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PODCAST

Jesters of Ravenloft: A D&D Podcast

Dumb-Dumbs & Dice

Jesters of Ravenloft is a D&D 5e podcast where a group of comedians are sucked into Dungeons & Dragons - and now it"s up to them to become heroes and escape Ravenloft! A new episode drops every Friday and Saturday and, don"t worry, there are NO SPOILERS for Strahd. Ranked in the top 50 fiction podcasts on Spotify and Apple Podcasts, check out Jesters of Ravenloft and find out why it"s been downloaded more than 2M+ times now!

fiction comedy fiction

All Episodes

00:54:51

Canada By Night - 1.02 - The Situation

Jesters of Ravenloft: A D&D Podcast ·

2025/09/26

Continuing the story of Canada By Night, a Vampire: The Masquerade live-play podcast, Everett Fry was sent to Calgary to save his friend’s mother, but after arriving in the town of New Haven, he was immediately thrust into the role of sheriff. Deputies Doris, Val and Evangeline arrived at the station only to find themselves defending it against four frenzying Kindred. After subduing three of them, they turned to see Everett feeding on their remaining foe. What will our deputies make of their new

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00:57:02

Introducing... Canada By Night - 1.01 - Welcome to...

Jesters of Ravenloft: A D&D Podcast ·

2025/09/26

Since our Jesters were out of town this week performing at a live show, we'd like to introduce you to another Dumb-Dumbs & Dice podcast, Canada By Night, a Vampire: The Masquerade live-play podcast, featuring the familiar voices of Ryan, Tyler, and Del!Our story begins as many do, at the end of a journey—with one coterie breaking up before another can form. We’re thrown into the world of Everett Fry, a detective-turned-reluctant-vampire, who will be forced to leave Montreal to help a

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00:44:10

Jesters of Middle-earth - Episode 17 - Have You Seen...

Jesters of Ravenloft: A D&D Podcast ·

2025/09/20

The next morning, the boys spent some time assessing how bad they all smelled. The hobbits were anxious to find Gandalf, so Del stayed back to look after them, and Tyler and Yolo argued over leadership within the fellowgroup, while Guy scoped out the situation at The Prancing Pony and Adam checked at the gate for any sign of the wizard. When the gate guards heard about the hobbits, one of them took off running, but then the other shot him with an arrow, crying out about getting some reward for

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00:47:54

Jesters of Middle-earth - Episode 16 - An Elf, a...

Jesters of Ravenloft: A D&D Podcast ·

2025/09/20

The troupe settled in to try get a good night’s sleep before meeting Gandalf the next day. Del was afraid, so she slept on the floor in Tyler’s room, Tyler realized he could only sleep when he was wrapped in the dead ranger’s cloak, Guy struggled to fall asleep because his newly-acquired darkvision wouldn’t let him have total darkness, and Adam found nothing interesting about the silver tree-and-stars ring he took from the dead ranger, so he went right to sleep. The next morning, Guy’s hair was

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00:48:45

Jesters of Middle-earth - Episode 15 - The...

Jesters of Ravenloft: A D&D Podcast ·

2025/09/13

Having escaped the mayhem at The Prancing Pony, Adam and Guy took the dead elf into an alley to loot him, and Del, Tyler, and the hobbits joined them to plan their next move. The surrounding area was overrun by a mob of people, some trying to douse the fire at the inn, and others clearly still searching for the ring bearer, so they decided to take refuge at a different inn, and found themselves at Jimothy McGristle’s. Del relayed her solo journey to the rest of the troupe, and they were all left

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00:50:42

Jesters of Middle-earth - Episode 14 - At the Sign of...

Jesters of Ravenloft: A D&D Podcast ·

2025/09/12

With Walker down and the troupe out of immediate danger, Guy respectfully looted the elf who died for him, and Adam disrespectfully looted the ranger. The troupe learned that the two hobbits were the ringbearer, Yolo Took, and his butler, Frodo Baggins, but they needed to hide until they could meet up with Gandalf the following night. So, Del, Tyler, and the hobbits snuck out an upper-floor window, and Adam and Guy pulled a Weekend at Bernie's to get the elf’s body outside to loot it more

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00:43:24

Jesters of Middle-earth - Episode 13 - That Guy from...

