Clippy
product on 9 shows · 10 statements across 2 episodes · said 70 times in 11 episodes since 2019
the a16z Podcast 53 
Big Technology 11 
Startups For the Rest of Us 1 
My First Million 1 
the Neon Show 1 
the Startup Ideas Podcast 1 
How I Built This 1 
20VC 1 
the MAD Podcast
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the a16z Podcast 53Big Technology 11How I Built This 1the Startup Ideas Podcast 120VC 1My First Million 1Startups For the Rest of Us 1the Neon Show 1
2025 11 mentions in 2 episodes 6 per episode
2024 4 mentions in 4 episodes 1 per episode
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- every mention in 2024, scene by scene →
2023 2 mentions in 1 episode
2022 1 mention in 1 episode
2021 1 mention in 1 episode
2019 51 mentions in 2 episodes 26 per episode
every mention on every show, scene by scene, with the transcript →
10 statements about Clippy, every show
Pomel: Many big tech AI assistants risk being too much like Clippy
“The risk right now is that a lot of the assistants we're seeing from the big companies are too close to Clippy.”
Sinofsky: About a dozen people worked on Microsoft Clippy
“There were a good dozen people working on this, and I was just one.”
Sinofsky: Clippy had only ~30 animations due to floppy disk space constraints
“Plus we could only have like, you know, 30 different little animations, like types of things like here's waving or smiling or looking, thinking or whatever. And each one can only have a few frames. Right. Because we had to fit on the floppies.”
Sinofsky: Animated UI characters need a framed stage to enter gracefully
“Frank and Ollie were like, you want the box. And we're like, we do. Yeah. They're like, because every character needs a stage. And this allows the character to exit and enter with grace because otherwise it would be like an alien and it would just disappear.”
Sinofsky: BusinessWeek and PC Week gave positive early reviews to Clippy
“Steve Wallstrom from Business Week was like, I was skeptical, but I really liked it a lot. And Peter Coffey at PC Week. Those would be the two mainstream and tech review. Peter Coffey was like, this is a great idea. Like, this makes it easier to use. Yeah. Lik…”
Sinofsky: Microsoft demoted Clippy's interactivity in Office 2000
“So what we ended up doing was, the next release of Office, which became Office 2000, we sort of demoted Clippy, and reduced his interactions, or its interactions, or her interactions some”
Microsoft used costume actors and Flash animations to publicly retire Clippy
“Lisa Gurry on the office marketing team, like, had this, like, let's really go crazy. Yeah. And, like, actually, Like, have a retirement party, and so we went, we flew down to San Francisco, we met with the press to tell them this, and then at one point we jus…”
Sinofsky: Comedian Gilbert Gottfried voiced Clippy in Microsoft promotional blues song
“Gilbert Gottfried, the comedian, was the voice.”
Sinofsky: Publicly retiring Clippy contributed to its cult status
“I honestly believe in hindsight that the, sort of, the boldness of out front retiring him, as opposed to, like, just secretly cutting him and pretending like he never existed. Or it never existed. I keep saying he, but there's no gender. I think that contribut…”