When a large company stumbles, it’s major news. Coca-Cola infamously angered millions of soda drinkers when it tinkered with its recipe to produce New Coke in 1985. Netflix may now be the country’s biggest single source of entertainment, but it wasn’t long ago they tried to spin off their DVD and streaming services into separate entities, confusing millions of otherwise satisfied consumers.

Stationed somewhere in between those gaffes sits Clippy, the unofficial name for the bouncing, sentient paper clip introduced by Microsoft in 1996 in a bid to help people hone their word processing skills. When Microsoft Office software users began writing a letter by typing “Dear,” for example, out would pop Clippy with an unsolicited offer to help.

The first time this happened, users may have been amused. But as they grew more proficient, Clippy would redouble his efforts to interrupt, his roving eyes scanning documents in what felt like a gross invasion of privacy. In no time at all, he would be the subject of scorn and ridicule, an ever-present voyeur into your home computer navigation.

In order for Microsoft to continue to flourish, Clippy would have to die.

Blame It On Bob

In the 1990s, Microsoft had already revolutionized personal computing with its Windows interface. Taking navigation out of its sterile DOS command prompts and making it feel more like the welcoming layout of Apple’s Macintosh line, Windows helped facilitate the PC boom.

The company wanted to take it one step further with Bob, an operating system programmed to resemble the rooms of a house. Going to the “checkbook” on the desk, for example, would open financial software. Released in 1995, the virtual domain never took off, with users and industry observers declaring it so purposely cute that it was nauseating. (Even worse, the hated typeface Comic Sans was created for use in Bob, perpetuating a cycle of user cruelty.)

Although Microsoft quickly abandoned Bob, it seemed stuck on one of the characters that populated the OS: Clippit, an energetic paper clip that injected itself into tasks to see if it could make the experience easier on users. According to Clippit illustrator Kevan Atteberry, Microsoft had developed over 250 characters for such a purpose: Clippit, which users later re-named “Clippy,” won out, and the company decided to keep him around for the 1996 release of its word processing software.

Despite Microsoft harnessing the knowledge of social psychologists from Stanford to develop these software assistants, there were early signs Clippy was destined to annoy users. Focus groups exposed to the character made frequent references to his “leering” eyes, which product testers found particularly unsettling.

Failing to heed their criticism, Microsoft inserted Clippy into the version of Office released in 1996. Users opening a blank document were greeted by a jovial paper clip that offered advice on everything from spelling to saving files. Even if keyboard shortcuts and other operating commands were mastered, Clippy materialized from the ether, repeating himself until they could figure out how to shut him up for good. (For Office 1997 users, that meant manually changing his program folder name from “Actors” to “NoActors.”)

An Uninvited Guest

Although Clippy received the brunt of criticism, he wasn’t the only Office mascot available to distract and annoy. The Genius was an Einstein-esque icon; Power Pup was a dog that could help you retrieve information. But Clippy was the pre-set helper, and his wiggling eyebrows and contorted paper clip frame burrowed into Windows users’ psyches.

Microsoft was not insulated from the Clippy criticism. Writing of his time working for the company, James Fallows reported for The Atlantic in 2008 that the excitable little stationery accessory was bemoaned by employees. Yet Clippy remained, getting a minor makeover in Office 2000 before being automatically turned off in 2002. (Microsoft poked fun at the user enmity, announcing the character was out of work and creating a game that allowed players to zap Clippy with a staple gun.)

Why the allegiance? Fallows said it was in part related to Clippy’s origin as a resident of the failed Bob operating system. That project was spearheaded by Melinda French, who later became Melinda French Gates, wife of Microsoft founder Bill Gates (and still later became the ex-wife of Bill Gates, following their 2021 divorce). While Fallows is quick to point out that it wasn’t the sole reason Clippy remained an uninvited guest, no one was particularly enthusiastic about getting rid of him, either.

Clippy eventually met his end in 2007, when the latest version of Office shipped without his grating interjections. Distanced from the pain of actually having to deal with him, a number of Clippy’s critics began to produce damning fan art, from Clippy being a general nuisance to engaging in lewd acts. In 2015, author Leonard Delaney self-published Conquered by Clippy, a 16-page erotic short story that was either a meditation on how technology is seducing us or just a weird story about a paper clip copulating with a human. (Delaney also penned Taken by Tetris Blocks.)

And yet this was not the end of Clippy. In 2017, an anonymous programmer offered a Chrome extension that allowed Clippy to pop up virtually everywhere you go. In 2021, Microsoft hosted a Twitter poll that invited people to like a Clippy Tweet. If it got 20,000 likes, the company promised to replace its paper clip emoji in Microsoft 365 with Clippy. The clip also surfaced as a sticker set in a 2021 update of Microsoft Teams. Like the original, all of them are basically useless.

A version of this story ran in 2017; it has been updated for 2023.

This article was originally published on www.mentalfloss.com as The Tragic Life of Clippy, the World's Most Hated Virtual Assistant.