Dropout TV’s tabletop comedy show Dimension 20 just dropped the trailer for their sixth Side Quest, which finished filming last month. Taking place after the events of Fantasy High: Sophomore Year, this adventure is set in the pirate city of Leviathan, aka the Jewel of the Celestine Sea. This Side Quest stars Carlos Luna as Cheese, Krystina Arielle as Barbarella “Bob” Sasparilla Gainglynn, Aabria Iyengar as Myrtle the Bitch, B. Dave Walters as Marcid the Typhoon, Marisha Ray as Sunny Biscotto, Matthew Mercer as Jack Brakkow, and Brennan Lee Mulligan as the returning Dungeon Master.
What do we know about Leviathan?
Leviathan is a pirate city in the Celestine Sea made of shipwrecks that have been strung together to form an island that inhabits roughly 1.5 million people (yikes, that’s a lot of NPCs, good luck Brennan Lee Mulligan). This location has already featured in Dimension 20 LIVE; if you have yet to watch this D&D live show, skip to the next sub-chapter to avoid spoilers.
Well-known locations in the Leviathan include Maelstrom’s Maw, a supply shop of sorts where ships are dismantled and looted for their materials. It is run by warforged bosun Jamina Joy, who has the delicate job of keeping the city afloat. Jamina has already made appearances in Episode 5 through 8 of Dimension 20 LIVE.
Leviathan is also house to the Four Castles, a violent part of town where citizens will gladly take each other out for half a shilling, or control of the street’s block. Close to the Four Castles lies the cursed Sternwood forest, plagued by beasts, monsters, distorted trees, and human remains.
Further South, Cannon Court has used shipwrecks and hulls to form a large dwarven-style subterranean neighbourhood full of dwarves and gnomes. In contrast, Galleyard is a lovely area that includes The Gold Gardens (notable NPC Garthy O’Brien‘s house of debauchery), and forms the nexus of the city. With a reportedly New Orleans type architecture, the city centre is bustling with diverse peoples.
Connected to the city’s mosque by way of dagger, Gibbety Square is adorned with the head of a former pirate king, put on display by Fabian Seacaster‘s father Bill Seacaster. It includes a sign that reads “No kings for a captain.” Near Gibbety Square lies Aftward, home to a tower of prison blocks neatly named the Row and the Ruction. Atop Aftward stands Crow’s Keep, housing the Compass Points Library and the Ramble (a place for elder pirates to engage in decision-making).
Lastly, Poop City is, you guessed it, the name deemed worthy of the wealthiest and most luxurious neighbourhood in Leviathan. Why not!
• Read more about Leviathan’s neighbourhoods on Fandom
Pirates of Leviathan’s Intrigue: An entire city at stake
The trailer is peppered with clues that offer some insight in terms of location, plot, and player characters. Those unfamiliar with the island of Leviathan know it now as a “behemoth of shipwrecks”, and the “Jewel of the Sea”, perhaps foreshadowing the location’s innate dichotomy: a monstrous creature, and yet a precious treasure.
At the start of the clip, an NPC ominously utters the words “Take her body to the Sternwood with the others”, possibly implying that a female NPC has either died, or that her body is somehow affected or cursed. “The others” suggests that there are several, if not many, people in Leviathan who have lost their lives or have been met with some terrible fate; rough enough to have them be dragged to Sternwood, a place apparently adequate for storing bodies. Eerie.
Our Intrepid Heroes, here Buccaneer Buddies, have been informed that “all of Leviathan is in a heaping helping of trouble.” Such a sinister statement surely supposes that the torments bedevilling the city are greater than a squabble limited to a singular NPC or set of NPCs. The combination of bodies being taken to a cursed forest and the omen that all of Leviathan is somehow affected might indicate that something larger is at stake. This begs the question – who, or what, is determined to take down an entire city? And why? If the name is any hint, perhaps a sea serpent, but knowing the DM’s background in philosophy, it’s likely a nod to Thomas Hobbes’ Leviathan in which the author proposes absolute sovereignty as a necessary evil. That’s not to say the two Leviathans are mutually exclusive. Absolute sea serpent sovereign end boss? Yes please!
Player Characters in Pirates of Leviathan
The trailer also sheds light on the kind of PCs and party mix viewers can expect, and how they might complement each other, or clash. Heads up – some class, race, and level spoilers ahead in this subchapter! According to Fandom, all PCs are level 5 residents of Leviathan. No one is a newcomer!
• Barbarella “Bob” Sasparilla Gainglynn, played by Denver by Night’s Krystina Arielle is an Aasimar multi-classing as a Level 3 College of Lore Bard, and Level 2 City Domain Cleric (Unearthed Arcana). Bob’s chirpy voice and good-natured spirit come through in the trailer: “Sometimes you just need a little diplomacy”. A nice, and perhaps unassuming, Bard-Cleric, Bob seems to be the antithesis of typical pirate life.
• Cheese, played by Roll 20’s Carlos Luna, is a Forest Gnome School of Necromancy Wizard. Though he might have a fighter side viewers have yet to witness, the trailer has him pinned down as the party’s nervous adventurer in touch with his emotions. “Oh god,” and “I cry all the time” set the tone for this PC. Then again, being a life-reaping necromancer does warrant constant crying.
• Jack Brakkow, played by Critical Role’s Matthew Mercer, is a Ratfolk Path of Ancestral Guardian Barbarian. The trailer portrays Jack as a bit rough around the edges, and maybe a bit of a loner: “Sorry child, I don’t have friends.” He is also heard shouting quite aggressively “You bastard – I can’t afford a new wall!”, suggesting that damage was done to his property, and that he isn’t financially in a position to repair it. Yar – this PC could be in it for the coin!
• Marcid the Typhoon, played by Dungeons & Dragons’ B. Dave Walters, is a Bugbear Gloomstalker. Perhaps diplomatic in nature like Bob, Marcid seems partial to some negotiation: “We can talk it out, mate.” As a Gloomstalker, it might be safe to assume that he is a careful character, in the know when it comes to the darkest of places in Leviathan. His warning “Loose lips sink ships” might be a reference to his experience overhearing conversations. Beware!
• Myrtle the Bitch, played by Saving Throw’s Aabria Iyengar, is a Merfolk Tempest Domain Cleric. Myrtle’s profile is a whirlwind of mystery that is to die for. Her Fandom description reveals that she “sinks ships to appease her god”, and that her favourite colour is “Blood”. In Dimension 20’s trailer, an NPC (perhaps her god) addresses her with “You’ve sent many souls down to my hungry mouth”. This same person or creature, one could suppose, also responds to her with “Quite worth the spells…”. Is there an actual Leviathan in Leviathan? Is Myrtle a warlock? Only time will tell.
• Sunny Biscotto, played by Critical Role’s Marisha Ray, is an Aarakocra Oath of Devotion Paladin. Although Sunny didn’t say too much in the trailer, her “Whoah wait!” could be a quick nod at a Paladin’s usual pre-conflict behaviour: use your words, not your fists! Or wings. As an Oath of Devotion Paladin, Sunny would typically be bound to the highest of ideals, virtue, and order, and it’ll be interesting to see how she gets along with PCs such as Myrtle, Marcid, and Jack.
Of course, it would be a sin not to mention that the experienced (guest) cast and crew of Dimension 20 always manage to circumvent the usual stereotypes, tropes, shallow motivations, and black-and-white character choices. If Pirates of Leviathan is anything like the rest of D20’s Quests, then its PCs are sure to be multilayered, emotionally complex, and lots of fun.
Dimension 20’s Pirates of Leviathan premieres September 16 on Dropout TV.