Mike Stone has some thoughts on the late, not-much-lamented Clippy:
For those that don't know, Clippy was the default avatar for the Microsoft Office Assistant in Office 97 to 2003. The actual name was Clippit, but if you point that out, most people won't know or care.
Now, to be fair, the Office Assistant was terrible. It was so terrible that Microsoft even spoofed firing it in an ad campaign.
I draw a line between Clippy itself and the Microsoft Assistant, and try to look at what was intended with Clippy instead of how the botched implementation really set back computer-based assistants for a long time.
I remember the Microsoft Office Assistant from Office 97 through to 2003. In retrospect, having Clippy be the default avatar probably didn't help the image of the Assistant feature, and most people never seemed to work out that other options were available. Personally, my favourites were Scribble the cat (from Office 97), and Lynx the cat from Office 2000.
So, what was the intent of Clippy?
The idea here was to have an assistant that anticipated your needs and assisted you in your work. The theory behind it really isn't all that different from voice assistants we have now, like Alexa, Siri, and the Google Assistant. It just pre-dated them by more than a decade and wasn't voice driven.
I honestly think there's room for a new “version” of a desktop assistant like Clippy on the modern desktop.
Now, before I get bombed from orbit, I realize that individual workflows vary significantly. How someone using a Mac works is significantly different from someone running i3 on Arch, so when I say that there's room for a version of a desktop assistant like Clippy on the modern desktop, I don't mean that to be for everybody.
I'm more talking about something like a less crappy version of the Bonzi Buddy. Perhaps a graphical front end for Mycroft that was more interactive and had the capability of anticipating your actual needs.
I could definitely see a use for an on-screen assistant as an option for those new to Windows / macOS / Linux / whatever, or people with disabilities. One thing I've noticed lately is that, for all their advances, modern operating systems pretty much expect you to know roughly what you're doing and don't think to ask "do you need some guidance to get started?" Actual paper manuals are long gone, and how-to or for-dummies guides are an additional purchase.