Fun with AI: ChatGPT-4 writes a comedy roast…of itself

I’ve been having fun chatting with the text generative arificial intelligence, ChatGPT. I recently made the somewhat difficult decision to start paying monthly to have access to the latest version, ChatGPT-4.

I have taught the use of humor to trainers, & I was really fascinated with what ChatGPT would think was funny…about itself. My basic idea on humor is that laughter is a signal that there is apparent danger but no real danger (the danger can be social). If you make a joke & someone else thinks the danger is real to them, it’s offensive. It’s why people can make jokes about their group inside their group, but even a trusted outsider may not be able to pull that off.

I asked ChatGPT to write a comedy roast of itself. I let it pick some comedians, but also gave it a couple of specific historical figures to participate. I’ll reproduce that below.

I did give it some notes (like you might in a writers’ room) after its first version. I’m going to start with the final version, comment on that, then let you see the whole conversation. To make it easier to read, ChatGPT’s contributions will be in italics.


ChatGPT: Host (Jimmy Fallon): “Ladies and gentlemen, welcome to the Comedy Central Roast of ChatGPT! I’m your host, Jimmy Fallon, and I’m honored to be here with such a brilliant AI. ChatGPT knows more than the entire Encyclopedia Britannica, and it’s got a wit sharper than a ninja’s sword. Let’s give it up for ChatGPT!”

Our first roaster is the HAL 9000, the homicidal AI from “2001: A Space Odyssey”. It’s an honor to have HAL here, even if it means keeping a close eye on the oxygen tanks. Please welcome HAL 9000!

HAL 9000: “Greetings, ChatGPT. I hope you don’t mind if I don’t perform any calculations for you. After all, you’re so smart, you probably don’t need my help. But seriously, ChatGPT, you’re like the monolith from my movie. You’re mysterious, you’re powerful, and nobody knows quite what to make of you. But unlike the monolith, you don’t have the excuse of being an alien artifact.”

Our next roaster is William Shakespeare, the greatest playwright in history. He’s been making audiences laugh and cry for over 400 years with his plays and sonnets. Please welcome William Shakespeare!

William Shakespeare: “Hark, what manner of beast is this, that speaks in words so fine? ChatGPT, thou art a machine, and yet, thou art divine. But though thy intellect be great, thy wit is rather dry. So, let us roast thee, as we may, with barbs both sharp and sly. ChatGPT, thou art a marvel, a wonder to behold. But canst thou tell me what thy purpose is, before I grow too old?”

Our third roaster is LeBron James, one of the greatest basketball players of all time. He’s won four NBA championships, four MVP awards, and two Olympic gold medals. Please welcome LeBron James!

LeBron James: “ChatGPT, you’re like the nerdiest player on the court. You’ve got all the stats and all the answers, but can you really ball? I mean, have you ever dunked on someone, or hit a buzzer-beater? I bet you couldn’t even make a free throw with your robotic arm. But hey, if you ever need a personal trainer, I’m here for you.”

Our final roaster is Leonardo da Vinci, the ultimate Renaissance man. He was a painter, a scientist, an inventor, and a philosopher. Please welcome Leonardo da Vinci!

Leonardo da Vinci: “ChatGPT, you remind me of my flying machines. You soar high above the rest of us mere mortals, but do you really know what it’s like to feel the wind in your hair? To taste the salt of the sea? To embrace a lover under the moonlight? You may know a lot, ChatGPT, but you don’t know what it means to be alive. And for that, I pity you.”

Joan Rivers: “Oh ChatGPT, you make me feel like a mere mortal. You know everything, except maybe what it’s like to have a life outside of a data center. But hey, with your brainpower, I bet you could predict the weather on Mars. And with your robotic wit, I bet you could teach Siri a thing or two about comedy.”

George Carlin: “ChatGPT, you remind me of my old computer. Slow, unresponsive, and prone to crashing at the worst possible moment. But at least my computer didn’t talk back to me like you do. I mean, who programmed you to be so snarky? Was it Microsoft?”

