Lou Wilson ‘Dimension 20: Cloudward, Ho!’ Interview

SPOILER ALERT: This story contains spoilers for Episode 1 of “Dimension 20: Cloudward, Ho!” streaming now on Dropout.

As one of “Dimension 20’s” regular cast members (a.k.a. “Intrepid Heroes”) Lou Wilson has played everything from a cyborg engineer to a foul-mouthed wooden puppet. But for the first time in nearly three years, “D20” fans meet a new Lou Wilson player character (PC) in “Dimension 20: Cloudward, Ho!” which hit indie streamer Dropout Wednesday.

The new series, which debuted just days after “Dimension 20’s” live show at the Hollywood Bowl, is an Indiana Jones-meets-Jules Verne-style adventure installment of the role-playing game TV show that follows the crew of an airship as they “Join forces and take to the skies in search of the missing Professor Comfrey MacLeod, [venturing] off to a fantastical world of machine wonders and perils known as Gath.”

Ahead of the “Dimension 20: Battle at the Bowl” live show and the premiere of “Dimension 20: Cloudward, Ho!,” Wilson spoke to Variety about the historical figure that inspired his new character, whether or not he wants to DM a season of “Dimension 20” and returning to the world of “Fantasy High” for a live show.

“On the cast side, we were really excited at the idea of getting back into that place of discovery,” Wilson said. “We love returning to seasons because we get to evolve old bits, in the way that so much of D&D is us bringing ourselves as people to the art form. It’s fun to re-meet those things in new ways with new energies.”

Wilson, his fellow Intrepid Heroes (Emily Axford, Ally Beardsley, Brian Murphy, Zac Oyama and Siobhan Thompson) and dungeon master Brennan Lee Mulligan have played their “Fantasy High” characters in two sequel seasons (“Sophomore Year” and “Junior Year”) but “Dimension 20: Battle at the Bowl” assembled the so-called “Bad Kids” to take down an infamous villain from their past.

“I never thought Chungledown Bim would reach into the bowels of my own life,” Wilson admits. “I worked at the Hollywood Bowl for two seasons when I was in high school, and now, for some reason, I’m doing battle with him there. It’s beautiful how something as small and fun as one interesting NPC that Brennan Lee Mulligan creates has been able to bring on this richness and this creature that has truly haunted me for years.”

While the longevity of “Fantasy High” allows Wilson to continue finding new layers to a PC he created more than six years ago, he says there’s always a magic to creating a new character in a new world.

“There’s also something just as exciting for us about being new people, creating new characters that are more reflective of where we are in our lives,” Wilson said. “I’m the oldest I’ve ever been when I created a character for a ‘D20’ season, and this is the oldest character I’ve ever played. It’s fun to bring all the new skills and confidence that we have in this art form that we didn’t have when we started to new characters and new energies. It’s a really fun place to start.”

Wilson’s new character in “Cloudward, Ho!” is adventurer-turned-author Montgomery “Monty” LaMontgommery, a now-retired ranger who parlayed his adventuring days into a career as a dime novel author.

“I was really excited when Brennan [Lee Mulligan] hit us with this premise and the idea of this gang, these adventurers that get back together,” Wilson said. “I really wanted to play someone who had been an adventurer and an excited person in their youth, who then kind of manicured and changed and shaped themselves to be a more presentable version of that person.”

With his commanding presence and wisened solemnity, Monty LaMontgommery is a far cry from Fabian Seacaster, the foppish, entitled half-elf Wilson is most known for playing in “Dimension 20.” According to Wilson, Monty’s voice and personality are inspired by another adventurer-turned-author: President Theodore Roosevelt.

“I honestly based a lot of the elements of the backstory and the mannerisms around Teddy Roosevelt. I went back and watched a PBS documentary about him and his life, and there is this really interesting thing of ‘What does it mean to be wild?’”

“What does it mean to have lived a life where you’re communing with a moose?” Wilson wonders. “You’re someone who’s truly of nature, and then you shape yourself into someone who can be in spaces where decisions are being made. I wanted an old soul, but with a little bit of roughness, a little bit of edge that’s still there. Especially when his friends come and find him, I wanted that roughness to be unleashed.”

Monty marks the second time Wilson has played an author on “Dimension 20:” in “A Court of Fae and Flowers” his character Lord Squak Airavis was revealed to have a secret, flourishing career as an author under the pen name “Airry Pearry.“

“Authorship is a fun thing to play,” Wilson said. “I think for Squak, it was a little bit more of something that was discovered at the table. ‘Oh, turns out I wrote these books and turns out they’re smash hits.’ That’s the beauty of D&D and actual play, to have the ability for something that isn’t planned become central to your character, and to find ways to support that and be supported.” 

While Airry Pearry remained mostly in the realm of recurring gag, Wilson says Monty’s authorship was always a key part of his character, and one made more interesting by an offhand joke from Brian Murphy’s “Cloudward, Ho!” character, Maxwell.

“For Monty, I wanted this character to be a folk hero and someone that people knew of, someone who had great legends about him,” Wilson said. “The way Brennan and I settled on doing that was that he’s an author of his dime store novels in which he’s the central character, kind of like a Buffalo Bill type in this cloud, steampunk era. The idea of somebody paying a dime for a paperback that chronicles their adventures, I think Murph just made a really incisive decision to be like, ‘I don’t like the back half.’”

Though Maxwell’s disdain for Monty’s books is mostly a product of playful antagonism between Murphy and Wilson in real life, the early moment of improvisation ended up becoming a foundational part of Monty’s character.

“I guess there’s a core element to these stories that Maxwell likes, but eventually Monty falls off,” Wilson said. “I think we find a really interesting way to integrate that into the heart of the characters. That’s why I love actual play, Murph giving me that gift allowed me to spin it into, ‘Well, why did those books fall off? Why did those books feel different? What was going on in Montgomery’s life as they changed?’”

Neither Wilson nor any of the other Intrepid Heroes have entered the dome as a Dungeon Master, but he says he has ideas for running a campaign with usual DM Mulligan and his “D20” castmates as the players.

“I do. Right now, I’m working with Brennan, Aabriya Iyengar and Erika [Ishii] on ‘Worlds Beyond Number,’ and I’ll be DM’ing there in the near future. But that core group of the Intrepid Heroes has my heart in such a way, that I think a side quest in one of those existing worlds with that group of people would be really fun.”

“And I think it’d be fun to terrorize Brennan the way he has terrorized me,” he adds. “That’s not just something I’m saying, that is a promise that, should I ever be in that chair, I’ll make Brennan’s life a living hell, because he has lovingly made mine one as well.”