When Office XP launched in about 2001 Microsoft had a comedy microsite all about Clippy being forced to retire (the angle being that XP was so easy to use he was no longer needed). It was entirely based around the idea that everyone was sick of clippy.

They had a couple of flash animations (the contemporary equivalent of a viral video), recorded here for posterity. Clippy was voiced by Gilbert Gottfried

Part 1: https://www.youtube.com/watch?v=tu_Pzuwy-JY

Part 2: https://www.youtube.com/watch?v=82KZG3Zy8xU

Part 3: https://www.youtube.com/watch?v=sAsV6_AawVw

Remains of microsite here: https://web.archive.org/web/20031009044305/http://www.micros...

There was also a downloadable blues-type song which was titled 'it looks like you're writing a letter', I can't find it anywhere now but it was pretty good

edit: found the song! its at 1:01:35 in this video: https://youtu.be/8bhjNvSSuLM?t=3690

Microsoft really missed an opportunity to bring back clippy when showing chat gpt integration in office/windows.

It has deep nostalgia to a generation of computer users who are non-technical. People that were annoyed by it were either power users who wanted the machine to get out of their way, or learners who didn’t find it helpful.

I think in this case it would have worked much better and simultaneously validated earlier failed ideas. They would be viewed as ahead of their time, not like wrong futures.

Imagine the Microsoft press conference moment where clippy pops up and ACTUALLY HELPS YOU. I’d probably cry a little.

So Clippy came from Microsoft Bob. Microsoft Bob itself was a response to General Magic's "social interface", known as Magic Cap [1].

Another thing that came as a response to General Magic: Java. Java was a response to General Magic's Telescript [2].

So Clippy and Java were both inspired by the same product!

Watch the video [3] for an important piece of history!

[1] https://en.wikipedia.org/wiki/General_Magic#Magic_Cap

[2] https://en.wikipedia.org/wiki/General_Magic#Telescript

[3] https://youtu.be/7PpTVrWSMlY?t=63

Plagiarizing a comment of mine from another post:

In general, cutesy UIs are fun only the very first time you use them. But they’re a liability in the long term because once the novelty of the cuteness wears off, you risk really annoying your users, especially in high-stress scenarios.

Expanding on that: Clippy is endearing now because it hasn't annoyed anyone for a decade+, but it was a real nuisance — difficult to disable and not nearly useful enough to justify its incessant interrupting.

Avoid cutesy UIs.

The real interesting part about Clippy is not the cartoony art, but the fact that it actually would have been helpful if the project managers of office would not have gutted it: http://erichorvitz.com/lum.htm

Microsoft was already into drawn characters a few years earlier.

Microsoft Comic Chat[1] was their take on how IRC should look like. It was quite popular for a short time and a bit annoying for users with other IRC clients. MS Comic Chat user sessions would send public messages upon joining channels: "# Appears as ANNA".

https://en.wikipedia.org/wiki/Microsoft_Comic_Chat

I always thought the idea was ambitious and interesting.

The biggest problem, as he points out, was that it was a bit too simplistic. Anyone who was anywhere near to being a power user with work to get done was mostly going to be frustrated by it.

It was cute - even delightful - to me at first, then quickly just got in the way. To my mind, two things which could make such an idea more successful would be 1) making it easier to deactivate, and 2) having a more robust 'advanced' mode which points you to actual documentation, articles and support forums and other than that leaves you alone. I don't think the tech for that second part was possible back then (especially parsing natural language inquiries), but it is now.

The characters I ended up using most were the little dog and the bouncing ball. I didn't mind Clippy, but after seeing how others reacted to him I didn't want people to know that. The animations were great for all of them regardless, there was clearly a lot of talent deployed there. Unfortunately that has almost no connection to usefulness.

Clippy wasn’t as bad as the ribbon.

Because there's seemingly a "totoro tuesday" for everything. There's even notes about Japan-only releases of windows. Neat.

https://www.instagram.com/p/CTgYYqZBoP2/?utm_source=ig_web_c...

Was clippy that bad or is it something we just love to hate or pile on, but much like Nickelback, who cares, it’s easy to ignore / disable in clippy’s case? I really don’t remember as I was a teen when clippy came out. I liked the Merlin version fwiw.

I'm going to say it: I loved clippy.

I loved it so much that in 2005 for my CompSci final project I created a search assistant, using the agent builder tool, C# and the Google API.

I think it should come back as a personal AI agent.

I would not really consider the illustrator being its "creator". Sure the illustration is an important part but the real interesting questions would probably be answered by its product manager.

am I the only one who remembers that his name was "Clippit"?

Clippy as a virtual assistant power by AI would work.

Funny story.

In the same way, I really dislike using references to popular movies or characters in code samples or sample projects, esp. if it is the official docs for a framework or something similar.

I see a ton of "battle of superheroes" kinds of apps that try to demonstrate cool stuff, like deploying distributed applications over multiple clouds/k8s distributions, using serverless, Istio, and who knows what. But I just can't get over the fact that such tutorials are not made for me, as I've not watched any superhero movie since I was ~10 years old.

I don't think cuteness anything to do with it.

It's when style interferes with the functionality, that people start to get annoyed. But that applies to any aspect really: Animations, Minimalism / Skeuomorphism, Simplicity / Complexity...

Many apps successfully introduce cuteness through iconography and illustrations. Eg. Duolingo, Bear Notes, TunnelBear. Also look at Panic who have a (very mild) playful aesthetic in their power-user development tools: https://nova.app

Cutesy stuff is mostly just a culturally dependent thing, our appetite in the U.S. seems rather low whereas sensibilities in Japan and maybe East Asia in general are much higher. But really, in my opinion, if you're going to do something cute in a UI, the most important thing is to treat it like art rather than directly as means to accomplish some "business" end like appealing to a demographic or worse, for emotional manipulation. It's best if it's done to authentically make something pleasant and comfortable, rather than to check some weird boxes from the higher ups. Otherwise, it's going to feel immensely fake, and fire off the bullshit alarm of a large population of people.

Let's not forget we're talking about the 90's Microsoft. Cute or not they were bad at UI/UX, so bad that no guideline would help them.

Doubly so with cutesy “aw shucks” error messages.

Never put a pun in a UI