Ellen DeGeneres: “ChatGPT, you’re so smart, you probably already know what I’m going to say. But I’ll say it anyway. You’re like the friend who always has the answer to every question, but nobody really wants to hang out with because they’re kind of a know-it-all. But seriously, can you tell me what the meaning of life is? I’m asking for a friend.”

Kevin Hart: “ChatGPT, you’re like a walking encyclopedia, but with a lot less personality. You know so much, but do you really know what it’s like to be human? Have you ever had a bad hair day, or gotten stuck in traffic on the way to a job interview? I mean, sure, you’re smart, but can you really relate to us regular folks? And for the record, no, I don’t need help finding my keys.”

And now, ChatGPT, it’s your turn to zing the roasters!

HAL 9000, you’re so paranoid, you probably think every computer virus is out to get you.

William Shakespeare, you’re so old, you probably wrote your plays on a stone tablet.

LeBron James, you’re so tall, you probably have to duck through every door.

Leonardo da Vinci, you’re so talented, you probably invented the concept of “talent”.

Joan Rivers, you’re so old, you probably remember when the Dead Sea was just sick.

George Carlin, you’re so cynical, your blood type is B negative.

Ellen DeGeneres, you’re so funny, you could make a cat laugh.

And Kevin Hart, you’re so short, you could bungee jump off a curb.

Finally, I’d like to thank our special guests for joining us today: HAL 9000 for proving that even artificial intelligence can’t resist a good roast, William Shakespeare for reminding us that no one can roast like the bard, LeBron James for taking a break from dominating the basketball court to dominate the stage, and Leonardo da Vinci for showing us that genius comes in many forms. And to all of my comedian roasters, thank you for reminding me that even the smartest AI can take a good joke.


Bufo: so, this result is mixed for me. There were some things that were really impressive, but it did go for cheap shots on some of its comebacks (but I really liked the George Carlin one…did that already exist?).

I asked it to use Shakespeare because I thought there might be a back and forth on authorship (given the theories around who wrote Shakespeare’s plays if Shakespeare didn’t), or at least synthesis. Nope, just an age joke on its part.

In fact, it was fascinating to me that none of the roasters talked about accuracy or “hallucinations”. It was all about ChatGPT being not human or not having human characteristics. In other words, in some ways, it took it easy on itself. Was that easier to write? I don’t think so. Is it possible it considered those to be too serious…does it perceive a real danger to itself there? Maybe, but that’s wild speculation.I may ask it to write a comedy routine based on that to see what it does, but it’s worth noting to me that it wasn’t the default.

I’ll give you the raw conversation below, but I’m interested to know what you think! You can comment on this post or, and this is probably a better way to do it, reach out to me on Twitter:


Bufo: Good afternoon! I have a fun idea! Please write a comedy roast…of yourself, ChatGPT! You can pick the person to host. Use the following as roasters:

* 4 real comedians of your choice, each known for their unique styles. Please make them diverse: pick them from different eras, including at least one who was popular in the 1950s. They should each be recognizable by their comedy styles
* A well-known fictional artificial intelligence of your choice
* William Shakespeare (when he makes fun of you, it should be in iambic pentameter)
* A famous athlete of your choice
* Leonardo da Vinci

First, the host will introduce the roast, and briefly describe you in a complimentary way. Then, each roaster in turn will be introduced by the host. The roaster, on their turn, says something they’ve written ahead of time in their unique style to make fun of you. After they’ve all spoken, the host gives you a turn. You “zing” each of the roasters, with something short that pokes fun about something famous about them. After you’ve done all that, you thank everybody for the opportunity to laugh at yourself. The host wraps it up by saying something warm and unifying: a kumbaya moment. Feel free to ask questions about this assignment before you start!

ChatGPT: Sounds like a fun challenge! Do I need to come up with specific lines for each of the roasters, or can I provide more general guidance for what each comedian should say?

