Jesters of Ravenloft: A D&D Podcast

Jesters of Ravenloft: A D&D Podcast

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!

Episodes

October 4, 2025 45 mins

Gandalf the Grey delivered a message through a moth, saying he was imprisoned and that whoever heard his message must help Yolo flee to Rivendell immediately, so the troupe tried to do just that. Jimothy McGristle made his last stand at the front door of his pub as the troupe escaped out the back only to face a whole town looking for hobbits. Yolo put the ring on to hide, and Guy picked up Frodo and began to whisk him away...

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The troupe continued to search for Gandalf, but found themselves in an increasingly hostile town. Del remained at Jimothy McGristle’s to watch the hobbits, Guy tried to convince the guard at the gate that the hobbits had left town, Adam learned that there was a huge bounty on the hobbits’ heads, and Tyler overheard someone revealing where the hobbits were being sheltered before her voice was abruptly cut off. But when Tyle...

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September 26, 2025 54 mins

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 Everet...

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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-tu...

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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 th...

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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...

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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 ...

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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 ...

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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 ringbea...

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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 calle...

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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...

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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 ...

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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 f...

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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 h...

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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 th...

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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 ...

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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 replaceme...

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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 Bombad...

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Comedy troupe Wet Change met their strange Santa-like saviour, Tom Bombadil, who invited them to his home before vanishing in a puff of butterflies. Before heading out, the troupe scoured the crypt for loot and took stock of their fighting experience. Guy knew some taekwondo, Adam knew some karate, Del took a semester of archery, and Tyler found a locket that made him feel a bit safer. Del used her phone’s compass to direc...

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The sketch comedy troupe, Wet Change, was performing at Edinburgh Fringe when suddenly they were engulfed by mist. They emerged from the foggy swirl of leaves onto a forest road. They soon met a friendly and welcoming merchant, who was immediately slain by a terrifying cloaked figure on horseback. Del, Tyler, Adam, and Guy fled through the woods and sought shelter inside a crypt, only to find it was already occupied by a m...

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