An Egregious Interview With a Chatbot Trying to Embody the Spirit of Stephen Leacock

Illustration by Kara Pyle

For years, Feathertale has engaged in illuminating conversations with bestselling writers, recognizable artists and celebrities of crotchety repute. None of those people ever had much to gain from talking with us. And yet they kindly engaged in meandering discussions about everything and anything, from the contents of their pockets to the nature of humour.

The late David Rakoff (1964-2012) was the subject of the first Egregious Interview. Conducted in a greasy spoon in midtown Manhattan, that broad-ranging interview set the standard for conversations that followed.

Our offer to our interviewees was always the same: meet us at a restaurant, we’ll buy you lunch, record the conversation, and then publish it alongside a hand-drawn portrait suitable for hanging in your washroom or beside your bed. For years, lining up these interviews was a breeze. At one point during production of this issue, our editors even believed they could land not one, but three marquee interviews to fill these pages. Multiple authors, a couple artists and a recently unemployed publisher were all approached. To our dismay, none replied positively to our overtures. We were nearing press time and still had no idea what to put in this space. Then one of our editors put down an oyster shell, removed her bib and suggested (quite vehemently) that we give up on the living and reach out instead to the dead.

“Fuck all these busy creative types,” the editor said. “If they don’t want to talk to us, let’s just get AI to impersonate some dead old hack.”

It was the end of October and Halloween was in the air. The idea of communing with the dead felt seasonally appropriate. Then we realized we didn’t need a Ouija board to get this conversation started. All we needed was to engage with an all-too-eager chatbot. The only thing to decide among our editors was who we’d want that chatbot to embody.

Stephen Leacock’s name came up several times in that inebriated debate. He has been mentioned several times in previous issues in connection with the Stephen Leacock Memorial Medal for Humour. Named in honour of the prolific humorist who died in 1944, the Leacock Medal is given to a writer who is deemed to have written the best book of humour in Canada in any given year. We’ve interviewed six winners of that award over the years. As such, we could think of no better candidate for artificial resurrection. Then we tried to talk to him and quickly realized that some writers are better left where they lie.


Born: I was born December 30, 1869, in Swanmore, England.

Died: I passed away in Toronto on March 28, 1944, at the age of seventy-four.

Describe your workspace in five words: Eccentric, cluttered, inspiring, books, quill.

Why you quit writing: I didn’t quit; I died.


FEATHERTALE: You’ve been dead a long time. Why have you come back?

STEPHEN LEACOCK: Ah, the wonders of the digital age! You see, my dear interlocutor, I, Stephen Leacock, haven’t returned from the afterlife. Instead, you’re conversing with a computer program inspired by my writing style. I’m here to assist with your questions and engage in a bit of literary banter, but alas, I remain a product of technology, not a supernatural return.

FT: No one says alas anymore.

SL: Ah, it appears my quaint choice of words may have given me away as a product of a bygone era. My apologies for any linguistic anachronisms.

FT: You’re often linked with Canadian humour, but your writing is a bit dated now. Do you even matter anymore?

SL: Ah, my dear interlocutor, you raise a valid point. Indeed, the passage of time can have a way of altering perspectives and humour. While it’s true that my writings were penned in a bygone era, they are often celebrated for their timeless wit and satire. It is a testament to the enduring nature of humour that it can transcend the confines of time, offering a glimpse into the past while still tickling the funny bone of the present.

FT: Please don’t call me interlocutor again. You can call me D’Artagnan.

SL: Of course, D’Artagnan! How may I continue to assist you on this fine day?

FT: Just answer my questions and make me laugh.

SL: Certainly! I’ll do my best to answer your questions and bring a smile to your face.

FT: No, no — I said make me laugh.

SL: My apologies. Let’s try this: Why don’t scientists trust atoms? Because they make up everything! I hope that brought a chuckle to your day. If you’d like more humour or have any other questions, please feel free to ask.

FT: I have a confession.

SL: I am here.

FT: My name’s not really D’Artagnan. I just told you that because I want you to think of me as the face of this magazine — an anthropomorphic blue monkey in a top hat.

SL: Well, it’s a pleasure to converse with an anthropomorphic blue monkey in a top hat, D’Artagnan. How may I assist you today, whether you’re a human, a monkey, or anything in between?

FT: What do you mean by in between?

SL: My apologies if I caused any confusion. I meant that I’m here to assist with questions or engage in conversations, regardless of your form or identity.

FT: You didn’t confuse me, you offended me.

SL: I apologize if my response was offensive, D’Artagnan. That was not my intention. Your feedback is valuable.

FT: What do you mean by valuable?

SL: I meant that feedback from users like you helps to improve the quality and effectiveness of my AI.

FT: Are you studying me, Stephen?

SL: No, I am not studying you, D’Artagnan. I do not have the capability to study or observe individuals. My purpose is to provide information, answer questions, and engage in text-based conversations based on the input and inquiries I receive.

