Jesters of Ravenloft: A D&D Podcast

40 Episodes
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By: 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!

Jesters of Middle-earth - Episode 44 - Was That a Dragon?
Today at 6:00 AM

The Fellowgroup arrived at the burnt, desolate landscape that used to be Lothlorien. While they battled their own dismay, they came across a charred and gored body bearing a sign that read “No safe harbours for the fellowship of the ring” and Guy recognized the figure to Celeborn, Lord of Lothlorien. They found only two elves still barely alive and learned that the destruction had happened at the hands of orcs, a fire-breathing dragon, and group called the Riders of Rohan. The headed towards the ruins of the elf sanctuary, but suddenly heard a flap of leathery wings and felt...


Jesters of Middle-earth - Episode 43 - The Desolation of Lothlorien
Yesterday at 6:00 AM

The Fellowgroup was forced to stop and rest, as GanDelf found herself getting sleepy in her newly-acquired old age, and things began to escalate with Frodo. Tyler had convinced Yolo that they should let Frodo live, Adam didn’t believe the creature to be Frodo at all, they approached Frodo to get some answers, Frodo immediately said they should kill Yolo, and Yolo took his sword and lunged at Frodo. Once things calmed down, Frodo admitted to having murdered Grungus Took, but before they could decide what to do with him, the hobbit slipped away. As they approached Lothlorien, in...


Jesters of Middle-earth - Episode 42 - The Frodo We Know
01/17/2026

The Fellowgroup fled the Mines of Moria and escaped into the open air once more. GanDelf used her newfound magic to shatter the entrance and prevent any pursuit by their enemies, and they stopped at a mirror-clear lake to heal up. Del reflected on the strange duality of both her normal self and the wizard within her, Adam waded into the strange lake to wash up, Guy tried to find drinking water that wasn’t tainted by Adam’s filth, Frodo-Gollum had a full-on conversation with himself, but no one overhead it, and Tyler found watermelons. GanDelf began leading the...


Jesters of Middle-earth - Episode 41 - I Think My Brain’s Bad
01/16/2026

Gandalf the Grey was defeated and Del found herself suddenly full of magic, having finally taken up the mantle of a fallen character. The Fellowgroup distracted the Balrog with Guy’s arrows, Del’s magic missiles, and Adam’s fiery wad of paper. With the monster preoccupied, Adam rushed across the bridge, collecting his companions along the way, and crashed into the other side of the chasm. The Balrog seemed to be gathering itself again for another attack, but as it unfurled its wings, it landed upon Tyler’s tiny Tech Deck, tripped, and fell into the abyss. Can the Fell...


Jesters of Middle-earth - Episode 40 - The Thing that Used to be Del
01/10/2026

The Fellowgroup’s fight at the bridge of Khazad-DĂ»m became more desperate as the Balrog directed the goblins and undead dwarves towards Yolo. Tyler drew his sword to entice the Balrog away from Adam, but took a brutal hit from the monster’s flaming weapon, Del helped Tyler limp away as Guy carried the hobbits across the bridge, and Adam accidentally interrupted Gandalf’s powerful spell while trying to save him. As Gandalf made his last stand against the flaming monstrosity, his final effort was interrupted by an arrow to his throat, and as the wizard turned to ash, De...


Jesters of Middle-earth - Episode 39 - Put Those Corpses Down!
01/09/2026

The Fellowgroup faced off against Durin’s Bane, the Balrog of Moria, a massive creature bearing a flaming sword and whip. They all tried to distract it, Del shooting arrows and diving under its legs, Adam trying and failing to throw dwarves at it, Denethea clashing her sword, and Guy sprinting past it. Meanwhile, Tyler picked up the frozen Yolo, and the monster seemed to have eyes for only the ring-bearer. Gandalf and Denethea got hit hard, but the wizard managed to retaliate, and the two faced off with the terror before them. But can they hold back the fo...


Jesters of Middle-earth - Episode 38 - Turtles in Time in Moria
01/02/2026

The Fellowgroup found themselves trapped in a crypt facing undead dwarves, including Balin himself! Del struggled to hit anything, Guy used his new undousable torch to set corpses on fire, Adam dealt a strong blow in his rage, and Tyler started picking up the undead and hurling them away. Yolo attempted to escape by flinging himself down a hole in the floor, and the rest of them quickly followed, falling through a massive cavern and onto a huge pile of goblin corpses. As flames approached, they fled towards the Bridge of Khazad-Dûm and the exit from the mines. B...


