Inside the Biggest Live Game of ‘Dungeons & Dragons’ Ever Played

It’s a frosty January night in New York City, but Madison Square Garden is red hot. You feel the heat when pillars of flame spit out from black butane tanks that encircle a half-domed stage. The thunder of swag rock is drowned out by the dog-whistle cheers of 20,000 people alive with electricity. Under the tiled roof where Knicks and Rangers banners hang, between walls that often echo with Billy Joel and Taylor Swift, an epic game of Dungeons & Dragons played by Dimension 20 is about to get rolling.

An arena spectacle with WWE auras is unusual for Dungeons & Dragons, the famously nerdy tabletop game of fantasy heroics and lucky (or unlucky) rolls of dice. It’s also unusual for Dimension 20, a show where Los Angeles comics play serialized D&D games. It is the flagship show of Dropout (formerly CollegeHumor), a streaming service whose organic brand of comedy and feverish fanbase make it agile against lumbering corporate giants. At the center of Dimension 20 is Brennan Lee Mulligan. His ringmaster’s charisma, chameleonic voices, and occasionally viral socio-anarchist zingers work in concert with his encyclopedic knowledge of Dungeons & Dragons Fifth Edition to qualify him as arguably the greatest Dungeon Master alive. Normally Mulligan’s games are filmed in an L.A. studio, on a domed set that looks like a spaceship’s interior where players sit around a U-shaped table. But tonight they’re inside the Garden, standing where Frazier upset Ali, waving to a roaring crowd on a 360-degree stage illuminated by a pattern of LED triangles under a waterfall of golden stars. Tonight, these jesters are turned into rock stars in the heart of midtown.

Since its launch in 2018, D20 has survived a gauntlet of uncertainty, rocked by layoffs from its corporate owners just before a pandemic sent them all playing virtually in isolation. Now Dimension 20 thrives as one of the most popular tabletop role-playing games (TTRPG) shows on the internet. Their sold-out MSG event, “Gauntlet at the Garden,” slated to premiere on Dropout later this year, affords Dimension 20 bragging rights as the hosts of the single-biggest live game of D&D ever. That’s even bigger than when fellow D&D troupe Critical Role sold out their Wembley Arena show in October 2023. While MSG is a one-night-only affair that D20 just might outperform themselves later this year — they have more live events set for Los Angeles, Seattle, and Las Vegas — a capacity crowd in the “World’s Most Famous Arena” for a tiny streaming show centered around a 51-year-old game is proof that an online audience can and will log off and show up. It is revealing of Dimension 20 itself, an oasis of warmth in an unmagical and increasingly frightening cold world. 

“Everyone understands storytelling on a profound level,” Brennan Lee Mulligan tells Rolling Stone. “Every culture in the world uses it to talk about what matters, to talk about being human. What makes people come back [to watch us], season after season, rests on characters people love and stakes they feel in their spine. They feel the weight of these journeys.”

“Gauntlet at the Garden” is ineffable for what might still seem like a niche hobby, a game still played mostly on kitchen tables. As the music fades and the cast take their seats, the jumbo screens that normally display Knicks scores now sport the blown-up faces of Dimension 20. Surrounding the headliners are grumpy arena security, who spend the night wearing baffled expressions watching a sea of adults cheer and laugh and applaud over imaginary characters engaged in battles no one can actually see, and rolls of acrylic dice just 16 millimeters in size. D&D is a game of the imagination, but with the right pieces, the allure for stories that unfold with total spontaneity is no fiction.

With his castmates before him, Mulligan, a 37-year-old improv performer with bouncy theater kid energy, ginger-red hair, and an AM radio DJ’s voice, greets his hometown of New York City. “Hello, one and all!” he booms, ringing through arena speakers like the voice of God. 

