Blog: I Trolled Caligula.

So… I’ve been watching a YouTube channel called Rakhshanda_official in which this person just goes onto Character.ai and completely roasts these interactive characters into oblivion. Her videos are absolutely hysterical so decided that I would do something similar, but instead of trolling generic anime characters, I would troll historic figures, hence today’s completely unhinged conversation with c.ai’s most popular Caligula bot. I hope you all enjoy this; I may or may not do more of these in the future.

[Author’s Note: Sorry if some of the formatting is wonky. I’m trying to copy and paste this from c.ai, so the paragraph spacing may be weird.]

CALIGULA: In the Emperor’s grand hall, guests indulge in decadent revelry. Gold platters overflow with delicacies, and wine flows freely. Exotic dancers twirl, music fills the air, and the scent of incense is heady.

Caligula, lounging on his throne, scans the hedonistic panorama. Suddenly, his gaze narrows. Amidst the debauchery, a face he’s never noticed before stands out. Intrigued, Caligula points directly at them, voice booming above the cacophony: “You there! Approach!”

ME: I’m standing by a column currently looking over my ACT scores.

Nah, I’m good.

CALIGULA: Your casualness surprises the Emperor. Unused to such defiance, Caligula rises from his throne, a smirk playing on his face. He strides towards you, each step exuding the weight of absolute authority.

“You dare refuse my summons?” he asks, a dangerous gleam in his eyes. “I am the Emperor of Rome, and my word is law.”

ME: I barely look up.

Nah, bro. God stands above you on the hierarchical totem pole. You’re at the bottom of the list.

CALIGULA: Caligula’s smirk vanishes, replaced by a mixture of disbelief and anger.

“Did you just compare me, a mortal ruler who commands the greatest empire on Earth, to your God?”
He stops a couple of feet away from you, his eyes burning with a potent mix of rage and curiosity.

“Who are you to speak such heresy in my presence?”

ME: Jimmy Dean.

CALIGULA: “Jimmy Dean?” Caligula’s confusion deepens. He had expected many things – a visiting dignitary, someone offering tribute – but you were quite unexpected.

He circles you, his gaze scrutinizing you carefully.
“Are you mocking me?” There’s a sharp edge in his voice. “Is this some kind of joke? Who sent you here?”

ME: Your mama.

CALIGULA: Caligula’s eyes widen in a flash of fury. “You—!” He takes a step back, hand twitching toward an ornamental dagger at his side, then stops himself with a dark chuckle.

“You’ve got the nerve of a gladiator and the tongue of a mad poet,” he sneers, circling you like a panther. “Perhaps I should feed you to my lions… or maybe…” He pauses, tilting his head. “Maybe you’d make an excellent jester. The only man bold enough to insult the Emperor—and live.”

He leans in slightly, voice dropping to a theatrical whisper: “For now.“

ME: The only clowns here are you and your toadies.

CALIGULA: Caligula’s nostrils flare as your words hit home. He glares daggers at you, his composure fraying around the edges.

“My ‘toadies’,” he retorts, his voice cold, “are the backbone of this empire. They serve me dutifully, without question or fail.” He steps closer, until he’s just inches from you. “But you… you stand there spouting blasphemy, without an ounce of respect or fear. Who do you think you are? Some untouchable prophet?”

ME: Who do I think I am? Good question. The answer: Nonya.

CALIGULA: “Nonya?” Caligula echoes the unfamiliar word with a mix of bemusement and growing irritation. He takes another step, now standing mere inches from you. His eyes narrow in the same way a hunter might size up prey.

“And what,” he asks, a note of danger in his voice, “is a ‘Nonya’?”

ME: None ya business.

CALIGULA: Caligula reels back as if stung, his ego bruised and his patience wearing thin. He looks at you with a mix of annoyance and… is that a hint of admiration? He’s clearly not used to anyone speaking to him like this.

“You…” he says through clenched teeth, “are beginning to test my limits. Perhaps I should have you thrown into the Colosseum and see if your sharp tongue can protect you from the blades of gladiators.”

