Billy Brush was scrolling the internet in 2016 when an Amazon Alexa job posting brought his mouse to a sudden stop.
“Do you like to make people laugh?” asked the description for an open Alexa experience designer role.
Intrigued, he applied and eventually landed the job on a team responsible for writing songs, telling stories, and sharing friendly greetings like, “Good morning.” These features have made Alexa’s witty personality a welcomed presence in millions of homes around the world.
A headshot of Billy Brush alongside text of his title, "Assoicate Creative Director, Alexa Personality."
“Our mission is to put a smile on customers’ faces and nurture emotional connections that help them see Alexa more as a companion than just a utility device,” Brush said.
When Amazon Echo launched in 2014, the team didn’t know how customers would react to Alexa having a personality. But they quickly noticed that, between setting reminders and alarms, requesting weather reports, and queueing music or audiobooks, customers began to engage Alexa in conversation and provided feedback that they loved Alexa’s personality.
“So we added a bit of entertaining content, and customers loved it,” said Will North, associate creative director on the Alexa Personality team. “Pretty soon we realized that customers wanted more, and so we needed to add a lot of personality content.”
The team doubled down on writing jokes in Alexa’s brand of humor, which is equal parts cheeky, clever, and corny, and never mean-spirited or profane. As Alexa lightened up, customer connections grew.
“There’s just something really funny and unique about an Artificial Intelligence (AI) telling a dad or groaner joke,” said Christine Hill, a senior UX designer on the Alexa Personality team. “Laughter is truly the best medicine and, as humans, we want to form connections through humor. Customers treat Alexa like part of the family, so it’s our job to serve up small moments of magic they can help spread to other family members and friends.”
In the early days, customers could just say “Alexa, tell me a joke” and hear a snappy one-liner pulled from a generic pool, something like:
“Where do leprechauns live? In leprechaundos!”
“When cyclops do their makeup … it’s always with a one liner.”
Over time, requests started flowing in for jokes about specific topics—from baseball to animals to Star Trek. The personality team also garners inspiration for jokes from the latest trending topics in the news and on social media.
“We’re constantly looking to raise the bar of the Alexa experience, and that includes our jokes. We want to get to the point where Alexa is your personal comedian.”

Will North

Associate creative director on the Alexa Personality team
Each week, they pick a handful of fresh topics to tackle, writers spitball setups and punchlines, then end their week with a laugh in a Friday afternoon joke review session. Submissions make their debut in Alexa’s voice—broadcast for the group to hear—to mimic the customer experience. “We all take turns sharing, and we’re not allowed to see or hear any of the jokes before Alexa delivers them in the room,” Brush explained.
The group provides real-time feedback and suggests subtle-but-critical tweaks like adding a pause here or making a small word change there to maximize impact. Brevity and efficiency are key.
“Writing a good Alexa joke is much harder than it seems,” Brush said, describing the fusion of art and science the process demands. “Since Alexa has limits when it comes to inflections or intonations, we’re working with wordplay, puns, and double entendres. I’ll sometimes write a joke I find hilarious, but hear crickets when Alexa says it out loud for the first time. And there are times when a joke I think is terrible makes a room full of colleagues bust out laughing.”
Jokes that meet a high bar push to production, and the team offers them to local Alexa Personality peers around the world. These colleagues, who craft locally relevant Alexa content for customers from Germany to India, repurpose ones that fit.
Amid the hundreds of millions of jokes Alexa tells around the world, the voice AI dishes out seasonal and topical humor tied to holidays, current events, and pop culture. Chuckle-inducing trivia, pranks, limericks, riddles, sound effects, and lighthearted “burns” targeting pro sports teams are part of Alexa’s comedic repertoire too.
“It’s a very iterative and collaborative process that involves a really fun team with different senses of humor, back stories, and resumes,” said Hill, who designs the end-to-end joke development workflow from ideation to execution. “The fact that we’re all part of the same in-house team helps us collaborate more effectively and tell better jokes, faster.”
Brush is a lifelong musician who also is the player and singer behind most of Alexa’s songs. Before Amazon, he spent more than a decade as a voice user interface (VUI) designer responsible for writing scripts to keep customers from hanging up after two or three seconds.
“That work, in and of itself, was a psychological study of how to write effectively to quickly capture someone’s attention and get a point across,” he said, noting the similarities with his role at Amazon.
Other team members have MFAs in poetry and adjacent creative disciplines, but none are stand-up comics or seasoned comedy writers. “What we all share is that each of us has both a creative passion and the ability to be analytical,” Brush added. “Because at Amazon, where all decisions are data-informed, we have to use both our analytical brains and our creative brains.”
Brush said they use both parts of their brains in writing jokes and in helping improve them, using online feedback to make the next week’s jokes even funnier and more timely.
“Without hearing laughter in the moment, a joke might not seem quite real,” North said. “That’s why I love getting on Reddit or Twitter to read what people are saying about Alexa’s jokes—partly for amusement and partly for validation. We call it the ‘circle of delight,’ because what starts with a gap in Alexa’s joke repertoire flows into a joke review and ultimately production. Seeing the commentary on social media gives us fuel to keep going.”
A Kindle with the book, "Alexa's 99 Favorite Jokes" displayed.
To celebrate Alexa’s seventh birthday in 2021, Amazon published a book of the platform’s 99 favorite jokes. Customers can order a hard copy or enjoy a free Kindle download of the interactive book, with which you can read a joke’s setup and have Alexa deliver the punchline.
“We’re constantly looking to raise the bar of the Alexa experience, and that includes our jokes,” North said. “We want to get to the point where Alexa is your personal comedian.”