15 Best Dimension 20 Seasons, Ranked

More than two dozen seasons to its name, Dimension 20 has helped make DropOut a destination for actual-play storytelling. Like Critical Role, the series follows talented performers improvising their way through adventures shaped by tabletop role-playing games. Still, where some actual-play campaigns run for more than a hundred episodes, Dimension 20 regularly changes its cast, setting, and even game system. This allows shorter seasons to offer sprawling, massive variety. This makes selecting the best rather tricky.

Make no mistake, each of the show's seasons has its own strengths. The nature-focused "Burrow's End" and "Mice & Murder," the noir-style Inside Out world of "Mentopolis," the monster college of "Shriek Week," and "Tiny Heist's" fairy-folk heist are all strong solo-season stories, and the various other seasons and spin-offs of the ranked shows are also hilarious and affecting. Despite that overall strength of the show as a whole, some seasons are just pound-for-pound more compelling, dramatic, and hilarious than the rest.

15 City Council Of Darkness

Season 28

City Council of Darkness gives the Intrepid Heroies a new kind of fantasy conundrum—running a small town while also being vampires. Set in Oregon, this season follows a group of outcasts tasked with establishing their power in a place where local politics, public appearances, and the need for blood can all become equally pressing concerns. Right there on the surface, this is pretty hilarious.

City Council Of Darkness Cast	Role In City Council Of Darkness
Brennan Lee Mulligan	DM
Emily Axford	Vesper Childers
Ally Beardsley	HJ Wingstreet
Brian Murphy	Mitch Frederick, "Darkness Man"
Zac Oyama	Zaeth Bondana
Siobhan Thompson	La Contesse Madelaine d'Artois
Lou Wilson	LaVonte Worthy

This season is unique compared to others since it uses Vampire: The Masquerade instead of the typical Dungeons & Dragons rules of other campaigns. The system allows the cast supernatural abilities with a different sort of feel. It's thrilling and intense, while remaining entirely humorous.

The 14 episodes of this season leave plenty of room for the cast to develop their characters, all while leaning into the outrageous contrast between gothic vampire drama and the Parks & Rec chaos of town council. Seeing these characters attempt to keep their vampire issues under wraps in a small town setting is simply everything it should be.

14 Cloudward, Ho!

Season 26

The adventures of "Cloudward, Ho!" are set aboard the airship Zephyr, and the players take on the characters of members of the original crew. The gang is on the hunt for their missing leader, Professor Comfrey MacLeod, whose disappearance inspired them to all come back together after years off the ship.

Cloudward, Ho! Cast	Role In Cloudward, Ho!
Brennan Lee Mulligan	DM
Zac Oyama	Daisuke Bucklesby
Emily Axford	Marya Junkova
Lou Wilson	Montgomery LaMontgommery
BRian Murphy	Maxwell Gotch
Siobhan Thompson	Venellope Chapman
Ally Beardsley	Olethra MacLeod

There was little question that a steampunk-inspired season would gain a lot of attention and approval. This world is new and fresh, and Mulligan gives the cast an enormous amount of room to investigate. The Zephyr serves as the home base and central hub, but the mystery of this campaign carries the cast in several different directions.

Cloudward, Ho! also created some truly excellent dynamics between the cast and characters. The Intrepid Heroes had plenty of time to reconnect and explore their dynamic, all while their adventure kept the storytelling moving in the right direction.

13 Mice & Murder

Season 9

Mice & Murder, the 9th season of Dimension 20, stands out for several reasons, though a key one is that it was filmed during the COVID-19 pandemic restrictions, meaning that all 10 episodes only have the players appearing remotely. While this definitely detracts from Mice & Murder compared to the many seasons of Dimension 20 where the cast appears in person, it does add something endearing for many viewers too.

Mice & Murder Cast	Role In Mice & Murder
Brennan Lee Mulligan	DM
Katie Marovitch	Gangie Green
Sam Reich	Buckstar S Boyd
Rekha Shankar	Daisy D'umpstaire
Raphael Chestang	Vicar Ian Prescott
Ally Beardsley	Lars Vandenchomp
Grant O'Brien	Detective Sylvester Cross

Lockdowns and other restrictions during the COVID-19 pandemic allowed many to discover TTRPG's like Dungeons and Dragons for the first time, playing with one-another on video messaging platforms like Zoom, Teams, and Discord. This has given Mice & Murder something of a nostalgia factor for many Dimension 20 fans, as it brings back memories of similar gaming experiences they also had during the pandemic.

Most of the cast of Mice & Murder were newcomers to Dungeons and Dragons, which also led to some hilarious moments. The setting is especially interesting too, as it's set in the 1905 of an alternate universe where the earth is inhabited by anthropomorphic animals. Throw in a muder mystery where the party have to solve a murder at Squire Badger's 60th birthday party, and Mice & Murder makes for a unique and charming Dimension 20 season, even if most fans don't consider it the best.