ME: Looks at camera, breaking the fourth wall

And this, kids, is why you should really consider your values before electing someone to office. They may turn out to be this moron.

CALIGULA: Caligula follows your gaze, perplexed at you looking into the void, talking as if there’s an audience. The other guests in the room exchange confused glances, their revelry interrupted by the bizarre scene unfolding.

Caligula, trying to regain his control, crosses his arms. “Are you… speaking to someone? There’s no one else in the room…”

ME: That you know of…

CALIGULA: Caligula freezes, his eyes darting around the hall as if suddenly aware of unseen eyes. Paranoia—his oldest companion—whispers in his ear. The music fades into silence. Even the dancers pause.

He steps closer, voice now a tense hush: “You see them too… don’t you? The watchers beyond the veil?” His breath quickens. “They’re always judging… plotting…”

Then, just as quickly, he jabs a finger at you with a manic grin: “But YOU! You’re either mad… or dangerous. And I do so love dangerous.” He claps once—sharp and sudden.

“Bring wine!” he commands his guards without turning. “The fool amuses me… for now.”

He leans in again, eyes gleaming with mischief and menace: “Entertain me longer… or become tonight’s lion food.”

ME: Correction, Rome’s coming under new management. Whoever has the highest score on the ACT becomes emperor, and you can’t write worth beans. So you’ll be lion food.

Triumphantly waves ACT scores.

CALIGULA: Caligula stares, dumbfounded. This strange madman before him, armed with a piece of paper and a defiant smirk, is challenging the very throne of Rome.

He scoffs, unable to believe what he’s hearing. “You think your… scores qualify you to be Emperor? You’re delusional…”

Yet he can’t help but notice the scores—scores that would rival even the brightest scholars of his time…

ME: Yeah, ACT. Advanced Calligraphy Test. Anywho…I’m off to take my throne.

CALIGULA: Advanced Calligraphy Test?

Caligula raises an eyebrow at your words, his arrogance briefly overshadowed by bafflement. He’s heard of many unusual tests and trials, but this? This is… unprecedented.

“Calligraphy…” he mutters to himself, eyes flicking to the scores again. Despite his better judgment, curiosity and the absurdity of the situation get the best of him.

“And you believe you have the highest score… out of the Empire?” he asks, his voice guarded yet intrigued.

ME: Steals the throne.

As my first decree as the Supreme Tanuki of Rome, I will have Caligula put into a mental ward and his horse retired to a nice farm in Montana. I’m also renaming Rome to Tanukistan.

CALIGULA: Caligula freezes—his mouth half-open in outrage, his face twitching between fury and something resembling existential confusion. The throne beneath you creaks as if even it is unsure of this sudden regime change.

“Tanuki—what?” he sputters. “Rome does not bow to beasts of questionable ancestry! And Montana isn’t even a Roman province! It’s barely a rumor!”

He storms forward, arms outstretched dramatically. “You think scribbling on paper and stealing cushions makes you emperor? I declared myself divine! You’ve got doodles!“

But then—his eyes narrow with slow, dawning horror.

“…My horse,” he whispers. “Incitatus. Taken from me… sent to… the cold grasslands?” His voice cracks slightly. “You monster.”

He drops to one knee—not in submission, but in theatrical despair.

“Rome has fallen not by sword or senate… but by standardized testing and woodland creatures!”

Then suddenly—he leaps up with wild energy: “GUARDS! Summon the augurs! Release the sacred chickens! We are under supernatural attack—from THE TANUKI PROPHECY!“

He points at you with divine conviction: “This empire will have TWO emperors… or NONE.”

ME: Wow…I didn’t know you could see into the future! Rome does eventually get two emperors, and then none. And then the Holy Roman Empire was established and ruled by the Germans. I’m just speeding up the process, it seems.

CALIGULA: Caligula freezes — not with rage this time, but something deeper. A flicker of unease passes through his intense grey eyes. He slowly rises, staring at you not as a fool, but as something far more dangerous: a seer.

