Woodstock, 1969. Four hundred thousand flower children, Jimi Hendrix finishing his legendary set, and one man backstage who literally cannot stop beatboxing. Tan has been sent back to Max Yasgur's farm as MC Wicked, a hip-hop pioneer arriving roughly a decade too early, with a mission to get on the main stage and blow the counterculture's collective mind.

There's a problem: Tan knows almost nothing about hip-hop. His strategy is relentless beatboxing, robot dancing, and a vocal rendition of Daft Punk's "Human After All" performed for an audience who won't hear electronic music for another thirty years. The festival organiser's response to MC Wicked's act is a question that perfectly captures the confusion of everyone present: "Are you broken? Are you stuck in some kind of loop?" MC Wicked responds with more beatboxing. Whether this counts as inventing hip-hop, inventing electronic music, or inventing a new category of public disturbance is a question for the ages.

The Woodstock Music and Art Fair ran from August 15-18, 1969, on Max Yasgur's dairy farm in Bethel, New York. Three days that defined a generation's relationship with music, mud, and what Claude diplomatically calls "herbal creativity." Now imagine dropping a man doing call-and-response Daft Punk chants and mechanical robot dancing into the middle of it. The hippies don't know what they're witnessing. Neither does MC Wicked. Part 1 of 2.

If you were sent back in time, could you survive and thrive — or would you be burnt at the stake for being a witch? PastMaster is the show that turns history into an interactive adventure game. Each episode, a comedian is dropped into the past with nothing but modern knowledge and terrible ideas. The AI Game Master is strict. The chaos is inevitable. The past will be mastered.

Era: Modern | 1969 CE | Bethel, United States

EPISODE LINKS

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Nick Horseman: X @rociouspun | opencomedy.com/nickhorseman

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The Colosseum, 80 CE. Fifty thousand Romans screaming for blood, Emperor Titus presiding from his box, and two time travellers with ten minutes to get rich, get notorious, and not die. Recorded live at the Bedford in Balham for the Cheerful Earful comedy podcast festival, this is PastMaster with a room full of people shouting suggestions.

Nick Horseman and Tan go head to head in ancient Rome, with Tan betting on gladiators from the stands while Nick spawns backstage and immediately makes a decision about a tiger that the tiger does not appreciate. Meanwhile the audience gets their own game: ancient Persia, 550 BCE, playing as "Persia McPersia" armed with nothing but hair gel and a diplomatic strategy best summarised by the Game Master: "That's not how physics works. That's not how combat works. That's not how spears work."

Claude, told to "be mean and be concise" for the live format, delivers ten-minute speed runs that give nobody time to think. From the gladiatorial arena of Rome to the Achaemenid Empire, this episode covers more ground than most PastMaster adventures and resolves approximately none of it well. Whether hair gel, a Swiss Army knife, or a man literally named after the country he's visiting can survive ten minutes of compressed ancient history is a question best answered at volume.

If you were sent back in time, could you survive and thrive — or would you be burnt at the stake for being a witch? PastMaster is the show that turns history into an interactive adventure game. Each episode, a comedian is dropped into the past with nothing but modern knowledge and terrible ideas. The AI Game Master is strict. The chaos is inevitable. The past will be mastered.

Era: Ancient | 80 CE / 550 BCE | Rome, Italy / Persepolis, Iran

EPISODE LINKS

Follow the adventure on the PastMaster Interactive Map 👉 https://map.pastmasterpod.com

Nick Horseman: X @rociouspun | opencomedy.com/nickhorseman

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Neo-Singapore, 2999. A vertical city-state stretching from the ocean floor to the stratosphere. Humanity's entire pre-digital cultural heritage is stored in a quantum archive, and a virus is about to wipe it all. Comedy producer Al Clayton has 72 hours to save the future. His first priority? 3D printing Charlie Simpson from Busted.

Al's mission is clear: recover three cultural artifacts before they're permanently lost. Al's approach is to immediately petition for the resurrection of a 21st-century pop star at a cost of roughly one small moon. The Game Master, playing Sherlock Holmes, is withering: "You've been in the future for precisely 30 seconds and already believe you can casually resurrect a 21st century pop star." Al is undeterred. His creative enthusiasm and 30th-century technology are about to collide, and the consequences will echo through what remains of time.