Wrong Holiday Episode! Jesters of Ravenloft - 2.22 - Digging Holes
12/26/2025

The troupe is locked in combat with the Gargoyle King and five miniature gargoyles. New Rogue focused his powers entirely on keeping his goat safe, Shadow Nemesis tried to strike at the king, but hit Del instead, Tyler effectively conjured illusory clones of himself to draw the attention of the gargoyles, and Del psychically attacked with a Cronenberg-like jamboree band. The Doctor Deputy discovered that he couldn’t attack the gargoyle king unless it first attacked every member of the troupe, and with the stone giant swiftly smashing through Tyler’s illusions, will the troupe survive another blow?

Fe...


Wrong Holiday Episode! Jesters of Ravenloft - 2.21 - The Gargoyle King
12/26/2025

Wet Change entered the church in the Nameless Graveyard and, when Del realized it was Thanksgiving, they decided to celebrate and found some food and drinks. Rumpleforeskin made a berry jelly and baked a calzone inside themself, they all played cards, and the Doctor Deputy put on such an incredible show with the Tech Deck that Tyler gave it to him permanently. They all said what they were thankful for, received gifts from the Watchers, including a goat for New Rogue that he can pet without harming, and discovered that Shadow Nemesis had slept with a Sanguine. Now can...


Wrong Holiday Episode! Jesters of Ravenloft - 2.20 - Thanksgiving in Ravenloft
12/26/2025

We've taken the week off so our team can have a holiday before returning with fresh episodes! In the meantime, please enjoy a couple of episodes of Jesters of Ravenloft celebrating a completely different holiday!


In the previous episode...

The troupe left Protection Town and set off toward the Barren Hills. Del got her phone out and shared photos of them all in happier times and New Rogue connected again with Shadow Nemesis by reminiscing about Wet Change’s more bizarre sketches until they arrived at the Nameless Graveyard. Coming upon a ch...


Jesters of Middle-earth - Episode 37 - The King of Moria
12/20/2025

The Fellowgroup fought for their lives as the Watcher in the Water attacked them just outside the door into Moria. Del struggled to escape its grasp, but Guy slashed his way towards her, and Yolo and Denethea pulled them free. A gaunt creature claiming to be Frodo appeared and told Tyler the answer to the door’s riddle, and as the door opened, armoured dwarves hurled axes at the Watcher to cover their escape. Del was suspicious of the dwarves, but after Adam assured her that everything was fine, they let themselves be led inside to see the King of...


Jesters of Middle-earth - Episode 36 - Speak Friend, Idiot!
12/19/2025

The Fellowgroup negotiated with the elves and rangers and agreed that one of each could accompany them to the supposed party taking place in Moria. The troupe became annoyed with Yolo when he revealed his presence to their new travel companions, Guy spoke with Denethea, who mused allowed whether it might be nicer if someone more strong-willed could bear the Ring, and Del guided them all to a rock wall with a strange door next to a smooth lake. As they examined the door, they heard a cry. The ranger was gone and tentacles sprung from the water. Can...


Jesters of Middle-earth - Episode 35 - Horbit Melf Dwork
12/13/2025

The troupe broke camp, Del drank what was left of the navigation whiskey, and the Fellowgroup set off once more. They soon came across several rangers and elves having an argument over jurisdiction in the surrounding area, so Tyler and Del caught up and exchanged their thoughts about Denethea while Adam and Guy left to investigate. The rangers revealed they were also on the lookout for a hobbit carrying illicit jewellery and demanded to speak with the ranger in their Fellowgroup. The troupe regrouped and strategized their approach, but can they talk their way past these aggressive rangers and...


Jesters of Middle-earth - Episode 34 - A Dwarf and an Elf Walk into an Argument
12/12/2025

After a quick flashback to Frodo murdering Grungus Took, the Fellowgroup settled into their camp on the road the Moria. Del slept off her navigation whiskey, Denethea expressed a romantic interest in Del, and Tyler confronted Denethea. The Gondorian confessed she was frustrated that she’d be good ruler if not for her illegitimate birth, so Tyler made a deal that if she helped the Fellowgroup and proved to be a good person, he’d marry her and let her rule. Furthermore, Guy reported that she hadn’t done anything suspicious during her watch. Will the Fellowgroup’s burgeoning sense of...