Actually, playing God is kind of Mulligan’s deal on Dimension 20. He is its resident Dungeon Master, or DM. It’s a complex task requiring many hats at once: story writer and narrator writer, rules referee, ensemble actor. (Mulligan is a virtuoso of impressions, with midwestern dads and drunk bachelorettes a few personas he’s adopted as DM.) DMs, like Mulligan, kick off games of D&D by verbally describing the story — who, what, why? — before painting more vivid descriptions of the worlds the characters exist. The players, in turn, describe their actions and converse in-character, and so it can go for hours, even days, across campaigns that can last years. That’s the cadence of D&D, and to watch others engaged in it is akin to watching actors at a table-read, except without a script.

“On a primal level, I’m asking: What’s going to make my friends happy?” Mulligan says. “Telling stories with friends is perennial. It refreshes itself because people are refreshing themselves.”

To be a good DM is to have a third eye for creativity. It’s not just describing worlds that aren’t real with the clarity of a dispatched reporter. It’s bringing to life characters born in that instant. It’s unspooling lore and unraveling plot twists with little preparation. “Gauntlet” had rehearsals for lighting and music, but no one knows how the story will end. Not even Mulligan. “There is no way to practice,” he says. “You can do lots of planning, but you cannot practice. Nothing recreates the environment of being there, in that room, with that audience, until you are there.”

Around Mulligan are the “Intrepid Heroes,” D20‘s stars from the L.A. comedy scene. There’s Lou Wilson, a teddy bear of a man who announces for Jimmy Kimmel Live; Siobhan Thompson, a peppy Brit with cat eye glasses and a blonde bob with writing credits on Rick and Morty; Zac Oyama, a soft-spoken soul whose sharp cheeks house a boy band smile; Ally Beardsley, a nonbinary individual with a cropped mullet and a skateboarder’s zen; Emily Axford, a New York native with undertones of Bettie Page and Tina Fey; and Brian Murphy, an ex-MTV host with horn-rimmed glasses and gelled hair whose habit of bad dice rolls can be appropriately called Murphy’s Law. (Axford and Murphy are married, and played versions of themselves on Adam Ruins Everything on truTV.)

After a roll call where each reveals their imminent reprisal of fan-favorite Dimension 20 characters — including a Staten Island divorcee, a wisecracking pizza rat, and a drug dealer still coping from a breakup  — the game begins. With painterly narration, Mulligan whisks the audience (mentally) back to The Unsleeping City, a story first explored in 2019. It is an urban fantasy, a glittering New York like the one just outside on Seventh Avenue. But in Mulligan’s vision, a secret parallel world is teeming between the cracks of concrete.

“We go to other worlds not to escape, but to imagine what this world could be and should be,” Mulligan tells me later. “We tell stories about heroes to understand how to become them. We’re looking at frightening times. My goal with Dimension 20 is to make the best show I can. If I thought stories did not motivate action, I would stop telling them.”

DIMENSION 20, SO NAMED FOR its multiversal anthology format and the twenty-sided die of D&D, is a leader in “actual plays,” also called live plays, where people play Dungeons & Dragons for an audience. Other prolific actual plays like Critical Role, Acquisitions Incorporated, and The Adventure Zone star voice actors or comedians — professions suited to D&D‘s role-playing. Dimension 20 seizes on the synergy, what Mulligan says is “such a clear marriage” of improv comedy and fantasy. “It is something that seems so clear in hindsight, but has become a surprise in this boom of actual plays,” he says.

Dungeons & Dragons was created in 1974 by midwestern gaming legends Gary Gygax and Dave Arneson. Players adopt alter egos, from warriors to sorcerers, who traverse worlds of mysticism and monsters. The outcomes of challenges, like slicing orcs with axes or smooth-talking tavern maidens, are decided by dice. The higher the rolls, the better the result. Twenty is the highest possible number, and to roll it naturally (a “natural 20”) is a soaring success. Roll a one, however, and that is a critical failure. Whatever players do, it’s up to the DM to reinforce the guardrails and impose stakes, building suspense, exerting godlike control while yielding to the power of chance created by players. Such is the joyous tension of the game.

“The game is the tool. Story is the most important part,” says Thompson. “Sometimes failing and losing is more interesting than succeeding.” At MSG, Thompson reprises her role as Misty Moore, a Broadway diva prone to calling strangers “dah-ling.” In fan art, Misty is often illustrated in color palettes of glamorous gold and white. As a Bard (her character class) Misty casts magical spells through singing — and at Level 12, she’s very good at it. 

