For Caldwell Tanner (’09), the enduring memories from his four years as a member of Wake Forest’s Lilting Banshees comedy troupe don’t involve a favorite quirky character or show-stopping scene. It’s the late nights he spent with fellow troupe members, putting in the work to build sketches.

Caldwell Tanner (’09) at his job as CollegeHumor’s editorial illustrator; and in the top photo (far right) performing “Not Another D&D Podcast” live. Photos courtesy of Tanner

During those sessions, he learned there are far more ways to be funny than simply being wildly personable or charismatic; the best laughs come from working together. “It was more about the exercise and the joy of writing and messing around with your friends,” he says.

That joy of messing around with friends guides Tanner now in a successful comedy career that’s moved from digital publications to television before taking a seemingly unconventional turn to the fantasy tabletop role-playing game Dungeons & Dragons. 

Today, Tanner is one of four performers featured on the hugely popular “Not Another D&D Podcast,” now in its sixth year. Tanner credits his success with being a lucky guy who has a bunch of funny friends. “I love collaborating,” he says. “I like making things with other people, and I like lending and blending my voice with others.”

Lilting Banshees alum Mike Baireuther (’08), a longtime friend, says Tanner should give himself more credit. “Caldwell does something in comedy that’s very hard to do, which is that he can be equally very silly and smart at the same time,” Baireuther says. 

Wake to CollegeHumor pipeline

At his Nashville, Tennessee, high school, Tanner dabbled in improv and penned a comic strip for his school newspaper. “I always wanted to be a newspaper cartoonist, but I was one of those people that was born, perhaps, a generation too late for that to be a totally viable career,” he says. 

By the time he got to Wake Forest, drawing and comedy were still favorite activities. He landed a spot on the Lilting Banshees, eventually becoming its director, and a comic strip in the Old Gold & Black.

“He is a rare mix of someone who is both incredibly talented and funny, but also very gracious and a wonderful listener, which makes him kind of the ideal collaborator,” says Baireuther, who also shared a comedy and music show on Wake Radio with Tanner. “When I was (the Lilting Banshees) director, it was always hard because everyone wanted to write their sketches with Caldwell because if a sketch wasn’t going well, there was a feeling that Caldwell will fix it.”

As Tanner set his sights on a professional career, however, he attempted a more traditional path. He originally planned to major in business until he earned his lowest grade ever in a required discrete mathematics class that steeped him in the study of mathematical structures dealing with distinct values. He had to beg the teacher to give him a “merciful C-minus,” he jokes. 

Tanner dropped the business major and, as a student enamored with technology, including his University-issued laptop, eventually decided to major in art. He installed Photoshop on that laptop and began drawing digitally on a small tablet he bought on his own.

“While learning digital art, I taught myself a little bit better how to draw digitally and how to basically use digital media,” he says. “And I tried to shoehorn that into everything I did for the next four years at school.” 

By his junior year, he nabbed an internship with CollegeHumor, thanks, in part, to Wake Forest and Lilting Banshees connections. The comedy site was co-founded by former Lilting Banshees members Ricky Van Veen (’03). Another Lilting Banshees alum and CollegeHumor writer Sarah Schneider (’05), who later became a writer for Saturday Night Live and co-creator of the Comedy Central sitcom “The Other Two,” hooked Tanner up with the internship.

Tanner spent the summer in New York, writing, drawing and supporting video production for the site. Back at Wake Forest, he continued to freelance for the platform. “I’d always been interested in a variety of disciplines under comedy, and this showed me … (that) I can write; I can draw; I can make videos,” he says. “It really felt like this is something I can work towards.” 

Storyboarding at Disney

About a year after graduating, Tanner landed a full-time job at CollegeHumor, which has since gone through ownership changes and is now called Dropout. For the next six years, he worked for the multimedia comedy site, writing, drawing, creating videos and voice acting. 

“Dinosaur Office” was one of the bigger series in which he was involved. Tanner and three colleagues created the stop motion show, which was released on Nintendo 3DS. It tells the story of “what kids think their parents do at work through the lens of playing with dinosaur toys,” Tanner says. 

Along the way, he also was stretching his animation skills. He wrote a couple of episodes for the Cartoon Network show, “Teen Titans Go!” And in 2016, he jumped from CollegeHumor to the Disney Channel to work on the hit animated series and movie “Big City Greens.” He’d originally applied to be a writer on the show. But when colleagues learned he could draw, they asked him to reapply as a storyboard artist, who would create a visual script for the show. He got the job — a dream come true.

“Storyboarding is kind of like the amalgamation of all the things I had been learning over the years,” Tanner says. “This was a perfect fusion of all those skills.”  

A radio drama with dice

What happened next was mostly a cascade of connections and coincidences. While still at Disney, Tanner joined two CollegeHumor and Dinosaur Office alums — husband-and-wife duo Brian Murphy and Emily Axford — on their “8-Bit Book Club” podcast, which featured the readings of video game novelizations.

In one episode, the group played a little Dungeons & Dragons. Murphy and Axford already were regular players, but Tanner had only played a handful of times. The episode was popular, and the rest is history. Jake Hurwitz, another comedy writer and CollegeHumor alum, joined with the three to create “Not Another D&D Podcast.”

Tanner eventually left Disney in March 2020 to work on the podcast full time, a move that gave him some modicum of a work-life balance, says Susanna Wolff, his wife and fellow CollegeHumor alum and comedy writer. The couple have a young daughter and another child due in December. “(Caldwell’s) extremely genuine, and his biggest flaw is probably people pleasing,” she says.

Today, the podcast has a significant following with 1.5 to 2 million downloads a month; a Patreon fan base of about 46,000 people who pay to subscribe and get special perks; and live, in-person shows, on occasion, that pack in fans. Some episodes of the podcast revolve around the drama on other people’s D&D tables or “8-Bit Book Club” discussions.

But, most often, the episodes cover the game play of Tanner and his collaborators. D&D involves players creating their own characters, navigating various adventures in a fantasy world and rolling dice to determine actions and outcomes. A Dungeon Master guides the game.

“I like to describe (episodes) as essentially, just like a radio drama, but with dice rolling added in,” Tanner says. “We follow the rules of D&D. But (Murphy), as the (Dungeon Master), narrates what’s happening. we edit, then add sound design and music, which is all done by our incredible co-host Emily. … We just treat it like it’s an audio book or an audio drama, but we don’t know where it’s going, because the dice are controlling what happens.” 

So far, the four have embarked on several different campaigns, each with their own characters and narrative arcs. In the first campaign, Tanner played the role of a “halfling” Boy Scout named Beverly ToeGold V, a character pulled from Caldwell’s real-life experiences. It was a good way to learn the game, he says.

Starring in a D&D podcast was not in Tanner’s original career plans. But just as with the Lilting Banshees, CollegeHumor or “Big City Greens,” Tanner simply found another opportunity to work collaboratively with other funny people for a laugh. And that’s always been his goal. 

“It’s certainly a left turn,” Tanner says. “But, going back and thinking about where I started with comedy, like in college and before, it doesn’t feel like that much of a shock, because the core of it is just hanging out with your friends and trying to make something funny together.” 

Sarah Lindenfeld Hall is a longtime North Carolina-based journalist, former staff writer for the Winston-Salem Journal and The (Raleigh) News & Observer and founding editor of WRAL-TV’s popular parenting website. Today, she’s a freelance writer, regularly diving into stories about interesting people and parenting, health, education, business and technology topics.