12 The Seven

Season 11

For fans of Disney princesses, The Seven is likely the best season of Dimension 20, as the side quest has a great deal of fun lambasting the various tropes of the leading ladies of classic Disney movies — as well as a healthy amount of parodying teen movies and the high school experience in general. The Seven takes place in the Fantasy High setting from the first-ever Dimension 20 campaign, though it focuses specifically on the characters of The Maidens.

The Seven Cast	Role In The Seven
Brennan Lee Mulligan	DM/Zelda Donovan
Aabria Iyenga	Antiope Jones
Rekha Shankar	Katja Cleaver
Becca Scott	Penny Luckstone
Erika Ishii	Danielle Barkstock
Isabella Roland	Ostentatia Wallace
Persephone Valentine	Sam Nightingale

The adventuring party in The Seven were all female players, which added to the hilarity as each was able to draw on their own personal experiences in high-school. While this Dimension 20 season may not be the most serious (even by the standards tongue-in-cheek approach to Dungeons & Dragons that makes the entire show so popular), its 10 episodes manage to be laugh-out-loud funny without sacrificing a cohesive narrative.

The Seven was the second season to be filmed in-person with all cast members present after the COVID-19 pandemic, though with some restrictions still in place there remains a notable absence of group shots. This season was also notable for making use of 3D virtual maps to represent the action taking place, rather than real maps on the table or 2D representations.

11 A Crown Of Candy

Season 5

The third Intrepid Heroes campaign from Dimension 20 was season 6 of the show overall, and it featured one of the most innovative settings for a Dungeons & Dragons adventure so far. A Crown of Candy took place in the world of Calorum, a world where each kingdom represents a different food group in the nutritional pyramid. These include Candia, land of sugars, Vegetania and Fructera for vegetables and fruits, and even The Dairy Islands.

A Crown Of Candy Cast	Role In A Crown Of Candy
Brennan Lee Mulligan	DM
Lou Wilson	King Amethar
Emily Axford	Princess Jet Rocks
Zac Omaya	Chancello Lapin Cadbury
Ally Beardsley	Liam Wilhelmina
Siobhan Thompson	Princess Ruby Rocks
Brian Murphy	Sir Theobald Gumbar

A Crown of Candy is one of the Dimension 20 seasons that epitomizes what makes the show so popular. Despite the map and general aesthetic making it seem as though the adventure takes place somewhere not dissimilar from the Candy Kingdom in Adventure Time, A Crown of Candy manages to perfectly balance bombastic weirdness with solid fantasy roleplaying and epic adventure.

Surprisingly too, given the bubblegum aesthetic of the maps and set pieces, A Crown of Candy was also one of the deadliest Dimension 20 campaigns as far as the player characters are concerned. Every player had to create a backup character just in case (though only two ended up being used). All in all, A Crown of Candy remains one of the most unique seasons of the show, and it would likely rank higher were it not for later returns to the world of Calorum doing the setting even more justice.

10 Coffin Run

Season 14

DM'ed by Jasmine Bhullar of DesiQuest, "Coffin Run" is one of the most consistently silly seasons of Dimension 20, with a cast of oddballs that stand out even from the rest of the show's vast roster of characters. "Coffin Run" focuses on the allies of Count Dracula as they work to protect the wounded Count from several threats.

Coffin Run Cast	Role In Coffin Run
Jasmine Bhullar	DM
Erika Ishii	May Wong
Carlos Luna	Wetzel
Zac Oyama	Squing
Isabella Roland	Dr. Aleksandr "Sasha" Astrovsky

Getting to play the Fang Gang as a bunch of openly evil vampires gives the show a unique comic edge even when compared to something like "Escape from the Bloodkeep". Zac Oyama's Squing is one of Dimension 20's most bizarre and funny creations, an ancient vampire with the body and maturity of a child.

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The rest of the cast is equally solid, with May, Sasha, and Wetzel each bringing unique energy to the season. Bhullar also matches their skills well, particularly with her surprisingly effective wildcard Florina. An orphan the Fang Gang encounters, Florina and her multi-pronged presentations about why they should hire her highlight the relentless comic energy that propels "Coffin Run."

9 Escape From The Bloodkeep

Season 2

A breakneck pace full of unexpected lethal turns helps keep the hilarious "Escape from the Bloodkeep" on track. The first of Dimension 20's "Side Quest" seasons that typically work as stand-alone stories, "Escape from the Bloodkeep" focuses on the six lieutenants of Zaul’nazh, a riff on Sauron from The Lord of the Rings.