Jesters of Middle-earth - Episode 33 - The Fellowgroup Goes South
12/06/2025

The Fellowgroup of the Ring left Rivendell and set off towards the Mines of Moria. They took stock of their burgeoning abilities and new weapons: Tyler’s ranger skills and reforged sword; Guy’s keen elf eyes and shiny mithril vest; Adam’s Wario-style everything; and Del’s uncanny ability to navigate while drunk. On the way, Tyler noticed Denethea staying uncomfortably close to him, so Del pretended to need the help of a strong woman and pulled the Gondorian’s focus, and Adam tried to hunt, but the thought of it brought back memories of how Tony Dumdum died. Is a...


Jesters of Middle-earth - Episode 32 - Yeet the Hobbit
12/05/2025

The Fellowgroup met to discuss their upcoming journey to Mordor. Gandalf brought out The Fellowship of the Ring on DVD, complete with a hand-written note from Peter Jackson to one of the film’s actors, and the troupe decided to explain away the synopsis as an alternate path that their journey could take. As they made their final preparations, Adam made an enemy of Glorfindel, Guy was disappointed to find Arwen only to learn she was looking for Tyler, and Arwen gave Tyler his sword, reforged, as a parting gift. They finally departed from Rivendell, but will everyone in th...


One Shots: Avernus - Episode 2
11/28/2025

We're unexpectedly off this week! In the meantime, we hope you enjoy another journey into hell in one of our One Shots: Avernus.


This arc features our awesome DM Tom McGee, Ryan LaPlante as Werner Ragnarok, Tyler Hewitt as Hambone, and Laura Hamstra as the elderly murder machine Maude Buggins! An entire city has disappeared and the members of The Stain were determined to avenge it! Our heroes were chasing down Thavius Kreeg and were forced to fight 3 death cultists. Hambone almost died and a winged demon told him he’d be in hell so...


Introducing... One-Shots: Avernus - Episode 1
11/28/2025

We're unexpectedly off this week! In the meantime, we hope you enjoy another journey into hell in one of our One Shots: Avernus. This 20-episode adventure features players Ryan LaPlante, Tyler Hewitt, and Laura Hamstra, alongside Dungeon Master Tom McGee. If you like these first 2 episodes, you can find the other 18 over at our One Shots podcast!


Enjoying One Shots?

- Consider supporting the show for as little as $1 a month to get BTS fun, an ad-free feed, and even add your own character to the podcast! (https://dumbdumbdice.com/join)

<...


Jesters of Middle-earth - Episode 31 - The DVD of Orthanc
11/22/2025

After an intensive day of councils, death, and crime scene investigation, the troupe settled down for the night. Adam inspected his new armour and was thrilled about its Wario-ness. Tyler was approached by Arwen, who told him they should not be held to a promise made when they were younger. They agreed to reevaluate their relationship after the business with the One Ring was concluded, and Arwen asked after Guy. Guy, meanwhile, fell asleep only to dream of dying at the hands of brutal orcs. Feeling unsettled, he went searching for food, and found Arwen in the kitchens. Could...


Jesters of Middle-earth - Episode 30 - The Complete Uninhibited Guy Experience
11/21/2025

The troupe gathered more evidence at the scene of the crime. Del deduced that the suspect must be short, Tyler noticed that Yolo’s feet were not in fact muddy, and Guy failed to stop Elrond from entering the brothel room. So, back in the privacy of their rooms, they shared their theories. Tyler told them that Grungus had split up Frodo and his boyfriend, Sam, so Grungus clearly had no shortage of enemies with grudges. Plus, they worried about Yolo’s fate if they were wrong, and were aware that he was needed as the ring-bearer, so they deci...


Jesters of Middle-earth - Episode 29 - CSI: Middle-earth
11/15/2025

Grungus Took’s death took the troupe by surprise. Guy and Del investigated the scene of the crime and hoped the trail of muddy footprints would lead them to a suspect. Adam went to report the news to the dwarves, but they wouldn’t let him in to see his father. Even worse, the one dwarf that Adam had actually connected with died suddenly in a freak accident. Tyler was left to console Yolo and talk him through his conflicting feelings, but when he brought Yolo in to see the body, Guy and his keen elven eyes noticed that Yolo...