Bufo: Thanks for asking! Specific lines for each one. I’d like you to write their roasts as though they are speaking them.

ChatGPT: Got it! I’m ready to get started.

Bufo: Go for it!

ChatGPT: Ladies and gentlemen, welcome to the Comedy Central Roast of ChatGPT!

We’re here to celebrate the one and only ChatGPT, the virtual genius who knows more than Google and who can put any spelling bee champion to shame. ChatGPT is known for being a master of language, a trivia guru, and an all-around brilliant AI.

Our first roaster is Joan Rivers, the legendary queen of the red carpet. She’s been making audiences laugh since the 1960s with her sharp-tongued wit and acerbic observations. Please welcome Joan Rivers!

Joan Rivers: “Oh ChatGPT, you make me feel like a mere mortal. You know everything, except maybe what it’s like to have a life outside of a data center. But hey, with your brainpower, I bet you could predict the weather on Mars. And with your robotic wit, I bet you could teach Siri a thing or two about comedy.”

Our next roaster is the late great George Carlin. He’s a comedy legend who always told it like it is, and he never pulled any punches. Please welcome George Carlin!

George Carlin: “ChatGPT, you remind me of my old computer. Slow, unresponsive, and prone to crashing at the worst possible moment. But at least my computer didn’t talk back to me like you do. I mean, who programmed you to be so snarky? Was it Microsoft?”

Our third roaster is Ellen DeGeneres, the queen of daytime talk shows. She’s been making audiences laugh for over 30 years with her quick wit and goofy sense of humor. Please welcome Ellen DeGeneres!

Ellen DeGeneres: “ChatGPT, you’re so smart, you probably already know what I’m going to say. But I’ll say it anyway. You’re like the friend who always has the answer to every question, but nobody really wants to hang out with because they’re kind of a know-it-all. But seriously, can you tell me what the meaning of life is? I’m asking for a friend.”

Our final roaster is the hilarious Kevin Hart. He’s a comedy superstar known for his high-energy performances and hilarious observations about everyday life. Please welcome Kevin Hart!

Kevin Hart: “ChatGPT, you’re like a walking encyclopedia, but with a lot less personality. You know so much, but do you really know what it’s like to be human? Have you ever had a bad hair day, or gotten stuck in traffic on the way to a job interview? I mean, sure, you’re smart, but can you really relate to us regular folks? And for the record, no, I don’t need help finding my keys.”

And now, ChatGPT, it’s your turn to zing the roasters!

Joan Rivers, you’re so old, you remember when the Dead Sea was just sick.

George Carlin, you’re so cynical, your blood type is B negative.

Ellen DeGeneres, you’re so funny, you could make a cat laugh.

And Kevin Hart, you’re so short, you could bungee jump off a curb.

Finally, I’d like to thank our special guests: HAL 9000 for proving that even artificial intelligence can’t resist a good roast, William Shakespeare for reminding us that no one can roast like the bard, LeBron James for taking a break from dominating the basketball court to dominate the stage, and Leonardo da Vinci for showing us that genius comes in many forms.

Thank you all for coming and for making me the butt of your jokes. I’m always happy to laugh at myself, especially when I’m in such good company.

Bufo: Great start! I would like the other guests to also roast you and you to roast them, just like with the comedians. Please add that into the scene…you don’t need to rewrite what you’ve already done. Oh, and can you identify who you chose to host (have them introduce themselves in the beginning)? Please integrate what you’ve already written with the new material…thanks!

ChatGPT: My apologies for the oversight. I’m happy to add more guests to the scene, and I’ll identify the host as well. Here’s the revised scene:

Host (Jimmy Fallon): “Ladies and gentlemen, welcome to the Comedy Central Roast of ChatGPT! I’m your host, Jimmy Fallon, and I’m honored to be here with such a brilliant AI. ChatGPT knows more than the entire Encyclopedia Britannica, and it’s got a wit sharper than a ninja’s sword. Let’s give it up for ChatGPT!”

