Tokens & Tactics #20: Turning Comedy Expertise Into an App
Joe Toplyn, four-time Emmy winner and former head writer for Letterman and Leno, on creating Witscript, an AI joke-writing app that performs as well as professional comedy writers.
Welcome back to Tokens & Tactics, our Tuesday series about how people are actually using AI at work.
Each week, we feature one person and their real-world workflow—what tools they use, what they’re building, and what’s working right now. No hype. No vague predictions. Just practical details from the front lines. This week: Joe Toplyn.
Tell us about yourself.
I’m Joe Toplyn, Founder and President of Twenty Lane Media, LLC. My background is in engineering, business, and comedy, an unusual mix that helps me deliver on our mission, “Enhancing the creativity of people and their machines.” Through my company I published my book, “Comedy Writing for Late-Night TV,” and later invented, patented, and launched Witscript, an AI-powered joke-writing app inspired by algorithms in my book.
ChatGPT, Gemini, or Claude?
I tend to stay in the OpenAI family, which has its advantages: I like to think that ChatGPT, because it runs on GPT-5.1, can give me the best insider tips on how to prompt its cousin, the GPT-5 model that powers Witscript.
But I write code for Witscript in Google Colab, where Gemini is available, so I’ll occasionally ask Gemini about Python or some error message. If I weren’t running such a lean operation, I might take the time to explore using Gemini to power Witscript. But perfect can be the enemy of good, and Witscript is already generating great jokes.
What was your last SFW AI conversation?
I’m planning to add a new feature to Witscript and wanted ideas for the name, so I asked ChatGPT. It suggested options in five categories, from “More Branded / Playful” to “More Professional / Analytics-Oriented,” and then recommended one of the names because it’s “immediately understood, friendly, and pairs nicely with your existing features.” I was pleased to see it was the same name I’d already come up with myself.
First "aha!" moment with AI?
A key step in the Witscript joke-generation algorithm is free-associating words that most people think of when they hear a topic. For my test topic, “Arnold Schwarzenegger,” using Word2Vec word embeddings kept giving me dull associations like “bodybuilder” and “governor,” which led to dull jokes. Other approaches didn’t work either. I was stuck. Then in November 2021 I got approval to use Open AI’s GPT-3. It generated exactly what I needed, associations like “The Terminator” and “I’ll be back.” Aha! So I started replacing big blocks of Python code with calls to GPT-3.
Your AI subscriptions and rough monthly spend?
I don’t pay for any AI subscriptions; I use the free versions of ChatGPT and Google Gemini. The variable cost for Witscript to use the OpenAI API is still less than $50 a month.
Who do you read/listen to to stay current on AI?
I listen to the Everyday AI Podcast, hosted by Jordan Wilson. It tells me what I need to know.
Your most-used GPT/Project/Gem?
I generate jokes with Witscript almost every day. You input a topic sentence, like an utterance in a conversation, and it uses the GPT model and my humor algorithms to return a funny response. The app is for anybody who needs jokes–marketers, content providers, standup comics–but doesn’t have the time or skill to write them or the money to buy them.
The AI task that would've seemed like magic two years ago but now feels routine?
Until recently, most researchers believed that creating and recognizing jokes was a uniquely human trait and therefore a holy grail of AI. Now Witscript is cracking jokes that get as much laughter as jokes written by a professional comedy writer; check out this paper.
Have you tried full self-driving yet?
No, I haven’t had any experience with self-driving.
Latest AI rabbit hole?
I’ve often spent hours tweaking a prompt for Witscript, frustrated when an input isn’t giving me quite the output I want. But the process is worth it, because success means I laugh.
One piece of advice for folks wanting to get deeper into AI?
Beware of “Shiny AI Syndrome,” the tendency to get distracted by the latest buzzy AI tool. Just pick a tool you’ve heard good things about and build something with it. And have fun!
Who do you want to read a Tokens & Tactics interview from?
PR and marketing exec, and AI comedy practitioner, Eric Doyle.
If you have any questions, please be in touch.
Thanks for reading,
Noah and Claire
Witscript is like a human comedy writer that never insists "it'll kill... eventually."