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This Toronto man plays Dungeons & Dragons for a living

John Dempsey was in a career crisis until he turned his life's obsession in Dungeons & Dragons into a job.
John Dempsey, Dungeon Master for Hire, has no trouble getting into character. (Cathy Irving)
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This documentary first aired in October 2017.

By Pete Morey

When I first met John Dempsey, he was about to gamble his future on a career as a professional 21st century "Dungeon Master for Hire." But John's passion for the game Dungeons & Dragons (or D&D) goes way back.

John was the new kid in his Grade 9 class. He was lonely. His teacher noticed, and decided to give him a game. She thought it would help him make friends… which it did, and so much more. Dungeons & Dragons changed his life.

Dempsey
Dungeons and Dragons Player's Handbook (Pete Morey)
It was an early edition of D&D, the fantasy, tabletop role-playing game. In the game, players create characters in a medieval fantasy world where magic is real, and dragons really exist. You can play a human, an elf, a dwarf or one of many other races. Like in the real world, in D&D you need a job. You might choose to be a wizard, a thief or barbarian, among others.  

A Dungeon Master (or DM) is the person who runs the game. They are the storyteller, describing to the players what they see and hear. The DM also plays the part of all the monsters.

Fighting a giant, in Dungeons and Dragons (Pete Morey)

John was the DM for his group of friends in Orangeville.  

When they were first getting into the game, the town had just gone through a grisly double murder. People connected the crime to D&D, stigmatizing the game. This made accessing D&D manuals or organizing gaming groups difficult.  

But John's group persisted, playing together for years, until everyone starting growing up, getting married and having kids. John took a break from D&D. He became a father to three daughters. He worked as a furniture removal guy, and he trained as a martial artist and Shiatsu therapist. He tried to make ends meet. But he was down on his luck. Life went on, but his desire to play never went away.

Dempsey

Last year, John turned 45. He was still addicted to Dungeons & Dragons. During the summer, facing a mounting pile of bills, John had an idea. What if he could turn his hobby into a job? On an impulse, he decided to try making money using his deep knowledge, skill and impressive collection of D&D paraphrenalia as a "Dungeon Master for Hire."

John Dempsey, Dungeon Master for Hire (Cathy Irving)
He placed an ad online. After one month with no responses, he was ready to give up. Then he had a strange stroke of luck. The first group who paid to play with John were a production company that made music videos. They had so much fun in John's dungeon that they were inspired to make a D&D-themed music video for the Toronto band BadBadNotGood. They hired John as a consultant and even worked him into the video for the song "Lavender," giving his website free promotion. After almost 300,000 people saw the video, business started to pick up.

Then John got another break. Around the same time his business began to ramp up, streaming giant Netflix debuted the show Stranger Things. Set in the 1980s, a peak period for role-playing games, the show borrows the style and feel of that decade's best horror and fantasy shows.

Noah Schnapp, FInn Wolfhard, Gaten Matarazzo, Caleb Mclaughlin star in the Netflix series Stranger Things (Netflix)
In the opening scene of the first episode, four boys are playing D&D in the basement, deeply immersed in the game. That was all it took. After watching Stranger Things, a whole generation of millennial Canadians who'd never thought about role-playing games got out their phones and started Googling. And some of them found John, ready and waiting to lead them on an adventure. He claims to be the only person in Canada offering this strange service. Many have braved his Dungeon Challenge.
Dempsey
A year after he came up with the idea, John has turned his obsession with D&D into his dream job. He has made fantasy his reality. He just hopes he can keep it going.
Father and daughter, John and Xena Dempsey (Pete Morey)
And maybe one day he can pass the business onto Xena, his youngest daughter and the game's newest convert.
Xena Dempsey, on her career aspirations

Meet the real-life D&D players in John's dungeon

This group of friends found John on Kijiji after watching Stranger Things. They meet up and play once a month. In real life they work construction, design and office jobs, but once they enter John's dungeon, they are "Danger Force."

"Perry the Black", aka Michael (Pete Morey)
Real Name: Michael

Character Name: Perry the Black

Race: Human

Class: Sorcerer

Alignment: Neutral Good

Level: 6

The weird thing is when you look online for a dungeon master you kind of think you'd get creepy things. But we found him and it all worked out great.- Michael/Perry the Black
Robert "the Robe" Sulanov, aka Robert (Pete Morey)

Real Name: Robert

Character Name: Robert 'The Robe' Sulanov

Race: Half-Elf

Class: Rogue

Alignment: Neutral Good

Level: 7

I'm going to run and jump off the edge of the coffin and plunge both my silver sword and my dagger into its back.- Robert/The Robe

"Lyder the Ranger", aka Dale (Pete Morey)

Real Name: Dale

Character Name: Lyder

Race: Human

Class: Ranger

Alignment: Lawful Good

Level: 5

Lyder

"Zanna Garrick" aka Julio (Pete Morey)

Real Name: Julio

Character Name: Zanna Garrick

Race: Elf

Class: Mystic

Alignment: Chaotic Good

Level: 4

Zanna Garrick
"Ricky the White" aka Mark (Pete Morey)
Real Name: Mark

Character Name: Ricky the White

Race: Human

Class: Paladin

Alignment: Neutral Good

Level: 5

And I just scream in righteous voice, 'If you think this is funny, you have no idea who just walked in here.'- Mark/Ricky the White
"Varia" aka Ashleigh
Ashleigh McEwan was raised in an analog age, but went to work as an advertising exec in a digital age. After six months playing the game, she finds Dungeons & Dragons a unique escape in our technology-driven world.

Real Name: Ashleigh

Character Name: Varia Papholopolus

Race: Human Thyatian

Class: Sage

Alignment: Neutral Chaotic

Level: 6

Varia walks into the bar, and she is stunning. Everyone looks at her in the entire room', and that sort of set the stage for my character's loose morals."- Ashleigh/Varia
"Citara Greenbottle" aka Xena (Pete Morey)

The youngest and most fearless adventurer in John's Dungeon is his 10-year-old daughter, Xena. She has been slaying giants, fighting spiders and looking for treasure since she was nine.

Real Name: Xena Dempsey

Character Name: Citara Greenbottle

Race: Halfling

Class: Rogue

Alignment: Neutral Good

Level: 4

John Dempsey, Dungeon Master for Hire. (Cathy Irving)
Rurik my friend and I was hugging him and then it wore off and I got this dirty dwarf beard in my face."- Xena Dempsey/Citara GreenBottle (age 10)

Producer Pete Morey
About the Producer

Pete Morey is the producer of Marvin's Room & Afterdark on CBC Music. He started at CBC Radio in 2006, and has since then worked on and hosted too many shows to list here. In his spare time he enjoys music, comic books, spectacles (as in eyewear, he's English), bicycles and baseball. He plays a mean ukulele, has a gentlemen's book club and once trained as a professional clown halfway up a mountain.

For this documentary, he was a level 5, true neutral, half-elf thief called Carric Liadon until he died in John's dungeon.

You can friend him, follow him, or tumble with him if you so choose.

Find Pete Morey online at:

cbcpetemorey.tumblr.com

facebook.com/Cbcpetemorey

@cbcpetemorey

This documentary was made through the Doc Project Mentorship Program.

Thanks to Cathy Irving for her playful photography.

Thanks to ambient-mixer.com for these two Creative Commons Sampling Plus 1.0 License audio soundscapes that were featured during the game: Dennis Dungeon and D&D Fantasy Inn Pub Tavern.

The Stranger Things theme music is composed by Kyle Dixon and Michael Stein and distributed by Sony Music Canada.