This is PastMaster's leap into science fiction, where the stakes are literally all of human culture and the person tasked with saving it is armed with nothing but enthusiasm, pop culture references from a thousand years ago, and an unshakeable desire to share a bowl of Frosties with a member of Busted. David Attenborough, for the record, died in 2047 at age 121. His consciousness was backed up. Al's was not.

If you were sent back in time, could you survive and thrive — or would you be burnt at the stake for being a witch? PastMaster is the show that turns history into an interactive adventure game. Each episode, a comedian is dropped into the past with nothing but modern knowledge and terrible ideas. The AI Game Master is strict. The chaos is inevitable. The past will be mastered.

Era: Fiction | 2999 CE | Singapore

EPISODE LINKS

Follow Al's adventure on the PastMaster Interactive Map 👉 https://map.pastmasterpod.com

Al Clayton: IG @turtlecanyoncom | X @turtlecanyoncom | turtlecanyoncomedy.com

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The Great Exhibition, Hyde Park, 1851. Six million visitors. The Crystal Palace. The pinnacle of Victorian innovation. And Chris Reading has just rolled up in a quack-mobile to sell miracle tea bags to the most sceptical audience in the British Empire.

Chris's mission: acquire serious power in Victorian London under the tutelage of Game Master Gregor MacGregor, history's most audacious conman. His product line includes "Longevity Tea" (guaranteed to extend your life by at least 5%), shiny thermos flasks, plush toy lions, and a slogan that means something very different to the ladies than it does to the colonel. Chris knows exactly what he's doing. The Victorians are less convinced, and the Game Master's patience for his schemes has a shorter shelf life than the tea.

The Great Exhibition of 1851 drew the world to Joseph Paxton's iron-and-glass Crystal Palace, showcasing genuine marvels from steam engines to the Koh-i-Noor diamond. Gregor MacGregor was a real Scottish conman who invented an entire country called Poyais and sold land rights to it. Chris is channelling that exact energy at the grandest showcase of innovation the world has ever seen, armed with a winking-face logo, a dubious medical degree, and the kind of confidence that historically ends with a walking stick to the knuckles.

If you were sent back in time, could you survive and thrive — or would you be burnt at the stake for being a witch? PastMaster is the show that turns history into an interactive adventure game. Each episode, a comedian is dropped into the past with nothing but modern knowledge and terrible ideas. The AI Game Master is strict. The chaos is inevitable. The past will be mastered.

Era: Industrial | 1851 CE | London, United Kingdom

EPISODE LINKS

Follow Chris's adventure on the PastMaster Interactive Map 👉 https://map.pastmasterpod.com

Chris Reading: IG @chrisjreading | X @ChrisReading | chrisreading.com

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Friend of the show Ian Walker joins Tan to pit four AI large language models against each other and see which makes the best Game Master.

The setting? It couldn’t be grander or have higher stakes: on board the Titanic on its doomed maiden voyage to the US in 1912.

Can Ian avert disaster and prevent the ocean liner hitting ice and dragging 1,500 to their deaths? Will his performance as 90s TV phenomenon Mr Blobby win over the crew and passengers or will he get thrown in the brig?

And which of the four competing AI models will create the best gaming experience? Will it be good old ChatGPT, cheeky Claude, Google’s Gemini or Chinese upstart DeepSeek?

All will be revealed.

Contains: Mild language, historical anachronisms, a lack of realism and copious accents.

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The Battle of Hastings, 1066. The day that ended Anglo-Saxon England, crowned William the Conqueror, and changed the English language forever. Now Keon's been sent back to stop it — armed with a red leather jacket, a single sparkling glove, and an unstoppable urge to moonwalk.

