With over twenty seasons to its name, TTRPGs like Dungeons & Dragons and Kids on Bikes. However, whereas Critical Role campaigns can last over a hundred episodes, Dimension 20 frequently hops between casts and settings for shorter seasons that range between 4 and 20 episodes. Trying to figure out which seasons are the best can be deceptively tricky.

Make no mistake, each of the show's over twenty seasons have their 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 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. These are the top fifteen seasons of Dimension 20, ranked.

15 Shriek Week

Season 12

Dimension 20 is so beloved among the many TTRPG shows out there due to how unique the settings of many of its campaigns are, and season 12, Shriek Week, is one of the best examples of this. DM'd by Gabe Hicks, Shriek Week had a reduced group with only four players due to COVID-19 restrictions, though this ended up creating a more intimate viewing experience compared to some other seasons with a larger group.

Shriek Week was also the first season of Dimension 20 not to include Brennan Lee mulligan in any capacity (and only the second to have a guest DM). Shriek Week is set at Bram University, a school where monsters can enroll and learn about humanity with a goal to integrate better into human society.

Shriek Week was full of many nods and cameos from monsters of real-life myths and legends. Legendary horror author Bram Stoker founded Bram University alongside Dracula, for example. This spooky flavor combined with veteran cast Ally Bearsley, Dani Fernandez, Ify Nwadiwe, and Lily Du led to the four-episode season being one of the best bingeable short-watches in Dimension 20 history.

14 Tiny Heist

Season 5

Season 5, Tiny Heist, was the second Dimension 20 side quest, and like Shriek Week, it stands out primarily due to its incredibly innovative setting. Tiny Heist involves the players taking on characters of an extremely minuscule size, like fairies, bugs, and even living toys. The general idea is more-or-less Honey, I Shrunk The Kids, though with a heist adventure thrown into the concept.

To make this combination of heist adventure and shrinking story even more hilarious, the group's goal is to find and steal a roll of quarters. The various boards and maps add to the flavor, and still serve as some of the best examples of Dimension 20 using these elements of TTRPG's to enhance the viewing experience.

Tiny Heist takes inspiration from a variety of sources alongside the simple idea of adventuring as tiny characters in the modern world. Many aspects are clear nods to existing movies, shows, and games, such as the talking toys being reminiscent of Toy Story. Brennan Lee Mulligan leads as the DM, which (as fans of Dimension 20 know), more-or-less guarantees it will be a satisfying adventure to watch throughout. Adding to the hilarity is the presence of four of the McElroy brothers, whose natural chemistry with one-another leads to many laugh-out-loud moments.

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.

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 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 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 13

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 includes Candia, land of sugards, Vegetania and Fructera for vegetables and fruits, and even The Dairy Islands.

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 bomastic 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.

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.

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.

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's" tight focus helps 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 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 remains 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 tying to establish peace between the material and the sleeping worlds.

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-s — Jammer, Dream, Sam, and Evan — to the school as older teenagers.

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.