These 7 comedians built a business playing ‘Dungeons & Dragons.’ Now they’re taking that magic to Madison Square Garden.

And Mulligan’s now nerdworld famous, not only for being one of the creative minds behind the Dropout business engine. Months from now, Mulligan and his team at “Dimension 20” will do what no “Dungeons & Dragons” roleplaying game crew has ever done to date: take their show to a sold-out, one-night-only gig at Madison Square Garden.

The geek business is booming, evidenced by the collective success of “Dimension 20” and Critical Role, a gaming business co-founded by a team of eight voice actors.

Critical Role in October held a sold-out show at the Wembley Arena in London, then followed it up in June with another live gig at the Greek in Los Angeles. So with the popularity of “Dimension 20” — the program that keeps the streaming platform Dropout going — and Critical Role’s spinoff ventures in podcasting, animation, and new games, it’s safe to say that it pays to be a geek.

Enter the intrepid heroes

There was a time, however, when the idea of recording yourself playing “Dungeons & Dragons” was a tough sell.

In 2018, Mulligan pitched the idea to his then-CollegeHumor team to film a group of his friends playing “Dungeons & Dragons.” It was a daring gambit for a young actor who’d mostly become internet-famous for playing unhinged CEOs melting down in interviews.

When the idea was greenlighted, Mulligan gathered a crew of six other comedians — Emily Axford, Ally Beardsley, Zac Oyama, Brian Murphy, Siobhan Thompson, and Lou Wilson. Together, they debuted “Dimension 20’s” first season, “Fantasy High,” a 17-episode series set in a high school where the kids slay monsters. Mulligan took on the role of dungeon master, guiding the narrative and playing all the non-player characters that “Dimension 20’s” group of “intrepid heroes” meets.

“Dimension 20” is shot in a dome, with special effects and projections. Its campaigns are also shorter than those of other stream-based “D&D” shows like Critical Role, which consistently runs campaigns with more than 100 episodes. Some “CR” episodes can run for six hours, but “Dimension 20” episodes tend to be around two hours long, topping out at three.

Fast-forward to 2024, when “Dimension 20” is coming off a sold-out tour of live shows in the UK. Months from now, the crew will be heading to Madison Square Garden on January 24 for their “Gauntlet at The Garden” live show, continuing where they last left off with their “Unsleeping City” campaign.

“We’re going to come out where the Knicks play, and we’re going to play ‘Dungeons and Dragons,'” Mulligan said. “It’s silly, it’s amazing, it’s beautiful, and it’s all dedicated to the hard work of all of our amazing cast and crew.”

Oyama told Business Insider that the idea of playing “D&D” live in an arena of nearly 20,000 people still hasn’t fully sunk in. But he says it’s definitively “surpassed any benchmark” of what he thought “Dimension 20” could do.

In the “Unsleeping City,” Oyama plays Ricky Matsui — a New York firefighter with paladin powers. And now, he’s trying to figure out what “version of Ricky” to bring to the stage.

“I’m not sure what Ricky we’re going to get. Is it a little bit further back, or is it in the future? We’ll see,” Oyama said.

The rise of Dropout

Dropout was no overnight success.

For one, 2020 saw an almost complete wipeout of over 100 staff members at CollegeHumor. Sam Reich — now CEO of Dropout — decided to buy the company and start rebuilding it.

“It was a tragedy, like a hundred of the best and brightest people I had ever worked with were suddenly let go,” Mulligan said.

Mulligan was one of the seven people left on staff and the only creative. Then COVID hit, and they had to figure things out again. “Dimension 20” and Reich’s “Game Changer” were the main pillars of the company’s content.

“It felt like that scene in ‘Howl’s Moving Castle’ where the whole castle falls apart, and it’s just the two little legs running around,” Mulligan said. “Now Dropout is as vibrant and alive as it’s ever been.”

Dropout has managed to keep the streaming machine humming. Reich told BI that the subscriber count stands in the mid-high six figures, with 65% of its subscribers coming from the US. Subscriptions start at $5.99 monthly and $59.99 annually.

“Near-term, we’re hoping to take advantage of what we know about our audience, as well as our in-house development process, to produce more shows in our sweet spot: unscripted and in the studio,” Reich said. “Longer-term, we hope to put other formats back into the mix.”

Notably, in 2023, the company did well enough to share its revenue with its creative staff and said it planned to double the number of programs on its platform — though Mulligan’s “Dimension 20” remains one of its major draws.

Anti-capitalism and found family — with dragons

One thing that’s remained consistent with the more than 20 campaigns “Dimension 20” has run is Mulligan’s motivation to highlight real problems in the world through comedy and fantasy role-playing.

In the “Unsleeping City,” for instance, an angelic embodiment of the American dream is corrupted, and in “Fantasy High,” the students have to fight a libertarian dragon.

Mulligan says his team at Dropout has also found a way to do some good. The miniatures from their “Dungeons & Dragons” games were “collecting dust,” he said, and it was “heartbreaking” to throw them out, so they auctioned them off to raise funds for the Palestine Children’s Relief Fund.

“If I’m telling stories for a living, it occurs to me that I should make them be about the things that matter in my estimation. And if we’re telling stories about adventure and heroism, why wouldn’t I select what I see as the great dragon, the ogre of the age in which I find myself?” he said. “The Brennan Lee Mulligan of a couple hundred years ago might’ve been talking about a different thing, but the one who’s alive in 2024 has it got to be talking about capitalism.”

Oyama, meanwhile, told BI that the concept of found family has always been meaningful to him.

“I think being able to connect with folks in that realm and realize that although you’re the family you are born into is one that you can love and care about, there are similar structures out there that are just as meaningful if you don’t have that,” he added.

A love letter to New York

Mulligan told BI he’s still in a state of “bewildered gratitude” that a kid from New York would one day find a way to bring “Dungeons & Dragons” to Madison Square Garden, close to where he used to work.

Mulligan is also looking forward to paying homage to New York, which he calls “the greatest and best city in the world,” one that he saw a lot of with his father.

“We would travel all over the city up and down, and my dad would constantly impart stories about the history of New York. And his love for that city is very reflected in every chapter of ‘Unsleeping City,'” Mulligan told me.

He’s also raring to revisit the plotlines in “The Unsleeping City,” where “Dimension 20’s” games last left off.

“I think there are going to be some pretty huge twists,” Mulligan said. “There are a couple of little tricks up my sleeve that I don’t feel I can spoil here, but I can say people should get ready for a surprise.”

Fans of “Dimension 20” can also expect more content featuring its cast of seven intrepid heroes.

“I have multiple text messages from the Intrepid Heroes on my iMessage account, like, ‘I can’t stop thinking about the next season. I have four character ideas I want to pitch,'” Mulligan said. “This is going to be so much fun.”