Jesters of Ravenloft: A D&D Podcast ·

2025/09/06

The troupe was locked in combat with Walker, the ranger, while the other bar patrons seemed set on finding the hobbit and collecting the bounty. The elf who had approached Guy earlier came to Guy’s defense, but was run through by Walker’s sword, Adam convinced Snoopwise to join in the fray, but he too was swiftly taken out, and Tyler used the mysterious locket to bring Del back from the brink. Amidst the chaos, the ringbearer disappeared, but Tyler managed to protect the other hobbit from the

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00:47:48

Jesters of Middle-earth - Episode 12 - A Cloak of...

Jesters of Ravenloft: A D&D Podcast ·

2025/09/05

Off on her own side-quest, Del confronted the threatening figure and discovered it was the ranger she’d been seeking. Del dubbed the ranger “Walker” and they headed towards Bree, but were soon set upon by wargs. Walker was badly hurt, so Del patched him up and they finally arrived at The Prancing Pony inn. They quickly spotted Adam and Guy, but for reasons unknown, Walker immediately moved to attack them and when Del called out to her friends, he turned on her too. Tyler rushed downstairs to see a

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00:48:16

Introducing… The Mythos Mysteries - 1.02 - A Stranger...

Jesters of Ravenloft: A D&D Podcast ·

2025/08/29

While our dear DM is out sick, please enjoy another one of our spooky-silly shows, the completed series “The Mythos Mysteries.”The Mythos Mysteries is a Dumb-Dumbs & Dice live-play podcast where professional voice actors and improvisers delve into the madness that is the Pulp Cthulhu Roleplaying Game. Join Red, Adrian, and Old Man Richter, as childhood friends and their erstwhile mentor return home to try and save a friend! Follow our anti-heroes, and see if they can maintain their sanity

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00:50:18

Introducing… The Mythos Mysteries - 1.01 - Homeward...

Jesters of Ravenloft: A D&D Podcast ·

2025/08/29

While our dear DM is out sick, please enjoy another one of our spooky-silly shows, the completed series “The Mythos Mysteries.” The Mythos Mysteries is a Dumb-Dumbs & Dice live-play podcast where professional voice actors and improvisers delve into the madness that is the Pulp Cthulhu Roleplaying Game. Join Red, Adrian, and Old Man Richter, as childhood friends and their erstwhile mentor return home to try and save a friend! Follow our anti-heroes, and see if they can maintain their sanity

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00:47:17

Jesters of Middle-earth - Episode 11 - Walker,...

Jesters of Ravenloft: A D&D Podcast ·

2025/08/23

As Adam and Guy tried to figure out when the heck Guy had sprouted pointy ears, Hobbits with a reservation for Underhill arrived. Two rangers from across the room jumped up and one of them was Del! Earlier, at Bombadil’s house, Goldberry had told Del about a hobbit who’s supposed to destroy something but doesn’t have the protection he needs. Del was tasked with finding a ranger who can help and then follow her instincts to the hobbit. So, she departed, slightly drunk, and headed east, and eventually

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00:47:17

Jesters of Middle-earth - Episode 11 - Walker,...

Jesters of Ravenloft: A D&D Podcast ·

2025/08/23

As Adam and Guy tried to figure out when the heck Guy had sprouted pointy ears, Hobbits with a reservation for Underhill arrived. Two rangers from across the room jumped up and one of them was Del! Earlier, at Bombadil’s house, Goldberry had told Del about a hobbit who’s supposed to destroy something but doesn’t have the protection he needs. Del was tasked with finding a ranger who can help and then follow her instincts to the hobbit. So, she departed, slightly drunk, and headed east, and eventually

en

00:48:42

Jesters of Middle-earth - Episode 10 - Del and Back...

Jesters of Ravenloft: A D&D Podcast ·

2025/08/23

After they got weird shirts from Kemmet from the Forg, the troupe made their way to The Prancing Pony inn. They learned that they hobbits were expected at the inn the following night, but in the meantime, they had a show to put on. The proprietor’s introduction of Wet Change managed to turn the crowd against them before they’d even started, but they fumbled their way through some improv games and eventually won over their audience. Tyler went to bed early, but Guy was soon approached by a strange

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00:48:42

Jesters of Middle-earth - Episode 10 - Del and Back...

