this post was submitted on 15 Aug 2025
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Nobody thinks Clippy was good, and that's the point. In the original video Louis Rossmann does talk about Microsoft's shenanigans with IE at the time.
The point is that Clippy was widely considered to be bad, and everyone considered Microsoft to be bad at the time, but everything involving technology has become so much worse since. Microsoft would be considered the most ethical tech company in the world if they still operated the way they did in the 90s. It's not the Microsoft was good in the 90s (far from it!) it's that Microsoft and all of the other tech companies have gotten so much worse since then.
The clippy thing is kinda genius really. We've been boiling the frog on a lot of things and we don't really think about how much worse things are now than they used to be. People in positions of power now probably did encounter Clippy when they were younger. Reminding them about how annoying Clippy was may make them realize how much more annoying they're being when making decisions about technology.
I hate clippy. As a millennial who did use the version of MS office (briefly anyway) that had clippy I did get a bit of nostalgia and I installed a VM of windows 95 and installed the version of office with clippy in it.
Then... I instantly remembered WHY I hated him. The reason is that when he pops up to offer you useless advice, he fully takes control and interrupts your work and you have to dismiss him to continue what you were doing. He does it often, too.