Escape From The Bloodkeep Cast	Role in Escape From The Bloodkeep
Brennan Lee Mulligan	DM
Erika Ishii	Lilith
Matthew Mercer	Kraz-Thun (aka Leiland)
Ify Nwadiwe	Markus St. Vincent
Rekha Shankar	Maggie
Mike Trapp	Sokhbarr
Amy Vorphal	Efink Murderdeath

After he's suddenly destroyed thanks to the machinations of the Forces of Light, it falls to Efink, Sokhbarr, Lillith, Markus, Leiland, and Maggie to restore him and hold back the forces of light. The high stakes of the season are established early, with a number of shocking turns in the first battle turning the Tolkien parody into a bloodbath.

What elevates the season is the core cast and their interplay with Mulligan. The manic Avanash and dim-witted Percival are both hilarious NPCs on their own, but it's the cheery halfling Galfast Hamhead and her unexpected rivalry with Matthew Mercer's Leiland that stands out as one of Dimension 20's single best comedy duos.

8 The Ravening War

Season 17

The prequel to the previous season, "A Crown of Candy," "The Ravening War" tightens its focus to help keep the sprawling fantasy epic grounded. Both stories are set in the land of Calorum, a take on Candyland imagery with a Game of Thrones tone. While "A Crown of Candy" focuses on a power struggle for the throne centered around House Rocks and their allies.

The Ravening War Cast	Role in The Ravening War
Matthew Mercer	DM
Anjali Bhimani	Queen Amangeaux Epicée du Pech
Aabria Iyengar	Karna Solara
Brennan Lee Mulligan	Bishop Raphaniel Charlock
Zac Oyama	Colin Provolone
Lou Wilson	Thane Delissandro Katzon

"The Ravening War is set years before and reveals how a massive conspiracy set the stage for the events that occurred in "A Crown of Candy". The only season of Dimension 20 so far DM'ed by Critical Role's Matthew Mercer, "The Ravening War" benefits from a tight character focus.

While the prior season set in Calorum established the massive world, the sheer scale of the cast could make things tricky to follow. By contrast, "The Ravening War" has a compelling cast of five central characters who find their morals tested by promises of power and purpose that nevertheless remain hilarious. Already a renowned DM, Mercer fits perfectly into Dimension 20's silly and loose approach to epic storytelling.

7 The Unsleeping City (Chapter II)

Season 8

Set in a mystical version of New York City, "The Unsleeping City" is a two-part series that focuses on six unexpected heroes who become known as the Dream Team. Plug, Sofia, Ricky, Kingston, Kugrash, and Misty find themselves trying to establish peace between the material and the sleeping worlds.

The Unsleeping City: Chapter II Cast	Role in The Unsleeping City: Chapter II
Brennan Lee Mulligan	DM
Emily Axford	Sofia Lee
Ally Beardsley	Pete "Plug" Conlan
Brian Murphy	Cody "Night Angel" Walsh
Zac Oyama	Ricky Matsui
Siobhan Thompson	Iga Lisowski
Lou Wilson	Kingston Brown

Ethereal and grounded at the same time, "The Unsleeping City" represents some of the most expansive and exciting world-building in all of Dimension 20. Season 1 is honestly just as strong as the second season and does great work building up the setting. However, characters like Cody Walsh and villains like Null elevate season 2 to new comic and supernatural heights.

Even being filmed during the height of the pandemic (forcing the season to be largely conducted remotely) couldn't bring down the energy for an exciting season. The Unsleeping City will return with a live show in Madison Square Garden, which could build off the events of the previous seasons and potentially push the world forward in unexpected ways.

6 Misfits and Magic

Season 10

The first campaign DM'ed by Aabria Iyengar, "Misfits and Magic" is one of the best parodies of Harry Potter out there, with a keen sense of commentary on the source material that never loses sight of the characters. Taking place at a magical academy in Britain, "Misfits and Magic" focuses on a pilot program to bring four American magic-users — Jammer, Dream, Sam, and Evan — to the school as older teenagers.

Misfits and Magic Cast	Roles in Misfits & Magic
Aabria Iyengar	DM
Erika Iishi	Karen Keiko Tanaka (aka Dream)
Brennan Lee Mulligan	Evan Kelmp
Danielle Radford	Sam Black
Lou Wilson	Whitney Jammer

A decidedly meta-take on the premise, the four teens are largely aware of real-life pop culture like Harry Potter, setting up an effortlessly funny back-and-forth between Aabria and the cast. Dream and Sam are uniquely specific and universally silly teens, and Jammer is one of the best examples of Dimension 20's surprising gallery of well-meaning goofballs.

Evan is the highlight, though, a reluctant and exhausted "dark one" who just wants to be left alone. One of a handful of times Mulligan has been a member of the cast of a season, his Evan is simultaneously one of the show's most tragic and silly characters.