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Imaginary heroes for hire

In the game, they are grizzled warriors, holy zealots, cut-throat assassins and dangerous pirates. Outside the game they are voice-over artists, tap dancers, musicians, comedians, teachers, martial artists and private investigators. This is the story of Chaotic Amateurs, a podcast that records the transformation of four Salemites into dwarves, elves and Hobbits. Since 2016, the podcast has been publishing weekly episodes of them playing Dungeons and Dragons in an ongoing story.

One of the maps Chaotic Amateurs has drawn up for their imaginary world. Photo by Bentley Michaels

Dungeons and Dragons (D&D) is a pen-and-paper role playing game created in 1974 by Gary Gygax and Dave Arneson. The game usually has about 2 to 6 players who act as their own characters in a medieval fantasy world. One player chooses to be the Dungeon Master (DM), and they narrate, role-play as the characters with which other players interact, and act as a referee for the players. The role-playing game also requires an assortment of oddball dice: the twenty-sided die, the eight-sided die, the four-sided die and others. Unlike other games, D&D is mostly played in the theater of the mind: anything can happen, the only restriction is what the DM wants to allow to occur or not.

The DM for Chaotic Amateurs is Bentley Michaels, voice-over artist, tap-dancer and local comedian. He guides his players through a world that he and another player made specifically for the game. Rett Weissenfels, private investigator and drummer, plays the gruff dwarf warrior Durok Dragonsbane. Dash Thompson, stand up comedian, plays the crazed elf-pirate-wizard Paelias Ianerth. Milo Frasier, former member of The Courier and Chemeketa tutor, plays the pious Hobbit Ren Lifesoil and Caleb Hood, martial arts instructor, plays the inquisitive Jamhorn Dorril. In the game, they use their skills to fight monsters and solve puzzles, outside the game they use their skills to publish their weekly adventures.

DM Bentley’s notes. Photo by Bentley Michaels

Chaotic Amateurs initially started as the brainchild of Caleb Hood and Bentley Michaels in 2016. “I didn’t play,” Michaels said. “I had never played before. I was like, ‘you make some guy or gnome and make some silly voice and just mess around?’ I’m nerdy about tap dancing and like voice-over actors and drummers, I don’t know anything about Dungeons and Dragons.” Hood asked Michaels to listen to the D&D podcast Sneak Attack. “After a couple of days, I say ‘This podcast is pretty badass.’ [Hood] goes ‘You wanna start a podcast with me—a D&D podcast?’ ‘You’re goddamn right I do,’” Michaels said.

This was not Michaels’ first foray into podcasting. He ran The 45th Parallel, a podcast about paranormal legends. Neither Hood nor Michaels had much D&D experience when it first started, so they wanted to find people who knew what they were doing. “I kind of put feelers out to some people and Rett [Weissenfels] was one of them.” Michaels said, “I was like ‘Have you ever done Dungeons and Dragons before?’ ‘Oh yeah, man! Totally.’ I was like, ‘Caleb and I are thinking of putting together a team and making a podcast. You seem like you know a lot, do you want to be the DM?’ Solely based on a couple text messages.” The podcast eventually took in Weissenfels as their DM for their first season.

Another of the maps Chaotic Amateurs has drawn up for their imaginary world. Photo by Bentley Michaels

“That first season though was a lot of fun and I actually have a lot of good memories from it. My primary passion in life is writing, so I just get to write these fun stories and adventures,” said Weissenfels. Since starting the podcast and they have had a consistent viewer base. “We have a lot of longtime listeners. People who have been with us since episode one. It’s funny because we were just talking on twitter with this girl who literally tuned in on episode one and has been with us ever since,” Weissenfels said.

After some turbulent changes in the personal lives of the members of Chaotic Amateurs, Bentley Michaels became the new DM for Season Two. “Bentley was like ‘Hey man, I want to take a shot DMing this thing. What do you think?’ I was like ‘We’re Chaotic Amateurs, bitch,’’ Weissenfels said. Michaels has been DMing the game for the last two seasons.

Dragonbane familial crest that the DM made for Weisenfels’ character, Durok Dragonsbane. Photo by Bentley Michaels

Michaels uses his voice talents to act as anything from elves with high falsetto voices to dwarves with low growling voices. Since taking over, he has been in charge of writing the world and adventures the group can interact with. Being that D&D is very improvisational in nature, everything doesn’t always go according to what Michaels has written. He has to balance the spotlight of his story between these very bombastic characters. Frasier said, “I think a big thing with D&D is finding a moment for each person’s character. Where they can explore who they are and progress their story.”

Their adventuring party, nicknamed Ren and Friends, have explored dwarven ruins, fought countless foul beasts, spoken with a god, sailed pirate ships, and time traveled, all without ever having to set foot outside. Using D&D as a medium, Chaotic Amateurs manages to make their own unique brand of collaborative storytelling.

Episodes of Chaotic Amateurs can be found on, Apple Podcasts, Stitcher, Player FM and wherever podcasts can be found.

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