The best entertainment of 2023: The brilliant storytelling of Dimension 20

Through a long year, this podcast/ video show was my constant and delightful companion

No cultural offering this year has brought me more consistent joy, entertainment and comfort than Dimension 20. Frankly, I don’t even remember Barbie or Oppenheimer, not that we should be pitting strong cultural artefacts against each other. Toxic behavior.

None of what Dimension 20 does is easy - and in a somewhat crowded field of D&D style podcasts and video shows like Critical Role and The Adventure Zone and Dungeons and Daddies, it’s not easy to make shows that feel new and exciting and elevated. But they do it.

If you’re not familiar, Dimension 20 is tabletop role playing game show produced by Dropout (who also have a bunch of other great stuff, like the Game Changer show). It usually uses classic roleplaying game Dungeons and Dragons as the core mechanic for its various seasons, and stars amazing improvisers, actors and comedians. Also sometimes drag queens, but more on that later.

The cast of Fantasy High, aka the intrepid heroes

There are a couple of different dungeon masters who create and run each story (I’m a big fan of Aabria Iyengar’s calm and quietly sadistic storytelling, I really enjoyed her Burrow’s End storyline), but the original DM and creator of the show is the upsettingly brilliant Brennan Lee Mulligan.

Each season uses the D&D rule system as a starting point, but play with fantasy as a genre. You have a fantasy world smooshed with 80s John Hughes films in Fantasy High, an urban fantasy set in the hidden corners of magical New York in The Unsleeping City (my personal favourite series), sci-fi spaceship series, regency romance with fairies series, fantasy film noir mysteries, and on and on. This year, one of the funniest and most joyous seasons of Dimension 20 was Dungeons and Drag Queens, where several queens from Drag Race get introduced to D&D and absolutely slay.

The next D20 season, releasing in January 2024, will be the third installment of their very first story, Fantasy High, which I’m incredibly excited about. It’s one of the more unique fantasy world’s I’ve experienced, the first season following a kind of Breakfast Club style narrative with a dragon trying to eat all the kids.

Not every season is equal - there’s an element of chance to how the storytelling plays out, due to the improvised nature of the game. There’s also something for almost every interest - some are more comedically led, others more consistent with fantasy lovers, lots of different genres and styles and tropes. But it’s all done with care and craft and creativity and humour.

This year, the intrepid heroes and pals have been my constant companions. I watch and listen to these shows on the Dropout app, switching between YouTube style video watching or audio only, so I can consume it like I would a podcast. They’re in my ears as I spend my weekends baking and cooking, on the tram to new jobs, doing long depression walks down by the river. They’re what me and my friends talk about as we play our own games. They’re what inspired me to start dungeon mastering my own story (although in D&D tradition we’ve only managed to coordinate two sessions).

The thing about Dimension 20’s stories is that it’s the perfect storm for me. I’m a massive fantasy reader, I’m deeply immersed in a lot of narrative construction, and I’m an improv comedian. Ladies and gents, line up! I would say my love of improv is at least partially motivated by watching the rules of narrative and comedy play out in the moment (also I love being a silly little man on stage!).

It’s very clear that many of the players in Dimension 20 series are brilliant long form improvisers, with such experience and grasp on the form that their narrative choices and commitment to character seem magical. They deeply engage with both the humorous choices in the show - and it can be very, very funny. There’s a line by Zac Oyama, the context which I won’t spoil ("If we're all sharing secrets, I wasn't always a firefighter."), whose ridiculous dry delivery gets me every time, that made me laugh so much that a goose got disturbed and chased me while I was on my walk near the river.

They all have an easy comedic language that only comes from talented improvisers trusting each other and working together for a long time. There are running gags, character choices, even weird voices that have become a regular part of my lexicon now. As a sometimes comedy writer, if I could craft something as absurdly hilarious as Hilda Hilda, I could die happy.

But they’re also not afraid to engage with real emotion, and genuine narrative stakes. Brennan as a dungeon master is basically writing a novel on the fly each series - I’m not exaggerating. His grasp of both narrative and how to structure an improvised scene is intimidating, and when you add his skill with character voices, his encyclopedic knowledge of D&D rules, and occasional forays into based Marxist theory, you realise that something unique is happening here. He has an iron grasp on how to mix comedy and real emotion, which has informed the majority of Dimension 20’s shows, creating a baseline for narrative stakes that I appreciate. I need my narratives, even when funny, to take their own worlds seriously.

The emotion is manifested usually through strong character choice - I’ve gotten teary from moments where characters have been allowed to explore their interpersonal dynamics, for no immediately recognisable plot benefit other than the deepening of our understanding of who they are. However, because they are improvisers, nothing is ever dropped - in improv, anything that comes up is held aside to be used later. This is particularly meaningful when it interacts with chance. D&D is based on the luck of the roll, with dice being the primary way that characters interact with the world. In A Crown of Candy, a ridiculously good Game of Thrones style fantasy world populated by confectionary, there are a couple of brutal moments where dice rolls go bad, and characters are given tragic deaths as a result. This would mean nothing, even with the rush of bad dice luck, if there wasn’t such a commitment to the internal stakes of character building.

@dimension20Possibly the greatest moment in Dimension 20 history? #dimension20 #acrownofcandy #dnd #funny #rpg #dndmeme #fyp

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Part of this commitment to character comes through the quietly fervent commitment to queerness that the show has. We’re not just talking representation or whatever - we see sexuality and gender explored and roleplayed in beautiful and meaningful ways. As someone who first engaged with my sexuality through a roleplaying game in my teens - I spent several years roleplaying a drunk bisexual elf, only to become a drunk bisexual elf in my twenties - I know how important and meaningful this can be. We call it manifestation these days.

One of their seasons this year was the aforementioned Dungeons and Drag Queens, another way that Dimension 20 proves that they are making content specifically for my interests. The Dungeons and Drag Queens episodes dropped during some of the most heated attacks on the LGBTIQA+ community in the United States, with a particular attention on banning drag queens. It’s a solid way of supporting our community, and also being ridiculously funny. It’s why the bigots will lose, in the end.

I hate being one of those people who wax lyrical about the power of stories - always makes me feel like I’m being lectured by a librarian who smells like mildew. But in a world where creative risks are being limited by the cruelties of late capitalism, Dimension 20 feels fresh and inclusive and joyful. I’m deeply excited about a new year of silly, heartbreaking, nonsense stories.

Also, as I grapple with my place in a broken media industry in Australia, as we see streaming services devalue and cancel the art they platform, the success and kindness of Dropout in general does give me a smidgeon of hope that there’s still a place that values creativity and comedy and writing (hire me lol).

Anyway - if I’ve convinced you, I recommend starting with season 1 of Fantasy High, and you might even sync up with the new season in January.

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