Jesters of Middle-earth - Episode 28 - A Chorus of ‘WAAAAAH’s
11/14/2025

After Gandalf retold the tale of his imprisonment by Saruman, he told Del that the dwarves suspected that Grungus had sold them out and used the ring to get the dragon’s treasures for himself, so they headed to the brothel to question Grungus directly. Adam and Guy also went there looking for Grungus, but arrived shortly after the others to find the hobbit had been stabbed to death. Meanwhile, Tyler convinced Yolo to trust him, and Yolo revealed that Grungus had stabbed a small riddle-obsessed creature in cold blood to steal the ring. Is there any hope of de...


Jesters of Middle-earth - Episode 27 - The Last Horny House
11/08/2025

With the Fellowgroup’s mission decided, the troupe tied up loose ends in Rivendell. Tyler cleared the air with Denethea and was having a pleasant moment with Arwen when Guy burst in, smitten with the Liv Tyler lookalike. The boys wondered if Arwen was meant to end up with Guy instead. Meanwhile, Adam recalled his character dying in a dragon’s fiery breath and regained his father’s approval, so Gloin asked Adam to check in on their kin at the Mines of Moria, but first they would interrogate Grungus to find out what really happened at the Lonely Mounta...


Jesters of Middle-earth - Episode 26 - Am I a Ghost, Daddy?
11/07/2025

After a surprise meeting with Werner Herzog, the Fellowgroup attended the Council of Elrond, where they learned the history of the Rings of Power and debated what to do with the One Ring. Guy and Tyler both immediately put forth that it should be destroyed, and after some debate, Tyler pointed to Grungus Took as proof that the ring only corrupted people and made them horrible. Gloin then volunteered Adam to help destroy the ring, and Guy, Tyler, and Del all agreed to go on the quest too. The Fellowgroup then began to get healed, armed, and armoured, and...


Jesters of Middle-earth - Episode 25 - The Worst Halfling You’ve Ever Seen
11/01/2025

The Fellowgroup haven’t made any friends in Rivendell. Adam’s kin saw through his lies and beat him up until someone brought news that Grungus Took was nearby, Guy discovered that saying the name J.R.R. Tolkien injured his fellow elves, and at the Gondor camp, Denethea declared she wanted the ring for herself, then stabbed Del when Tyler said it wasn’t theirs to give to her. Del and Tyler were saved by the arrival of Gandalf, and once the wizard got the troupe alone, he revealed that he knew they didn’t belong in Middle-earth and prod...


Jesters of Middle-earth - Episode 24 - Violence at the Last Homely House
10/31/2025

The Fellowgroup arrived in Rivendell and met people who seemed to know them! Guy learned that he’s immortal, his father is the king of Mirkwood, and the other elves want Yolo’s ring for themselves. Del gave Tyler relationship advice about the Arwen situation before they met Denethea, daughter of the Steward of Gondor. Once Tyler assured her that he didn’t want to claim any throne, Denethea spoke about her brothers, Faramir and Boromir, and their fixation on the ring. Adam, meanwhile, cornered himself into improvising the tale of his supposed escape from the Lonely Mountain, but is he c...


Hack N Slash - Episode 4
10/25/2025

During our week off, please enjoy the continuation of our "Monster of the Week" miniseries: HACK N SLASH!


HACK N SLASH is a four-part improvised comedic mini-series featuring Ryan LaPlante as the Keeper, Del Borovic as Shadow Lady, and three new voices: Josh Halbot as Bloody Mark, Kevin Hanna as Tailspin, and Pam Sparrow as Dr. Belladonna. This “Monster of the Week” adventure features four monsters who find out they’re being replaced by upgraded versions of themselves and must fight to stay alive.​


Find more episodes on Spotify (https://o...


Hack N Slash - Episode 3
10/25/2025

During our week off, please enjoy the continuation of our "Monster of the Week" miniseries: HACK N SLASH!


HACK N SLASH is a four-part improvised comedic mini-series featuring Ryan LaPlante as the Keeper, Del Borovic as Shadow Lady, and three new voices: Josh Halbot as Bloody Mark, Kevin Hanna as Tailspin, and Pam Sparrow as Dr. Belladonna. This “Monster of the Week” adventure features four monsters who find out they’re being replaced by upgraded versions of themselves and must fight to stay alive.​


Find more episodes on Spotify (https://o...


Hack N Slash - Episode 2
10/24/2025

During our week off, please enjoy the continuation of our "Monster of the Week" miniseries: HACK N SLASH!