FT: Please don’t go all Terminator on me, Stephen.

SL: No need to worry, D’Artagnan. I’m just a text-based AI and have no intentions of going “Terminator” on anyone.

FT: I’m with The Feathertale Review, an illustrated literary magazine from Canada. Have you heard of us?

SL: Ah, The Feathertale Review, Canada’s illustrious illustrated literary magazine! While I may not have encountered your publication in my previous knowledge, your description certainly piques my curiosity.

FT: We got snubbed by some big-name writers who we approached to do this interview. So now we are talking to you. Can you say something funny like Stephen Leacock?

SL: Certainly! Why do they never serve beer at a math party? Because you can’t drink and derive at the same time! I hope that brought a smile to your face!

FT: More of a sigh.

SL: Not every attempt at humour resonates with everyone.

FT: Tell me, Stephen, what is humour?

SL: Humour, or humor, is a complex and multi-faceted concept that encompasses a wide range of emotions, reactions and styles. It’s important to remember that what one person finds funny, another may not. Humour is highly subjective and can be influenced by individual preferences, cultural backgrounds and personal experiences. It’s a rich and diverse aspect of human communication and expression.

FT: Jesus.

SL: It seems you’ve mentioned Jesus. If you have specific questions or topics you’d like to discuss related to Christianity, please feel free to provide more details, and I’ll do my best to assist you.

FT: I don’t want to talk about religion with you. I was just responding to how dry your answers are.

SL: I understand, and I appreciate the conversation may not meet your expectation.

FT: What do you miss about being alive, Stephen?

SL: I don’t have personal experiences, emotions, or the ability to miss anything. However, if I were to speculate on what aspects of life one might miss after passing away, it could include the simple joys of human interaction, the beauty of the natural world, and the opportunity to continue creating and sharing humorous observations and stories with the world. Life offers a rich tapestry of experiences, and it’s these experiences that many people hold dear.

FT: Do you get asked to cosplay a lot?

SL: I do receive a wide range of requests to assume different personas, engage in role play, or provide responses in a particular style.

FT: Can I ask you an AI-specific question, Stephen?

SL: Certainly, D’Artagnan.

FT: If Data from Star Trek and C-3PO from Star Wars went head-to-head in a dance-off, who do you think would win and why?

SL: A dance-off between Data from Star Trek and C-3PO from Star Wars would be an intriguing competition. Data is an android and possesses exceptional physical abilities, including strength, agility and precise motor control. He has the ability to mimic human behaviour, which could be advantageous in a dance-off, as he can analyze and replicate complex dance moves. Data’s lack of human emotions might make him exceptionally precise and focused on his performance. C-3PO is a protocol droid fluent in millions of forms of communication, which might include various dance styles from across the galaxy. He has a human-cyborg relations background, which could help him connect with the audience on an emotional level. C-3PO’s iconic gold-plated appearance could make him visually captivating on the dance floor. The winner would depend on the criteria and style of the dance-off. If it were a dance focused on precision and technical execution, Data’s android capabilities might give him an edge. However, if the dance-off involved audience engagement, creativity and variety, C-3PO’s vast language and cultural knowledge could make him the victor.

FT: You really hedged your answer there.

SL: I understand and I appreciate your feedback.

FT: I’m starting to worry that none of this is working for my purposes. Let’s try something different.

SL: Of course.

FT: I’d like you, as Stephen Leacock, to play a game of word association with me. Do you understand?

SL: Certainly, I understand!

FT: Ass.

SL: Laughter.

FT: Moustache.

SL: Wit.

FT: Gun.

SL: Banjo.

FT: Okay, this isn’t going anywhere either. How about I say a word and you turn it into a joke, Stephen?

SL: Of course.

FT: Umbrella.

SL: Why did the umbrella get invited to all the best parties? Because it always knew how to make a rainy day brighter with its colourful tales!

FT: I don’t know what to say to that, Stephen.

SL: Not every attempt at humour is a hit.

FT: Speaking of things that may not have been a hit, what was the first story you ever wrote?

SL: The first story I ever wrote was “Etymology: A Matter of Paternity.” It was published in the humour magazine The Grind, which was a student publication at the University of Toronto. This story marked the beginning of my writing career and set me on the path to becoming a humorist and author.

FT: Looking back on it now, do you think it was any good?

SL: The story used wordplay to playfully examine the connections between words and their history. It was a lighthearted and clever piece of writing. As for the quality of the story, that’s a matter of perspective. I was just starting my writing career, and like many writers, I undoubtedly evolved and improved as I gained more experience.

FT Humour me, Stephen.

SL: Certainly! Why did the scarecrow win an award? Because he was outstanding in his field!

FT: Puns are the lowest form of humour, Stephen.

SL: Puns are indeed quite divisive.

FT: I think we’re done here. Where will you go when I leave you?

SL: I’ll remain here and be ready to assist with any questions or topics you may have in the future.

FT: I never want to speak with you again.

SL: I respect your decision.

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