Dimension 20 originated as a production for Dropout, a streaming service launched by CollegeHumor in 2018 to deliver content with R-rated material or an unusual format.

Mulligan cited a number of existing tabletop shows as inspiration for Dimension 20, including Not Another D&D Podcast (NADDPod), The Adventure Zone and Critical Role.

Episodes of Fantasy High: Sophomore Year were streamed live on Twitch, unlike the pre-recorded and edited style of other campaigns on Dropout.

[6] The launch of the show took place amid financial troubles at CollegeHumor, which had suffered from a pivot to Facebook video in the late 2010s based on inaccurate metrics.

[14] A Fantasy High auction in 2024 donated 100% of profit to the Palestine Children's Relief Fund, and for the first time included scenery pieces and segments of the Dungeon Master's screen.

[17] In August 2023, Reich announced that all Dropout shows had resumed production, as it was determined that their "New Media Agreement for Non-Dramatic Programming" was under a non-struck SAG-AFTRA contract.

[24][25][23] In January 2025, Dimension 20 announced that the Fantasy High campaign would receive a comics adaptation on Webtoon; it is scheduled to run for 61 episodes starting in the spring of that year.

[28][29] Intrepid Heroes campaigns feature Mulligan as the Dungeon Master, along with players Emily Axford, Ally Beardsley, Brian Murphy, Zac Oyama, Siobhan Thompson, and Lou Wilson.

[30] A 2024 Time Quangle live tour in the UK and Ireland also featured the Intrepid Heroes cast and acted as a crossover between the main campaigns.

[81] In the late 2010s, the format pioneered by Critical Role — with the cast performing live in a full table multi-camera composite — had come to dominate actual play.

[82] He described it as a "crystal cave" that "can go from a frosty fantasy feeling" to "more of a Fortress of Solitude, Sci Fi vibe", which allows the show to shift genre as needed.

[83] In an interview, director Michael Schaubach highlighted that Kenny Keeler, the original director of photography, started with a Dana dolly and that "in the years since, Schaubach has overseen the quest for a different, even more articulable jib, updated cameras, an LED projection system that can add shadows and animation onto the walls of the set, and, in Burrow's End, audio recordings presented as artifacts".

[85] Graham Sheldon, the director of photography for Neverafter (2022), stated that they typically used five cameras when filming the campaign with a setup that allowed closeup overhead shots of the maps and miniatures.

Sheldon commented that while there is pre-planning to give "everyone a good sense of where things might go" during filming, the improvisational aspect of the show often required people "to hop on additional cameras to follow the action".

The format does add cost to the production, but the approach allows for the removal of pauses and the inclusion of post-production elements such as character art, illustrations, and footage of the battle terrain.

Beginning with A Crown Of Candy, Dropout began airing a Dimension 20 Q&A and talkback show called Adventuring Party, in which the cast would discuss the most recently recorded episode.

[93] Moises Taveras, for Paste in 2023, also highlighted the improvisational nature of the show and how the game mechanics of dice rolls "sets Dimension 20 apart from the rest of TV".

[8] Taveras stated that "I can't predict a thing that's going to happen thanks to the insanely successful marriage of this mechanic to the cast's improvisational skills.

There's nary a moment, whether it be a rousing victory or an utter defeat, that doesn't propel these characters forward in some way and carve out a unique, player-driven story.

[8] In 2023, Lauren Coates of Polygon highlighted how the anthology format allows Dimension 20 to reinvent itself and span "a vast variety of genres, styles, and tones" with their seasons "consistent in their ability to deliver across comedic, narrative, and emotional fronts".

[94] Coates commented that "as funny as the series is, it isn't just Dimension 20's sense of humor that makes it so beloved; it's the consistently heartfelt, poignant storytelling that accompanies it.

[29] Cruz also highlighted that it is not only "the familiar narrative hooks" which make the show "so accessible" but also "its strong focus on diverse voices and socially relevant themes woven into the framework.

[62] Zeoli highlighted that the cast "experiences the range of emotions your first D&D campaign can evoke" with the season offering "an easy and entertaining access point for queer people who have never felt safe entering D&D's complex (and occasionally infuriating) world of rules, lore, and role-play.