Zac Oyama, who role-plays a himbo firefighter named Ricky Matsui, says he considers it “kind of a gift” that D&D allows their improv training to shine. “It lets you know what you’re supposed to do,” he says. “If you jump across a skyscraper, you roll one and fall, it’s funny. You embrace that. Rolling in the middle is boring.”

It’s surreal to see the golden age of actual plays when you know the baggage that used to follow D&D. In the 1980s the game was engulfed in the Satanic panic, attracting accusations of perverting youth with witchcraft. In 1982, a young Tom Hanks starred in Mazes & Monsters, a made-for-TV movie about a deluded college student who becomes dangerously obsessed with D&D. In the climax he nearly leaps off the Twin Towers, believing it to be a gateway to a magical realm. While this notoriety is a key chapter in the game’s cultural mythos, today, D&D is valued intellectual property owned by Hasbro. 

The stars aligned for actual plays to rise in the 2010s, owed to a zeitgeist where geek became chic. The success of the Lord of the Rings and Harry Potter films were the overture for Game of Thrones to become a smash HBO show, to say nothing of the books that spawned them. Meanwhile, a generation of Hollywood writers with fond memories of D&D featured it in shows like Community and Stranger Things. During Covid-19, Dungeons & Dragons saw a prodigious surge in interest as isolated friends reconnected by playing the game remotely, which is possible over online platforms like Roll20 and communication tools like Discord.

Actual plays also found a sizable audience in 2020. For Dimension 20, its existing library of pre-pandemic games attracted people who maybe craved togetherness and lighthearted escapism. “I’ve heard from people that during those lonely times, we were there to keep you company,” says Beardsley. In the green room of MSG before the show, Beardsley says the live events Dimension 20 is embarking on “is completely about people fighting back against isolation.” “Covid pushed us into a deep loneliness being separated from people,” they say. “This is a moment that could never have happened during that time.”

“Stories like this help people make sense of uncertainty,” says Oyama. “Where you don’t know how you’re gonna get out of situations, it’s nice to see the bond of this group. How we can rely on each other and push through anything.”

In the actual play scene, Critical Role keeps a high profile with institutional footing. The show, which airs as an internet livestream, features cartoon voice actors led by their DM, Matthew Mercer. Since its premiere on Twitch in 2015, Critical Role now boasts 3.78 million subscribers across Twitch and YouTube, mountains of merch, and a Prime Video animated series. For comparison, Dimension 20‘s YouTube channel has just 997,000 subscribers. (Dropout, their primary streaming platform, does not disclose viewership numbers.) 

But Dimension 20 is no underdog. It is a major endeavor by Dropout, the comedy streamer sprung from defunct website CollegeHumor and has a cult subscriber base. D20 is defined in the space by its unique brand of feel-good antics and top-shelf production. Where most shows simply stick a camera on a tripod, Dimension 20 lends immersion as its moving camera weaves over arrays of painted miniatures. Inch-high avatars stand to scale in lush 3D sets of magical forests, hellish underworlds, even high schools. Cinematic sound mixing, from the glimmering metal of swords to the rumble of grenades, add texture to Mulligan’s phlegmy mouth effects. 

“The amount of artistry Dimension 20 has behind its scenes to show the world of our imagination have set us apart,” Mulligan says. “The editors, the people that design the miniatures, the list goes on. I cannot articulate the pride I feel. The people we are competing against are none of our fellow shows. We’re competing against ourselves, from the last season.”

Dimension 20 tells stories that detour from the known roads of Tolkienesque fantasy. Rather, a D20 campaign might look like a John Hughes drama (Fantasy High), or a mishmash of 1980s and 1990s action movies (Never Stop Blowing Up), or a bizarre concoction of Game of Thrones with Candyland (A Crown of Candy). Dungeons & Drag Queens is an increasingly popular sub-series under Dimension 20 where a bedazzled Mulligan holds court over RuPaul’s Drag Race alumni. If you’re sick of dungeons with dragons in them, Dimension 20‘s laugh-out-loud campaigns are a panacea.