Jesters of Ravenloft: A D&D Podcast ·

2025/08/23

After they got weird shirts from Kemmet from the Forg, the troupe made their way to The Prancing Pony inn. They learned that they hobbits were expected at the inn the following night, but in the meantime, they had a show to put on. The proprietor’s introduction of Wet Change managed to turn the crowd against them before they’d even started, but they fumbled their way through some improv games and eventually won over their audience. Tyler went to bed early, but Guy was soon approached by a strange

en

00:50:15

Jesters of Middle-earth - Episode 9 - Improv at The...

Jesters of Ravenloft: A D&D Podcast ·

2025/08/16

The troupe approached the gate leading into Bree and unintentionally convinced the guards they were inept enough to not be a threat. Making their way through town, a server from The Prancing Pony invited them to perform at the bar in return for free accommodations, but first Adam and Guy needed proper pants. Adam found himself miraculously clad in a kilt, so they made their way to a tailor’s shop to clothe Guy. When they failed to flatter the proprietor into giving them free clothes, they instead

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00:45:08

Jesters of Middle-earth - Episode 8 - Flatter Friends

Jesters of Ravenloft: A D&D Podcast ·

2025/08/15

The troupe continued to fight the goblins. Adam failed to tame the dog-man, Guy noticed the goblins were sensitive to sunlight and set their tarp on fire to destroy their shade, and Tyler, who had run away, realized the others hadn’t followed him, so he came back to help finish things off. They then performed the unsavoury task of searching the bodies and found a crude drawing depicting hobbits and a ring, suggesting the hobbits were the targets of more than just the Black Riders. They finally made

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00:48:52

Jesters of Middle-earth - Episode 7 - A Bag of...

Jesters of Ravenloft: A D&D Podcast ·

2025/08/09

Wet Change, sans Del, set out east towards the town of Bree. They happened upon the violent willow tree, decided not to burn it down just yet, and travelled across a difficult landscape until they came across a group of goblins. Not wanting to fight, Tyler and Adam tried to run away, and Guy climbed a tree, but still they were discovered. Adam and Guy threw Baguettes and branches, but it was only the rising sun that had the strange creatures drawing back into cover. As the goblins scrambled away, a

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00:45:49

Jesters of Middle-earth - Episode 6 - Get Ready to...

Jesters of Ravenloft: A D&D Podcast ·

2025/08/08

With Del away on a mysterious adventure of her own, the rest of the troupe rested at Bombadil’s house and equipped themselves for the task ahead. Tolkien gave Tyler a broken sword, Guy had the forethought to ask for food and water, and Adam dressed himself in an improvised hat and poorly-constructed toga. The troupe departed and found themselves naturally taking on specific roles within the group: Tyler as the Guide, Adam as the resourceful Hunter, and Guy as the observant Scout. They’ve been warned

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00:44:20

Jesters of Middle-earth - Episode 5 - Bad Dreams and...

Jesters of Ravenloft: A D&D Podcast ·

2025/08/02

After Bombadil revealed himself to be J.R.R. Tolkien, Goldberry took Del aside for a private conversation, and the rest of Wet Change were left to question the author. He explained that he had often escaped into his own story, into an ethereal realm between fiction and reality, but lately the narrative had been falling apart. The heroes who usually helped the ring-bearer hadn’t shown up, so Tolkien had sought out replacements, only to accidentally bring in the self-nominated Best Ensemble, Wet

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00:51:10

Jesters of Middle-earth - Episode 4 - J.R.R. Bombadil

Jesters of Ravenloft: A D&D Podcast ·

2025/08/01

A malevolent tree put everyone except Tyler to sleep and began pulling them into its trunk! As they awoke, Guy set the branches on fire, Tyler injured himself badly getting Del free, and Del sacrificed her cell phone to wedge open the trunk just enough to grab Adam’s hand, but the tree wouldn’t let him go. So, Adam negotiated and the tree finally released him in exchange for Tyler chopping off its burning limbs. Tom Bombadil reappeared and brought them all to is house, where he revealed himself to

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