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Dungeons & Dragons is like a big ol’ nerd umbrella wide enough accommodate many types of players. Do you like roleplaying colorful characters? Do you enjoy rolling dice, crunching numbers, maxing out damage? Do you have an epic world brewing in your head? You’re all covered. Additionally, the game’s focus on shared storytelling especially attracts creative people, from writers and illustrators to musicians and actors. That got us wondering how classic authors would play Dungeons & Dragons if they were alive today. Grab your D20 and let’s go!

 

William Shakespeare

The Bard of Avon would be the first at the table and the last to leave. Don’t forget he was an actor too, so he’d savor every chance to perform in-character. Yeah, Bill would be the player who talks to every NPC for at least ten minutes, exclusively in iambic pentameter, while making the dungeon master scramble to improvise. We also see him performing a monologue with every spell, much to his party’s chagrin. They’d complain, sure, but we doubt he’d get kicked out since every group needs a healer. Shall I compare thee to a scroll of cure wounds…?

Character race and class: Human bard (duh).

Most prized inventory item: A potion of false death he’s afraid to use because it may be too convincing.

 

Edgar Allen Poe

The most famous emo boy in all of literature would love the gothic details of Dungeons & Dragons, especially the Ravenloft campaign setting. We see Poe as the party’s heel, counterbalancing Shakespeare’s flowery language with acerbic one-liners—he was a famously caustic literary critic after all. On adventures, Poe would be the player who stops the party every ten seconds to roll investigation checks. Random skeleton? Need to examine for cause of death. Haunted castle on the hill above the village? Need to roll for clues about the architecture. Odd section of wall in a dungeon? Need to check if somebody’s entombed behind it.

Character race and class: Tiefling warlock who made an eldritch pact with an ancient god.

Most prized inventory item: His familiar, a raven named “Poe Money, Poe Problems.”

 

Ernest Hemingway

Hemingway is famous for his larger-than-life hobbies, so he’d be drawn to the epic adventures that can only happen in a pen and paper game. No doubt he’d be the first to set off on a dangerous treasure hunt or lead the defense of an innocent village. We see him as the party’s leader, the one who’d wax poetic about bravery and the nature of war before important battles (in simple sentences, of course). He would definitely be that one player who gets drunk at every inn the party visits. Those charisma checks are only getting harder, Ernest.

Character race and class: Half-orc fighter who accidentally invents boxing gloves by wrapping his hands in Shakespeare’s old leather armor.

Most prized inventory item: The skull of a displacer beast he killed on an extraplanar safari and mounted above his fireplace.

 

Hunter S. Thompson

If Thompson’s manic first-person style is any indicator, he’d go wild with the game’s improvisational freedom. He’d be the player throwing curveballs at the party, like eating a magic flower to get high instead of using it to defeat the evil forest witch. His famous anti-authority streak would land him in real trouble, though. If he didn’t lash out at the baron ordering the party to rescue kidnapped villagers, he’d argue with the dungeon master after every roll. Let’s be real. Any session with Thompson would probably end with the entire party either arrested or dead.

Character race and class: Half-elf sorcerer with abnormally high constitution to combat the frequent hangovers.

Most prized inventory item: That magic flower. Seriously. A dying arch fey bequeathed it to him and now he’s saving it for when he wants to get very, very intoxicated.

 

Jane Austen

If anyone knows how to navigate a group of improvisers and nerds, it’s Jane Austen. That’s why we’re convinced she’d be the dungeon master. Austen would exercise total control of the table, keeping a close eye on her players’ quirks to stay one step ahead. Using her NPCs, she’d subtly pit players against each other for maximum drama and entertainment. Knowing Austen, her favorite challenges would be social, like forcing her ragtag party to infiltrate a nobleman’s fancy dinner party. They’d have to fake their way through discussions on high art and sensibility to steal a magical macguffin.

Her campaign’s big bad evil guy: A very wealthy (and single!) black dragon.

Her favorite way to spice up a battle: Hopping on the pianoforte and laying down some tense tunes.


Quirk Tested. Reader Approved.