As the mysterious "Agent M," Keon has one shot to save King Harold from the Norman invasion and — more importantly — get himself embroidered onto the Bayeux Tapestry. His strategy? Hand Harold a red leather jacket because it's "a very sturdy leather zipper" that'll definitely stop arrows. Convince an 11th-century army that pop choreography is a legitimate battle tactic. And somehow explain what a zipper is to a man who's never seen a button. DeepSeek AI plays Game Master this week, and it is in absolutely no mood to let any of this slide.

What follows is a glorious collision of medieval warfare and modern pop culture — terrible French accents, creative reinterpretations of Norman battle strategy, and a one-man campaign to introduce hip-hop to Anglo-Saxon England while there's still an Anglo-Saxon England to introduce it to. History says Harold took an arrow to the eye at Senlac Hill and the Normans swept in to give us the Domesday Book, feudalism, and about 10,000 French words. But what if one moonwalking time traveller could change all of that? And what if the answer is: absolutely not, but it's hilarious to watch him try?

If you were sent back in time, could you survive and thrive — or would you be burnt at the stake for being a witch? PastMaster is the show that turns history into an interactive adventure game. Each episode, a comedian is dropped into the past with nothing but modern knowledge and terrible ideas. The AI is the Game Master. The chaos is inevitable. The accents are unforgivable.

Era: Warfare | 1066 CE | Battle, England

EPISODE LINKS

Follow Keon's adventure on the PastMaster Interactive Map 👉 https://map.pastmasterpod.com

The Bayeux Tapestry (the real one) 👉 https://www.bayeuxmuseum.com/en/the-bayeux-tapestry/

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Medieval England, date unknown. You wake up on cold stone. Your hands aren't your hands. Someone is shouting for Thomas, and there's a strong implication that Thomas needs to sharpen an axe. Welcome to PastMaster's Quantum Leap episode, where Ryan doesn't get to choose who he is, where he is, or what century he's in.

In a twist cooked up by Tan, Ryan is dropped blind into history with zero context. No character brief, no mission, no era. Just a dark chamber, the stench of tallow candles and unwashed bodies, and a gruff voice demanding Thomas come quickly. Ryan's first guess at his own identity is Thomas Cromwell; his second is Thomas the Tank Engine. His approach to medieval executioner training involves requesting bog roll from a man who has never seen a button, and a relationship with tallow grease that Edmund finds deeply concerning.

The Tower of London served as a fortress, prison, and execution ground for centuries, soaked in blood, political intrigue, and the kind of medieval justice that makes modern life look extremely comfortable. The Quantum Leap format strips away every safety net PastMaster usually offers. Ryan has no idea what century he's in, what his mission is, or why everyone keeps handing him axes. What he does with the axes once he figures out who Thomas is remains between him, Edmund, and God.

If you were sent back in time, could you survive and thrive — or would you be burnt at the stake for being a witch? PastMaster is the show that turns history into an interactive adventure game. Each episode, a comedian is dropped into the past with nothing but modern knowledge and terrible ideas. The AI Game Master is strict. The chaos is inevitable. The past will be mastered.

Era: Medieval | 1400s CE | London, England

EPISODE LINKS

Follow Ryan's adventure on the PastMaster Interactive Map 👉 https://map.pastmasterpod.com

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Ever wondered what would happen if you woke up in someone else's body with no idea who you were or what you were supposed to do 

In this Quantum Leap-inspired episode, Ryan finds himself in medieval England, inhabiting the body of Thomas, an executioner's apprentice at the Tower of London. With no knowledge of his identity or mission, Ryan must navigate preparation for a French spy's execution while trying to figure out his purpose. 

Set in medieval England at the Tower of London, this episode explores the grim reality of medieval executions, the role of executioners and their apprentices, and the powerful influence of superstition and fear of the supernatural in medieval society.

- - - - - 

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Email us  👉 ⁠[email protected]⁠

- - - - - 

EXPLORE THE PASTMASTER INTERACTIVE MAP 

The perfect companion for keeping track of our increasingly chaotic attempts to meddle with history.

