Artists on ‘Critical Role’ and ‘D20’ Say How They Got Their Dream Jobs | Invesloan.com

• Critical Role and Dimension 20 are nerdworld cornerstones.
• Artists like Cait May, Eren Angiolini, and Hannah Friederichs create art for the crews.
• They talked with BI about what goes on behind the scenes and how they got their gigs.

The people behind breakout nerdworld hit shows “Critical Role” and “Dimension 20” have found a way to turn streaming themselves playing tabletop games like “Dungeons & Dragons” into lucrative business ventures.

In 2025, both teams are scheduled to play sold-out live gigs in arenas and theaters across the US. The eight members of CR are also embarking on a 10th-anniversary global tour, which will include arenas in Australia.

The cast members are the most recognizable part of the enterprises, from big-name game masters like Matt Mercer and Brennan Lee Mulligan to CR’s heartbreak prince, Liam O’Brien. But behind the scenes, there are crew members and artists helping make the shows shine.

Business Insider spoke to three full-time artists who’ve worked on projects for CR and D20: Cait May, Eren Angiolini, and Hannah Friederichs. They have made a range of illustrations, from fan-favorite character designs to comic book iterations of CR stories.

Behind the scenes at CR and D20

People who watch the shows may recognize Friederichs’ art from CR series like “Exandria Unlimited” and, more recently, the team’s third, long-running “D&D” campaign, “Bells Hells.”

May’s work, meanwhile, can be seen on Dimension 20. Her art is in episodes of “Fantasy High: Junior Year” and “Never Stop Blowing Up.”

Angiolini’s art is featured in CR’s comic books, released by Dark Horse Comics.

Friederichs told BI that she was initially commissioned to work on CR’s “Uk’otoa” board game, then brought back to make character art for O’Brien’s character, Orym.

“I sent in five or six pages of concepts and went down a rabbit hole researching swords. I was like, ‘This one’s got a leaf blade, this one’s got a straight blade, this one has a tapered blade,'” Friederichs said of her interview process. “I went completely overboard, but it worked out, and Liam liked it.”

Sheet metal and lightning

There’s no fixed road map to getting a gig with CR and D20, but each of the artists BI spoke to had tips for those who’d like to get in on the action.

Friederichs said a piece of art she made for her husband helped her clinch her first gig with CR.

“My husband wanted a playmat for ‘Magic: The Gathering.’ I drew one with boats on it, and that’s what got me hired for ‘Uk’otoa,'” Friederichs said.

“My tip is: just do your best work,” Friederichs added. “Whenever I’ve gone to portfolio reviews, none of that advice has actually gotten me a job in the industry, but doing that one piece for my husband did.”

May told BI that publishing as much of her art as possible and networking within the fandom helped her early in her art career.

“Opportunity is like getting struck by lightning,” May told BI. “It may never happen. But there’s nothing stopping you from dragging a bunch of sheet metal out into an open field to increase your chances.”

Fan art is fair game

Angiolini told BI that drawing fan art is one way to get noticed. Angiolini remains an avid CR fan artist and still posts CR fan art on their social media.

May added that if artists have ideas on how characters could look, they could always create their own reimagined takes on the character art and post them online.

“Make something that is really cool. It could get you noticed, and maybe you’ll get to make the official stuff, too,” May said.

Working fast

May says her projects at D20 involved quick turnarounds and intense bursts of work. The workflow was similar to regular commissions, where she sent in sketches that she later colored and rendered.

“The pipeline becomes very different when you’re making something that needs to be then altered or put into the editing,” May told BI. “That was a learning curve for me.”

May said that on one seven-month-long project for D20, she made art for 75 characters and background projections. She also got to see all the uncut footage D20 had filmed.

“I was working as fast as I could with the backgrounds while playing footage of the show they shot the day before,” May said.

Angiolini said that CR’s cast and editors try to get notes for the comics in as early as possible.

“I think Liam and Sam had a couple of extremely minor notes,” they said of CR co-founders O’Brien and Sam Riegel. “When I met them sometime after, they were like, ‘Oh my god, we’re so sorry about the notes.’ I was like — ‘You’re fine, you’re good!'”

Angiolini also had to turn a character commission around for CR in two weeks so they could make their deadline for CR’s “The Mighty Nein Reunion — Echoes of the Solstice” live show in London. They said the project went well, even with the tight timeline, because they received a succinct creative brief from which to work.

“I sent them three iterations with slightly different variations to choose from,” they said.

The artists told BI that working with CR and D20 still feels like working with fellow nerds who understand the process and see the value in paying for art — instead of generating things via AI.

“It’s because they get it. They aren’t a giant conglomerate — they’re making something creative too, and want people to be a part of it,” May said of D20.

Angiolini said that while working with CR, they felt the team genuinely understood how freelance artists struggle to stay afloat — and why it’s important to pay people well.

“The fact that they strive to include marginalized voices in the community and make space for them — I think that’s really admirable too,” Angiolini said.