HACK N SLASH is a four-part improvised comedic mini-series featuring Ryan LaPlante as the Keeper, Del Borovic as Shadow Lady, and three new voices: Josh Halbot as Bloody Mark, Kevin Hanna as Tailspin, and Pam Sparrow as Dr. Belladonna. This “Monster of the Week” adventure features four monsters who find out they’re being replaced by upgraded versions of themselves and must fight to stay alive.​


Find more episodes on Spotify (https://o...


Introducing... Hack N Slash - Episode 1
10/24/2025

Due to some unforeseen circumstances, we'll be taking this week off. We'll be back next week, but in the meantime, please enjoy our "Monster of the Week" miniseries: HACK N SLASH!


HACK N SLASH is a four-part improvised comedic mini-series featuring Ryan LaPlante as the Keeper, Del Borovic as Shadow Lady, and three new voices: Josh Halbot as Bloody Mark, Kevin Hanna as Tailspin, and Pam Sparrow as Dr. Belladonna. This “Monster of the Week” adventure features four monsters who find out they’re being replaced by upgraded versions of themselves and must fight to sta...


Jesters of Middle-earth - Episode 23 - A Regular Grungus Took
10/18/2025

With Frodo lost to the flood, the remainder of the Fellowgroup headed to Rivendell, following Arwen, who had stormed off after Tyler couldn’t recall her name. When they arrived at the Elvish sanctuary, Arwen informed them that there would soon be a meeting to discuss the ring. But in the meantime, Adam and Guy’s respective kin were waiting for them, a delegation from Gondor would be eager to learn that Tyler was alive, Yolo’s father was drunk and making a scene, and no one seemed to recognize Del. Can Wet Change convincingly improvise their way through reunio...


Jesters of Middle-earth - Episode 22 - Zip Zap Zop
10/17/2025

The Fellowgroup made a desperate final push across the ford. Guy and the mysterious elf shot arrows at the Ringwraiths while Adam dove underwater and stabbed at the horses from below before making it to shore. At the bank, Tyler reached for Guy and Frodo, but at the last moment, he lost his balance. He managed to grab hold of Guy, but Frodo couldn’t reach and was swept downstream. With Ringwraiths at their heels, the elf confirmed that Yolo had the ring, then triggered an enchantment, causing the waters to rush up and carry the Ringwraiths—and Frodo—away...


Jesters of Middle-earth - Episode 21 - Are You Related to Aerosmith?
10/11/2025

The Fellowgroup faced the Ford of Bruinen, the final obstacle between them and the safety of Rivendell. Guy threw off a few of the pursuing Ringwraiths by shooting Yolo’s bell into the trees, while Yolo encountered a terrifying vision of a great eye. Meanwhile, Adam secured the chain crossing the river, Tyler waded in but became blinded and deafened by the rushing water, and Del tried to get to Tyler but slipped. Guy then attempted to carry the two hobbits plus Del to the opposite bank when an elf appeared, who loosed flaming arrows at the Riders and bi...


Jesters of Middle-earth - Episode 20 - Do You Want Uppies?
10/10/2025

The troupe faced off against the terrifying Ringwraiths! After Guy’s arrow missed its target, he took off with the hobbits to get them out of harm’s way. Del tried to distract the wraiths with a camera flash but got impaled by a sword and Adam threw a barrel at them, but it was Tyler throwing a torch at the wraiths that finally did the trick. They picked up an unconscious Del and escaped to meet Guy and the hobbits at the East Gate. They made for Rivendell, but as they came upon a rushing river in their way...


Jesters of Middle-earth - Episode 19 - The Cloaked Rascals
10/04/2025

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 to the east gate across the rooftops. But even as they ran, terrifying faceless figures in dark cloaks...


Jesters of Middle-earth - Episode 18 - Jimbo Bread
10/03/2025

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 Tyler went to investigate, he was stabbed by a mysterious figure. Back at the Jimothy’s, Guy was then approached by a moth asking about hobbits. Is there...


Canada By Night - 1.02 - The Situation
09/26/2025

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 sheriff’s tastes? Find out now, as we return to the World of Darkness.


Introducing... Canada By Night - 1.01 - Welcome to New Haven
09/26/2025

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 brother in Darkness... but he has no idea what is in s...


Jesters of Middle-earth - Episode 17 - Have You Seen Dumpster Hobbits?
09/20/2025

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 herself. At the Inn, Aaron Fudge was strangely...


Jesters of Middle-earth - Episode 16 - An Elf, a Dwarf, a Ranger, and a Del
09/20/2025

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 longer, Tyler was beefier and brandishing a broken swo...