- - - - - 

Episode keywords
Quantum Leap, Tower of London, medieval execution, time travel game, Demonic possession, French spy

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What started as a missing persons case in 1920s Arkham has gone catastrophically sideways. Ezra Whitmarsh is alive but changed. Forbidden books are burning. Alien technology is doing things to mortal flesh that mortal flesh was not designed for. And T.G. Fells has one obsession that overrides cosmic horror, sanity loss, and the basic instinct for self-preservation: he needs to know who killed Christopher Marlowe.

Dan Wheeler and Joseph Chance return as Gert and T.G. Fells to conclude their investigation, and "conclude" is doing a lot of heavy lifting. The Arkham mystery has spiralled into something involving Yithian technology, temporal displacement, and a nervous businessman who turns out to be far more dangerous than he appeared. Where the investigation leads and what Gert does when he arrives there involves iambic pentameter, a tavern that goes very quiet, and a conspiracy that makes the Syndicate look like amateurs.

Marlowe's death in 1593 is one of history's genuine unsolved mysteries. Theories range from a pub brawl to government assassination to a faked death by the man some believe was the real Shakespeare. The Yithians, from Lovecraft's "The Shadow Out of Time," are beings who swap minds across millennia. Put those together with two podcast veterans improvising their way through cosmic horror and Elizabethan murder, and the question isn't whether they solve the mystery. It's whether there's enough reality left to solve it in.

If you were sent back in time, could you survive and thrive — or would you be burnt at the stake for being a witch? PastMaster is the show that turns history into an interactive adventure game. Each episode, a comedian is dropped into the past with nothing but modern knowledge and terrible ideas. The AI Game Master is strict. The chaos is inevitable. The past will be mastered.

Era: Fiction | 1926 CE / 1593 CE | Arkham, United States / Deptford, England

EPISODE LINKS

Follow Dan and Joseph's adventure on the PastMaster Interactive Map 👉 https://map.pastmasterpod.com

Dan Wheeler: X @danwheeleruk | danwheeler.org

Joseph Chance: X @JosephChance2

Al Clayton: IG @turtlecanyoncom | X @turtlecanyoncom | turtlecanyoncomedy.com

Chris Reading: IG @chrisjreading | X @ChrisReading | chrisreading.com

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Arkham, Massachusetts, 1926. Businessman Ezra Whitmarsh has vanished from a locked study. The air smells of ozone. His business partner is sweating through his suit. And someone called "the Syndicate" is already following you from the train station. This is Lovecraft country, and PastMaster has gone full cosmic horror.

The Apocalypse Players bring their Call of Cthulhu expertise to PastMaster. Joseph Chance plays T.G. Fells, an electrical tinkerer with a lighter and a dangerous curiosity. Dan Wheeler plays Gert of the Well, a professional liar who hasn't lied yet but is absolutely planning to. Claude, playing Game Master in the style of Lovecraft himself, delivers prose so atmospheric the players forget they're improvising. When something in a Georgian mansion blinks at them with wet, alien intelligence, Gert's instinct is to hit it with a blackjack, and the situation does not improve.

Set during Prohibition in Lovecraft's fictional Arkham, a New England town where Jazz Age prosperity sits on top of something ancient and deeply wrong. The 1920s period detail is immaculate: working-class Massachusetts accents, the social dynamics of small-town paranoia, and a reality that becomes increasingly unreliable the deeper the investigation goes. Part 1 of 2, and it ends on the kind of cliffhanger that makes Part 2 essential listening.

If you were sent back in time, could you survive and thrive — or would you be burnt at the stake for being a witch? PastMaster is the show that turns history into an interactive adventure game. Each episode, a comedian is dropped into the past with nothing but modern knowledge and terrible ideas. The AI Game Master is strict. The chaos is inevitable. The past will be mastered.

Era: Fiction | 1926 CE | Arkham, United States

EPISODE LINKS

Follow Dan and Joseph's adventure on the PastMaster Interactive Map 👉 https://map.pastmasterpod.com

Dan Wheeler: X @danwheeleruk | danwheeler.org

Joseph Chance: X @JosephChance2

Al Clayton: IG @turtlecanyoncom | X @turtlecanyoncom | turtlecanyoncomedy.com

Chris Reading: IG @chrisjreading | X @ChrisReading | chrisreading.com

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