With over twenty seasons to its name, Dimension 20‘s varied and hilarious seasons have helped make DropOut one of the best streamers available. Dimension 20 is similar to other actual play shows like Critical Role, where the cast of talented performers improvise their way through a massive story bolstered by 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 ten seasons of Dimension 20, ranked.

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-users — 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.

5

Dungeons And Drag Queens

Season 18

“Dungeons and Drag Queens” is one of the shortest seasons of Dimension 20, only running for four episodes. However, the unique cast comprised entirely of Drag Queens prove to be perfectly suited for a short and silly exploration of the underworld. The seasons focuses on Troyánn, Princess, Gertrude, and Twyla, otherwise known as the Questing Queens. “Dungeons & Drag Queens” highlights how flexible the show can be, which (outside Mulligan as the DM) features an entirely new cast for the show.

The four performers quickly adapt to the improvisational elements of the show, bringing unique perspectives to the series thanks to their high-energy performance and play. As famous drag queens in real life, the four players adapt to the fantastical and silly world with ease. The foursome (especially Twyla) are particularly great additions to Dimension 20’s pantheon of weirdos, whose antics throw even a seasoned DM like Mulligan for a loop. While the adventure may have been relatively short, the show will be returning to the setting with the upcoming “Dungeons & Drag Queens” season 2.

4

A Court Of Fey and Flowers

Season 15

DM’ed by Aabria Iyengar, “A Court of Fey and Flowers” is a unique entry in Dimension 20 for actively resisting combat as a key element. Instead, inspired more by the works of Jane Austen than expansive fantasy settings like Lord of the Rings or Harry Potter, “A Court of Fey and Flowers” ends up being a far more cerebral and character-driven season. The story focuses on a high-society ball being held in the Fey Realms, with Chirp, Gwyndolin, Hob, Delloso, Andhera, and Squak contending with all sorts of romance, intrigue, and danger.

The goofy approach to high romance and drama benefits the season in the long run, with surprising connections being fostered between the player characters. It’s also a consistently hilarious season thanks to some truly absurd decisions made by Mulligan, Wilson, and Axford, who use their characters to push the comedy as far as possible, up to and including Mulligan eating an actual feather at the table. It’s a silly and supremely sweet season, and arguably Dimension 20‘s best showcase for how well romance can work in this show format.

3

Fantasy High (Freshman Year)

Season 1

“Fantasy High” is the first and perhaps most wide-reaching season of Dimension 20. Described by DropOut as “John Hughes meets D&D,” the (currently) three-season series focuses on six students dubbed the “Bad Kids” as they attend the Aguefort Adventuring Academy. While Sophomore and Junior Years are also fantastic, the first season of the show is the perfect bedrock for what the series has become. The loose improvisational approach enhances the comedy as Fabian, Kristen, Gorgug, Adaine, Riz, and Fig explore the world of Spire, a fantastical approximation of the typical suburban setting of most teen-centric films.

The unexpected swerves taken by both the players and DM Brennan Lee Mulligan add to the unexpected tense moments between comic digressions, with the sheer scale of the universe benefiting the comedy in impressive ways. What elevates season 1 above the others is the surprisingly open and vulnerable emotional moments, like Adaine’s late-game panic attack. There’s a reason this season got three more seasons, as well as a number of spin-offs like “The Seven” and “Pirates of Leviathan.”

2

Neverafter

Season 16

Serving as Dimension 20’s self-proclaimed “horror” season, “Neverafter” focuses on twisted versions of classic folklore. When the stories of Cinderella, Puss in Boots, the Frog Prince, Pinocchio, Red Riding Hood, and Timothy Goose become increasingly warped, they find themselves exploring a fantastical realm filled with malicious monsters and unspeakable evils. While “Misfits and Magic” uses the meta-elements of the story to satirically poke fun at the source material, “Neverafter” fuses that self-aware storytelling with mystic and cosmic horror that would feel perfectly in-place alongside the creations of Guillermo Del Toro.

Nevertheless, the show retains its core focus on character-driven comedy and drama, with the show’s central cast delivering some of their finest dramatic work across the course of the season. The comedy likewise remains as solid as ever, including some of the best digressions from the cast. This is also the season where following along with the Behind-The-Scenes show Adventuring Party is most recommended, as the interplay between the cast in the aftermath of such high drama is often just as funny as the show itself.

1

A Starstruck Odyssey

Season 13

Set in the universe of Starstruck, a graphic novel series by Elaine Lee (and Brennan Lee Mulligan’s mother), the space opera “A Starstruck Odyssey” centers around the mercenary crew of a hot dog-shaped spaceship known initially as the Red Hot as they try to survive a vast, absurd, and incredibly dangerous universe. Sundry Sidney, Barry Syx, Riva, Gunnie, Margaret, and the Skipper are some of Dimension 20’s best characters, a collection of sci-fi weirdos with untapped potential and hilarious expectations about the universe. The season balances cosmic stakes with phenomenal character growth, filling out the epic with deeply emotional explorations of the self.

It also features some of the series’ best action, with the crew of the Red Hot using creative methods to dish out (and survive) truly staggering threats. The season plays with Dimension 20‘s underlying themes in compelling ways, with a strong moral about the strength of the collective and resistance to reckless capitalism, ruthless control, and unearned power. It’s also, like every season of Dimension 20, a frequently hilarious affair. Bolstered by the show’s core cast firing on all cylinders and some of Mulligan’s best work as a DM, “A Starstruck Odyssey” is the best season of Dimension 20.