How Microsoft’s Clippy went from hated assistant to beloved icon

For computer users of a certain age, the name “Clippy” is infamous. You remember who he is: The onscreen assistant from Microsoft Office products in the late ’90s and early 2000s. Clippy (originally dubbed Clippit), so-named because he’s an anthropomorphized paperclip, would pop up onscreen to offer suggestions and tutorials. But 99.9 percent of the time his presence was hugely annoying, and his advice was completely off-base.

A curious thing has happened in the 20 years since Clippy’s debut, though. Clippy isn’t hated anymore. In fact, you might even say he’s adored.

Take, for example, a moment from Microsoft’s BUILD conference this year. Press swarmed to take pictures of and with a “real life” Clippy.

Clippy has evolved in our hearts and minds, and now it holds a firm place in the land of nostalgia.

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The early days of Clippy

Clippy’s beginning wasn’t that rosy, even at Microsoft. James Fallows, a former Microsoft Word team member, shared his view after working in Building 17 on Microsoft’s campus for six months:

“Very few people I ran into at Microsoft thought that Clippy was such a great idea…Clippy suffered the dreaded ‘optimization for first time use’ problem. That is, the very first time you were composing a letter with Word, you might possibly be grateful for advice about how to use various letter-formatting features. The next billion times you typed ‘Dear …’ and saw Clippy pop up, you wanted to scream.”

Before the overly zealous digital assistant even shipped in Microsoft Office, focus groups foretold his dismal future. Roz Ho, an executive at Microsoft at the time, said that in focus group testing, the results came back “kind of negative.” Women, in particular, didn’t like him: They thought he was “leering” at them. (The male engineers behind Clippy brushed off the focus group results and shipped Clippy not long after, leering eyes and all.)

Even Clippy’s designer was reticent to acknowledge he was behind the icon for a time.

“When I first designed Clippy—after I designed him and left the project—I didn’t put him in my portfolio or résumé, because I knew how people reacted to him. They hated him,” illustrator Kevan Atteberry told Motherboard in an April interview.

Finally, when then Microsoft CEO Bill Gates announced Clippy’s retirement in 2001, saying “XP stands for Ex-Paperclip,” he got a standing ovation.

In 2010, Time listed Clippy as one of the 50 worst inventions of all time.

Clippy’s resurgence

Today, Microsoft’s infamous virtual assistant is more beloved than hated. It only took 20 years—or perhaps, a little less than that.

Personally, I hadn’t really given Clippy much thought for about a decade, until early 2014. One of my colleagues created, and then subsequently convinced hundreds of Twitter users, to follow a parody Clippy account, @ClippyTheClip. (Three years later, this account still has more than 1,900 followers.) The stunt worked so well that even Satya Nadella, then the brand-new CEO of Microsoft, chimed in on Twitter. Clippy, so creepy, awkward, and annoying as a Microsoft Office tool, somehow made perfect sense as a popular Twitter personality.

This year, Clippy began recirculating into the internet vernacular. In March, Clippy returned via a Chrome extension called “Clippy Everywhere!” Once installed, the animated helper pops up to offer “assistance” in your web browsing. In actuality, that’s all the extension does: He doesn’t offer any real utility or help at all. The paperclip just sits in the corner of your webpage, creeping at you with those vaguely disembodied eyes.

A month later, an even less useful iteration of Clippy arrived. An artist created a truly disturbing yet hilarious rendition of Clippy as…pregnant.

Dubbed “mpreg” Clippy, it flew around the Twittersphere. Clippy’s original creator even joined the conversation. Clippy was back.

The unlikely future of Clippy

We could chalk up our change in opinion about Clippy to something modern internet culture is well versed in: nostalgia. Once thought of as a mental disorder, nostalgia can paint the past in a warmer hue as our brains distort and idealize what actually happened, psychologist Neel Burton explains. The bad or boring bits fade from memory more quickly than the more positive peak experiences. (This explains so much about so many of my more questionable life decisions).

Today, personal digital assistants are a part of our daily lives. On our phones, we have Siri and Google’s Assistant to answer our questions. In the home, there’s Alexa. Hundreds of apps are imbued with some degree of artificial intelligence so they can predict what information you may need next or what content you’d most like to see in your social media feed. Now, we can look back at Clippy as an early predecessor to these systems. It paints his un-helpfulness in a different light: He’s not so much annoying as just a fumbling, crawling toddler version of modern virtual assistants.

“We look back fondly on Clippy because it shows us how far we’ve come since those days, both as a society and as an individual,” Burton said via email. “Now we celebrate him because he’s cute and a bit hopeless, and emblematic of a time when IT was simpler, more controllable, less frightening. He acts as a portal for taking us back to those times.”

With Clippy’s newfound status as a beloved icon, though, is it possible that we’ve reached a point where Clippy could make an actual resurgence?

It’s not likely. Microsoft has placed its digital assistant cards in Cortana, the disembodied AI built into recent versions of Windows (and more recently, on iOS and Android phones). Perhaps, however, we’ll continue to see Clippy crop up at Microsoft events to drum up attendee enthusiasm. And perhaps, most importantly, its creators can finally rest easy. They’re not responsible for a monster anymore. They’re responsible for an icon.

“I am not put off by people hating him,” Clippy illustrator Atteberry says now. “The fact that people know who he is is the important thing to me. That he’s still part of our culture…even though he hasn’t been part of the software in decades.”

Christina Bonnington

Christina Bonnington

Christina Bonnington is a tech reporter who specializes in consumer gadgets, apps, and the trends shaping the technology industry. Her work has also appeared in Gizmodo, Wired, Refinery29, Slate, Bicycling, and Outside Magazine. She is based in the San Francisco Bay Area and has a background in electrical engineering.