Note: Special Exhibition is a biweekly series I’m doing at Nutgraf, where we pick a single creative project at random to review every week. You get my unfiltered thoughts, personal opinion, and critique on everything from TV shows to magazine issues to Fortune 500 marketing campaigns. There are no rules when it comes to format, genre, industry, or tone. If you have requests for an IP you’d like to see critiqued, drop me a line at ritoban@nutgraf.press.

Are you a fan of Star Wars, Game of Thrones, or Indiana Jones? Do you like Dungeons and Dragons? 

If you answered yes to both but think those things have got absolutely nothing to do with each other, allow me to introduce you to something crazy. Dropout.TV, a comedy-focused streaming platform that costs less than $7/month, is currently rolling out the 26th season of Dimension 20. 

It’s a live-action roleplaying game featuring comedians and actors who play D&D campaigns inspired by fan-favorite pop culture worlds. So far they’ve done high fantasy teen drama, Bridgerton-inspired Victorian romance, a whacky political fantasy that’s a cross between Sausage Party and Game of Thrones, plus a whole lot more. 

Each season is a joyride of its own, but their latest season, a steampunk adventure called “Cloudward, Ho!” might be D20’s magnum opus. I’ve been watching “Cloudward, Ho!” on Dropout since June. Here’s why I think it’s the best thing to happen to the comedy world in a long time, even though it’s much more than just a comedy show.

A crisis of originality

When you struggle with chronic depression from a young age, you learn to look for support tools where you can. And if, like me, you’re insane enough to pair that with a job that requires you to stay abreast of current events no matter how demoralizing they may be – you’re guaranteed to need something soft and warm to fall back on when the feelings hit.

Journalism is my poison of choice. Comedy is the antidote. 

You may find it masochistic that I abandoned any hopes of a medical career to protect myself from the ravages of workplace anxiety, only to dive headfirst into a profession that meant researching and reporting on the hardest issues facing humanity for the rest of my life. “I’d just have to avoid any stress-inducing topics,” I had told myself. Last week, I wrote about school shootings.

My brain seems to have a threshold for how much cynical content it can consume before it begins to edge towards depression. Medication helps, but sometimes you need a pick-me-up. 

Luckily, I learned a trick. By paying close attention and timing it just right, I’ve learned to alternate between depressing real-world content with just the right amount of funny and hopeful shit. Whimsical children’s fiction. Heartwarming sitcoms. And a ton of comedy shows: stand up, improv, satire, song parodies. Pretty much every genre of comedy under the sun.

That said, it isn’t an easy find. Most comedy today feels rote. It’s too safe, too predictable, too uninspired. But there are exceptions. 

Comedic roleplaying redefines improv

Tabletop RPGs aren’t something you’d typically associate with comedy. If anything, most roleplaying enthusiasts seem to take their characters too seriously. It’s not that I don’t respect that. 

But as anyone who’s actually played a session of Dungeons and Dragons with close friends knows, things can get out of hand pretty quickly. Players keep wanting to try crazy hijinks. Things that border on throwing the rulebook out of the window almost entirely. Plus the insane dicerolls sometimes are on their side. 

Eventually, every fun tabletop gaming session reaches a point of chaos that stretches credulity, which makes for the hilarious moments that make playing with friends so special in the first place. Game masters try to work around this stuff, using rules and penalties to keep players in line. But not Dimension 20.

If you aren’t familiar, Dimension 20 is the D&D actual play show from the cast at Dropout, previously known as CollegeHumor. Just to give you an idea of how madly popular this show is, their most recent live performance at Madison Square Garden attracted over 20,000 fans. And that’s not even counting the subscribers on Twitch, YouTube, and Dropout’s own streaming platform.

“Cloudward, Ho!” is the latest season of Dimension 20, featuring a cast of professional improv comedians navigating through a high-stakes D&D campaign inspired by the likes of Twenty Thousand Leagues Under the Sea and Indiana Jones. 

Creativity is over the top this season, with custom minis, battle sets, endless props, and a stage in the shape of a glass dome made of shifting displays that change to reflect the in-game environment the players are navigating at the time. 

Each player is doing accents, acting out scenes, the whole nine yards. You’ll find yourself grinning side to side at the weird character interactions, laugh hard at their many jokes and bits, and learn to appreciate each player as a brilliant comedian in their own right.

I’m just going to say it. This is what comedy should look like in 2025. 

What makes Dimension 20 so cool?

Dimension 20 isn’t the only D&D actual play show around. And it isn’t the first. 

You’ve probably heard of Critical Role, the YouTube actual play channel whose highly successful Vox Machina campaign recently got adapted into an animated series by Amazon Prime Studios. There’s also an entire list of audio-only D&D podcasts on Spotify and YouTube that you can listen to.

But, D20 is the only show I’m aware of that combines an incredible production value with stories with such heart to them. Every season, despite drawing inspiration from various genres and materials, features an original story with deeply humanized characters on journeys at once exciting and emotional. 

(I sobbed hard when Kugrash sacrificed himself at the end of “Unsleeping City.” Kudos to DM Brennan Lee Mulligan for managing to make people care about a human-sized rat who lives in the subway tunnels underneath NYC.) 

And yet, the bits are hilarious and out of control. Without taking away from the immersion, the players manage to weave in funny jokes and scenes like Bert Chapman’s aioli recipes and Gorgug’s “Are you my dad?” moments every time he rolls a low intelligence die.

“Cloudward, Ho!” is the best season so far, hands down. You can tell that the players have really come into their own as expert storytellers. 

While some past seasons suffered when the players weren’t on the same page as the DM, leading to crucial story moments not landing well, this latest campaign is a lot more tightly integrated. My personal favorite as a player is Emily Axford, just ‘cause of how deeply she gets into her characters and tries to empathize with them.

I’m not going to spoil anything from the actual plot. There’s a lot of insane creative shenanigans going on from parallel universes to dinosaur armies to eldritch cults. You should experience it all for yourself. 

But definitely don’t sleep on this. It’s crazy how amazing creative folks can be when they have the leeway to pick their own direction. While streaming networks like Netflix and Amazon Prime continue to suffer from poor management decisions, Dropout’s bold take on modern comedy is a breath of fresh air.