Dropout’s Dimension 20 has returned for its 26th season and ninth to feature the main cast of Intrepid Heroes. The tabletop role-playing show is jumping into the steampunk genre for the first time in this campaign, titled Cloudward, Ho. The setting presents an interesting challenge for Dungeon Master Brennan Lee Mulligan and players Siobhan Thompson, Ally Beardsley, Brian Murphy, Emily Axford, Zac Oyama, and Lou Wilson, who are sticking with Dungeons & Dragons 5e. Though D&D can be changed and adapted to fit pretty much any genre, mechanically the system is primarily built for extremely magical, high-fantasy stories. And there are traditionally not a lot of fantastical people or straight-up magical wizardry in steampunk, as evident by how Cloudward, Ho’s cast are all purposefully limiting themselves to playing as humans and non-spellcasters.

Cloudward, Ho sees two wannabe explorers–one concerned with securing fortune, the other eager to find their long-lost grandmother–teaming up and recruiting four members of a long-disbanded airship crew for one last adventure to find a fabled continent believed to have disappeared in the distant past. The first episode has strong Atlantis: The Lost Empire and Treasure Planet vibes, especially regarding how delightfully absurd many of the characters are.

In the new season, Thompson and Oyama are playing Fighters named Vanellope Chapman and Daisuke Bucklesby, respectively; Beardsley is playing as a Rogue named Olethra Macleod (though Episode 1 feels like it heavily implies Olethra will multiclass into something like Artificer before all is said and done); Axford is playing an Artificer named Marya Junková; Murphy is playing as a Pugilist named Maxwell Gulch; and Wilson is playing a Ranger named Montgomery LaMontgommery. No magic-manipulating Sorcerers, god-worshipping Clerics, or any of D&D’s six main spellcaster classes–most of which have been regular picks for a few of the players, like Axford and Beardsley.

“Something that Brennan said as we were doing character creation was no pure magic users,” Thompson told me. “Either no magic or [magic had to be] secondary, and that’s just a fun restriction to put on yourself. There’s so many [D&D] subclasses at this point, we’re never going to be able to play them all, [so we] still had a lot to work with.”

“The magic had to come through technology [instead], and that was a fun way to tell this story,” Beardsley added. “[We could ask,] ‘What is exploration? What is technology? How is [technology] corrupted and manipulated [when] people go rogue?’ That was pretty fun, but I was a little worried about my character’s makeup and being lower level and not having spells. I was just, ‘Oh gosh, how do I map this out for myself?’ But it was awesome. There was a lot of new tech and there [were] a lot of new avenues of storytelling that I feel like Brennan went down when it came to [mechanics with] widow’s breath and chemicals and inhalation and chemical dependency and stuff like that–I loved finding [those] new things.”

This season’s characters most remind me of those designed for 2019’s The Unsleeping City (magical superheroes operating in secret in New York City) and 2020’s A Crown of Candy (what if Game of Thrones existed in Candyland?), where part of the cast is roleplaying as characters who have an established history with each other and some of the setting’s secrets, while the other players are playing as characters who are inexperienced newcomers. Thompson, Axford, Oyama, and Wilson are all playing as characters who are older and once flew together on the same airship for years, while Beardsley and Murphy’s characters are younger, more sheltered, and inexperienced when it comes to a life of adventure. Their two characters meet the other cast’s characters basically for the first time in Episode 1 (all of the characters technically met once years prior to the adventure’s start, but while the other four were adults, Maxwell was barely older than a toddler and Olethra was a newborn baby so it feels like that meeting doesn’t really count for them).

“We wanted to tell the story of jadedness and just aging, [as well as], do you age with grace when you [attain] celebrity?” Beardsley said. “That’s a totally fine story to tell [on its own], but we also wanted to have one more wrench thrown into it: What if we also have young up-and-comers and they get to meet their heroes and they’re the ones trying to shake them out of that stupor of, ‘Ah, f**k it. I give up. That was too hard.’ It’s like the KISS documentary–they all go to therapy together [and you see how] it’s really hard to work in a group professionally and stay together with the same group of people through decades, let alone on a ship fighting for your life.”

Thompson added: “Also that a group of people can go through the exact same experience and have very different experiences within that [and] even have very different reactions to those experiences–[outcomes] that are all interesting and valid and nobody’s wrong.”

Having only watched the first episode of Cloudward, Ho ahead of the season’s premiere, I’ve only seen snippets of this dynamic so far, but I’m enjoying the mystique it’s already creating. There have been numerous side remarks and quick references to past adventures between Vanellope, Marya, Daisuke, and Montgomery, and much like Olethra and Maxwell, we, the audience, are outsiders to these conversations and don’t fully grasp what’s happened to the more experienced members of the crew. And I want to know what’s going on, especially whatever is happening with Axford’s Marya. The Artificer is notably younger than the other experienced members of the group, and the now haunted and vengeance-driven tinkerer is a far cry from the confidant and gun-happy explorer that we saw in a brief flashback at the start of Episode 1. Whatever happened to Marya seems to have messed her up far more than the other characters.

“I don’t really know what Emily’s take away from this season ultimately was, but she really inspired me because I think she picked a storyline that she kind of didn’t want to tell,” Beardsley said. “And you could watch that [affecting] her throughout the season where she was so moved and she was so immersed into her character and I was like, ‘Wow.'”

“It’s such a good performance,” Thompson added.

“I’m just like, ‘I hope she had fun doing that.'” Beardsley concluded, laughing. “I’m positive she did. She was amazing. It’s a really fun Emily season. It’s a really fun ‘everyone’ season [and] I loved everyone’s characters that they came up with, but Em’s was really fun.”

Cloudward, Ho is now live on Dropout, the best streaming service and the only one you should have if you can only afford one streaming service these days. New episodes of the 20-episode season will premiere on Wednesday at 4 PM PT / 7 PM ET. The first episode will be released on Dimension 20’s YouTube channel on June 11, but all other episodes will remain exclusive to Dropout.

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