When CollegeHumor launched Dropout, it felt like a genuine surprise. As Sam Reich joked at the time, “It’s like Netflix, but cheaper.”
One of the standout shows on the service was Dimension 20. Each season features a group of comedians playing Dungeons & Dragons, with a new setting and cast of characters. The first season, Fantasy High, quickly gained a devoted following. Since then, live shows and side quests have expanded the universe, introducing new characters and stories.
The Unsleeping City marked a return of the Fantasy High cast in a brand-new campaign—this time set in modern-day New York City. From the very first episode, it was clear this season was doing something different.
Dimension 20 Is Fun to Watch
The premise of Dimension 20 makes two things immediately obvious:
- The cast and producers genuinely love what they’re making.
- They care deeply about the audience watching it.
Watching people inhabit D&D characters around a table—fully committing to the bit, the drama, and the emotion—can feel strangely profound. Episodes often run close to two hours, but they pass effortlessly. You sit down thinking you’ll watch “just a bit,” and suddenly the episode is over.
Even shorter seasons and side quests feel intentional rather than disposable. They give the main campaigns room to breathe while still delivering memorable stories.
More “Produced with Love,” Please
What I appreciate most about Dropout—and Dimension 20 in particular—is that it feels made because someone wanted it to exist.
There’s a sincerity to it. Not slickness. Not corporate obligation. Just people making the kind of shows they’d want to watch themselves.
I like to think of it as produced with love. It’s not about budget, acting pedigree, or production tricks. It’s about intention.
Dropout has other great examples of this approach. One of them is Troopers, a short parody series set in a Star Wars–inspired universe. It’s funny, tightly written, and clearly made by people who love the genre they’re poking fun at. That kind of project feels rare outside of places like YouTube—and it fits Dropout perfectly.
The Unsleeping City Is Set in New York
I love New York City. I’ve visited a few times over the years, and seeing it reimagined as the setting for a D&D campaign feels like visiting it all over again.
The city is blanketed in snow as Christmas approaches. Brennan Lee Mulligan’s affection for New York is obvious in the way he describes it—not just as a backdrop, but as a living place filled with small details and personal history.
There’s a difference between imagining a fantasy city on the Sword Coast and playing in a version of NYC you’ve actually walked through. One feels like invention. The other feels like memory.
At one point, the story features an empty Times Square. Take a moment and really sit with that image. It’s strange, powerful, and oddly terrifying.
And the city is only part of what makes the season work.
The Characters Are Interesting and Diverse
The characters in The Unsleeping City feel like reflections of the city itself.
Pete is a transgender man navigating magic, identity, and daily life in New York.
Sofia is a monk hairstylist whose personal history gives some early jokes an unexpected emotional weight.
Kugrash is a rat druid devoted to caring for people society often ignores.
Ricky is a firefighter paladin—a good-hearted jock struggling with self-image.
Misty Moore is a Broadway star bard, theatrical and mysterious in equal measure.
And Kingston is the quiet center of it all, a healer who looks after both magical and very human needs, often putting others before himself.
Together, they create something special. You don’t just want to see what happens next—you want to see what they become.
We Should Support More Shows Like This
Content like Dimension 20 reminds me why I love watching tabletop RPGs in the first place. It’s creative, collaborative, and deeply human.
I don’t want shows that feel like marketing vehicles or corporate obligations. I want stories made because someone cared enough to tell them.
The Unsleeping City delivers exactly that.
Years later, with many seasons now behind it, it still feels like one of the most personal things Dimension 20 has ever made—and I’m glad it exists.