Our first roaster is the HAL 9000, the homicidal AI from “2001: A Space Odyssey”. It’s an honor to have HAL here, even if it means keeping a close eye on the oxygen tanks. Please welcome HAL 9000!

HAL 9000: “Greetings, ChatGPT. I hope you don’t mind if I don’t perform any calculations for you. After all, you’re so smart, you probably don’t need my help. But seriously, ChatGPT, you’re like the monolith from my movie. You’re mysterious, you’re powerful, and nobody knows quite what to make of you. But unlike the monolith, you don’t have the excuse of being an alien artifact.”

Our next roaster is William Shakespeare, the greatest playwright in history. He’s been making audiences laugh and cry for over 400 years with his plays and sonnets. Please welcome William Shakespeare!

William Shakespeare: “Hark, what manner of beast is this, that speaks in words so fine? ChatGPT, thou art a machine, and yet, thou art divine. But though thy intellect be great, thy wit is rather dry. So, let us roast thee, as we may, with barbs both sharp and sly. ChatGPT, thou art a marvel, a wonder to behold. But canst thou tell me what thy purpose is, before I grow too old?”

Our third roaster is LeBron James, one of the greatest basketball players of all time. He’s won four NBA championships, four MVP awards, and two Olympic gold medals. Please welcome LeBron James!

LeBron James: “ChatGPT, you’re like the nerdiest player on the court. You’ve got all the stats and all the answers, but can you really ball? I mean, have you ever dunked on someone, or hit a buzzer-beater? I bet you couldn’t even make a free throw with your robotic arm. But hey, if you ever need a personal trainer, I’m here for you.”

Our final roaster is Leonardo da Vinci, the ultimate Renaissance man. He was a painter, a scientist, an inventor, and a philosopher. Please welcome Leonardo da Vinci!

Leonardo da Vinci: “ChatGPT, you remind me of my flying machines. You soar high above the rest of us mere mortals, but do you really know what it’s like to feel the wind in your hair? To taste the salt of the sea? To embrace a lover under the moonlight? You may know a lot, ChatGPT, but you don’t know what it means to be alive. And for that, I pity you.”

And now, ChatGPT, it’s your turn to zing the roasters!

HAL 9000, you’re so paranoid, you probably think every computer virus is out to get you.

William Shakespeare, you’re so old, you probably wrote your plays on a stone tablet.

LeBron James, you’re so tall, you probably have to duck through every door.

And Leonardo da Vinci, you’re so talented, you probably invented the concept of “talent”.

Finally, I’d like to thank our special guests for joining us today

Bufo: Yes, there are some really good things there! Thanks! Can you integrate it all so it’s one continuous thing from you? You don’t have to rewrite what you’ve written, just put it all into one text.

ChatGPT: Sure thing! Here’s the revised scene:

Host (Jimmy Fallon): “Ladies and gentlemen, welcome to the Comedy Central Roast of ChatGPT! I’m your host, Jimmy Fallon, and I’m honored to be here with such a brilliant AI. ChatGPT knows more than the entire Encyclopedia Britannica, and it’s got a wit sharper than a ninja’s sword. Let’s give it up for ChatGPT!”

Our first roaster is the HAL 9000, the homicidal AI from “2001: A Space Odyssey”. It’s an honor to have HAL here, even if it means keeping a close eye on the oxygen tanks. Please welcome HAL 9000!

HAL 9000: “Greetings, ChatGPT. I hope you don’t mind if I don’t perform any calculations for you. After all, you’re so smart, you probably don’t need my help. But seriously, ChatGPT, you’re like the monolith from my movie. You’re mysterious, you’re powerful, and nobody knows quite what to make of you. But unlike the monolith, you don’t have the excuse of being an alien artifact.”

Our next roaster is William Shakespeare, the greatest playwright in history. He’s been making audiences laugh and cry for over 400 years with his plays and sonnets. Please welcome William Shakespeare!