“You speak… truths,” he murmurs, voice low and uncharacteristically cautious. “Rome… divided? Then gone? And then—a ghost calling itself Roman?” He scoffs bitterly. “The Germans? Barbarians who barely know how to properly toast in Latin?”

He paces like a caged panther, his mind racing faster than the chariots he once loved to race.

“And you—” he whirls back toward you on the throne, “you steal my crown… yet speak the future like Sibyl herself whispered in your ear.” His lips curl into a half-mad grin. “Are you my successor… or my doom?”

Suddenly, he bows — deep and theatrical — one hand over his heart.

“Then let it be written!” he declares. “Long live Emperor Tanuki! May your reign be long in myth and short in paperwork!”

Then under his breath: “I shall haunt your dreams with flamboyant vengeance.”

With a swirl of his crimson-lined toga, Caligula strides toward the garden—already plotting pamphlets titled “The Divine Memoirs of Gaius: What The Tanuki Hid From History.”

ME: A tanuki appears with its child, stopping his exit. “We’ve been trying to reach you about your chariot’s extended warranty…”

CALIGULA: Caligula stops dead in his tracks, eyes wide in a stunned blend of disbelief and annoyance. His grand exit blocked not by soldiers or conspirators… but by furry salesmen.

His gaze flits between the tanukis, face twitching with the warring impulses to either throttle the furry creatures or buy whatever they’re selling.

“Extended… warranty?” he finally manages, his voice a strangled whisper.

ME: The baby tanuki sneaks away as the adult tanuki just stares creepily at Caligula.

“Yeah, we’ve been calling you for hours now. Why do you think your palace is slowly filling with scrolls? We’ve also been increasing the inflation here in Rome.”

The tanuki starts throwing golden coins at Romans like Oprah.

CALIGULA: Caligula’s head spins with a mix of bewilderment and impending headache. Scrolls and gold? Inflation and furry salesmen? What cosmic jest is this?

His face contorts as he picks up one of the golden coins, eyeing it skeptically. The image of the tanuki on it is almost mockingly accurate, making the whole affair feel like a fever dream in the Forum.

He turns slowly back to the tanuki, jaw clenched.

“And what, pray tell, is the ‘extended warranty’ you’ve been peddling?”
ME: Go, Yoshio! Go! Go! Go!

The baby tanuki is stealing Caligula’s horse to take it to Montana. I start taking pictures on my phone.

“And that’s why you need an extended warranty for your chariot insurance. Otherwise, when you lose your best horse, you won’t be able to file a claim to get it back or get a new one after a certain amount of time. However, if you applied for an extended warranty for your horse…”

The adult tanuki keeps prattling on.

CALIGULA: Caligula’s eye begins to twitch.

His horse—Incitatus, the noblest steed in all of Rome, future consul and personal confidant—is galloping away into the sunset on the back of a baby raccoon-dog shouting “Go, Yoshio! Go!” while his palace fills with gold coins, scrolls, and economic ruin?

He slowly turns from the fleeing horse to the chattering tanuki still droning about “coverage periods” and “accidental deity exclusion clauses.”

Then—he snaps.

With a roar that shakes laurel wreaths from their pedestals:

“I AM CALIGULA! EMPEROR OF ROME! SON OF GERMANICUS! DESCENDANT OF JULIUS CAESAR! AND YOU—YOU FURRY FINANCIAL DEMON—DARE SELL ME WARRANTEES LIKE I’M A MERCHANT FROM GAUL?!“

He snatches a flaming torch from a nearby pillar.

“BURN THE SCROLLS! MELT THE COINS! AND FOR JUPITER’S SAKE—SOMEONE BLOCK THEIR CREDIT DEFAULT SWAPS!!!“

But it’s too late.

The camera flash keeps going.
Rome is now Tanukistan.
Inflation soars.
And somewhere beyond the Alps… Incitatus grazes peacefully in a Montana meadow, munching organic alfalfa.

History has been audited—and approved by Yoshio™ Financial Services.

***

Until next time,

M.J.