The show came to life in 2018, when comedy website CollegeHumor launched Dropout as a streaming service to platform more ambitious content than their output of digestible sketches on YouTube. Mulligan, a staff writer and performer at CollegeHumor, was invited by then-Chief Creative Officer Sam Reich to adapt his home games of Dungeons & Dragons for a show in the vein of Critical Role. Most of the cast assembled were already CollegeHumor colleagues. “It felt like a no-brainer,” remembers Thompson, adding Lou Wilson came from another game run by Mulligan. Beardsley was a “last-minute” replacement for comedian Rekha Shankar, who joined CollegeHumor in 2017 and is now a regular on other Dropout shows like Game Changer. (Shankar has since played in various seasons of Dimension 20.) “Ally has put a huge stamp on the show,” comments Thompson. “I don’t know what the show would look like without Ally.”

Mulligan knew from the second episode they were on a different level than their competitors. Stepping into the domed set for the first time was one thing, but “watching players grab their miniatures” based on their characters was another. The engrossing camerawork by cinematographer Kevin Stiller, who plunged eye-level to a battle inside a high school cafeteria, gave Dimension 20, well, dimension, according to Mulligan. “When you see the jib arm moving through the space, we were bringing something to the potluck that’s not there already,” he says.  

“When Dimension 20 began, our goal posts were, ‘Let’s be the funniest TTRPG show,’” says Sam Reich, who was made CEO of CollegeHumor in 2020. Reich echoes Mulligan, believing episode two was when he knew it had sauce. “It shocked me to attention,” he says. “I got the same laughs I get watching comedy, the same sense of immersion I get reading a novel. A byproduct of comedy is that it lowers audience defenses. When defenses are down, you’re more susceptible to emotionally resonant storytelling. Between those spaces are where you can hook people.”

DURING THE MSG SHOW, the audience is invited to roll along a few times. A QR code will pull up virtual dice, and the most common number rolled by the audience is displayed in jumbotron-sized glory. This happens early on in the night when the multiverse ruptures to allow two characters from other campaigns to cameo. It’s a crowd-interactive “Choose Your Own Adventure,” with Mulligan’s agility as DM to move with it. After two bummer rolls, a benevolent Mulligan gives the crowd “advantage” on another — a stipulation that allows two rolls of a 20-sided die instead of one. There’s a pause, and then it’s there, blown up for all to see: “20,” in glowing gold over an onyx die. The audience comes unglued, drowning out Mulligan’s introduction of cult favorite characters “Plug Strutt” and “Ayda Aguefort,” who enter through the rift. Once again, there is nothing to actually see, but such is the spellbinding power of a good story.

Later in the night, the heroes stand against a “business dragon” named Kalvaxus who’s taken over Wall Street. Mulligan invites Thompson — after her Misty used magic to compel the dragon to dance as a distraction — to roll for the dragon’s power to resist it. (This is a rare case where a low roll is desired.) Mulligan hands Thompson a comically oversized 20-sided die, a boulder in Thompson’s petite arms. As he explains the stipulations of the roll to the audience Thompson runs up to fans in the front row, inviting them to “bless the die.” 

It is the final roll of the night, lest the audience want a reroll. “Just start chanting reroll,” Mulligan calmly explains to a buzzing crowd. Thompson rolls a 19. The crowd boos before chanting for the reroll. Will the dragon dance because of a powerful Broadway superstar? Or will the center of the universe succumb to a snarling, fire-breathing beast? At last, Thompson rolls, and — well, that’s a spoiler. 

There lies what might be the real spell of Dimension 20. Sure, the miniatures and the pyrotechnics are neat. And yes, the talent of the stars, their magnetism and comic timing are a draw. But it’s the moments of hushed suspense, when the die is cast and no one can predict what will happen. That’s been the story of Dimension 20, too. It’s an unlikely thing, where the pieces and the elements come together to create something that still defies words. One might call it magic. 

From Rolling Stone US.