and I 100% agree. dnd has been SO good for me and my wellbeing, and it's such an immersive creative outlet that is currently taking up most of my life - and I absolutely love it. Having grown up reading fantasy and playing games like Skyrim and World of Warcraft, getting to finally just BE the character fully is what I have always wanted. And we have so much fun engaging in this with our friends!
Haha, this was great. I’ve known about D&D since I was a kid. I’m 52 so I’m talking about all the way back to the beginnings in the late 70’s, early 80’s. I’ve never been more interested in playing than I am now after reading your essay. Kudos.