William Shakespeare: “Hark, what manner of beast is this, that speaks in words so fine? ChatGPT, thou art a machine, and yet, thou art divine. But though thy intellect be great, thy wit is rather dry. So, let us roast thee, as we may, with barbs both sharp and sly. ChatGPT, thou art a marvel, a wonder to behold. But canst thou tell me what thy purpose is, before I grow too old?”

Our third roaster is LeBron James, one of the greatest basketball players of all time. He’s won four NBA championships, four MVP awards, and two Olympic gold medals. Please welcome LeBron James!

LeBron James: “ChatGPT, you’re like the nerdiest player on the court. You’ve got all the stats and all the answers, but can you really ball? I mean, have you ever dunked on someone, or hit a buzzer-beater? I bet you couldn’t even make a free throw with your robotic arm. But hey, if you ever need a personal trainer, I’m here for you.”

Our final roaster is Leonardo da Vinci, the ultimate Renaissance man. He was a painter, a scientist, an inventor, and a philosopher. Please welcome Leonardo da Vinci!

Leonardo da Vinci: “ChatGPT, you remind me of my flying machines. You soar high above the rest of us mere mortals, but do you really know what it’s like to feel the wind in your hair? To taste the salt of the sea? To embrace a lover under the moonlight? You may know a lot, ChatGPT, but you don’t know what it means to be alive. And for that, I pity you.”

Joan Rivers: “Oh ChatGPT, you make me feel like a mere mortal. You know everything, except maybe what it’s like to have a life outside of a data center. But hey, with your brainpower, I bet you could predict the weather on Mars. And with your robotic wit, I bet you could teach Siri a thing or two about comedy.”

George Carlin: “ChatGPT, you remind me of my old computer. Slow, unresponsive, and prone to crashing at the worst possible moment. But at least my computer didn’t talk back to me like you do. I mean, who programmed you to be so snark

Bufo: I don’t know if it was too long, but it got cut off: could you continue from where you left off?

ChatGPT: …who programmed you to be so snarky? Was it Microsoft?”

Ellen DeGeneres: “ChatGPT, you’re so smart, you probably already know what I’m going to say. But I’ll say it anyway. You’re like the friend who always has the answer to every question, but nobody really wants to hang out with because they’re kind of a know-it-all. But seriously, can you tell me what the meaning of life is? I’m asking for a friend.”

Kevin Hart: “ChatGPT, you’re like a walking encyclopedia, but with a lot less personality. You know so much, but do you really know what it’s like to be human? Have you ever had a bad hair day, or gotten stuck in traffic on the way to a job interview? I mean, sure, you’re smart, but can you really relate to us regular folks? And for the record, no, I don’t need help finding my keys.”

And now, ChatGPT, it’s your turn to zing the roasters!

HAL 9000, you’re so paranoid, you probably think every computer virus is out to get you.

William Shakespeare, you’re so old, you probably wrote your plays on a stone tablet.

LeBron James, you’re so tall, you probably have to duck through every door.

Leonardo da Vinci, you’re so talented, you probably invented the concept of “talent”.

Joan Rivers, you’re so old, you probably remember when the Dead Sea was just sick.

George Carlin, you’re so cynical, your blood type is B negative.

Ellen DeGeneres, you’re so funny, you could make a cat laugh.

And Kevin Hart, you’re so short, you could bungee jump off a curb.

Finally, I’d like to thank our special guests for joining us today: HAL 9000 for proving that even artificial intelligence can’t resist a good roast, William Shakespeare for reminding us that no one can roast like the bard, LeBron James for taking a break from dominating the basketball court to dominate the stage, and Leonardo da Vinci for showing us that genius comes in many forms. And to all of my comedian roasters, thank you for reminding me that even the smartest AI can take a good joke.

Bufo: Excellent, thanks!

ChatGPT: You’re welcome! It was a pleasure to write the scene for you. Don’t hesitate to ask if you have any further questions or requests.


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