The Life and Death of Microsoft Clippy, the Paper Clip the World Loved to Hate

Before there was Clippy, there was Microsoft Bob.

Personally launched by Bill Gates in 1995, Microsoft Bob was supposed to revolutionize home computing by making software friendlier for first-time users. Instead of the menu- and text-heavy interfaces that had come before, the program transformed the desktop into the virtual interior of a home. To navigate between different applications, users clicked on familiar household objects: a pencil and paper for word processing, an envelope for email, or a checkbook for electronic payments.

Despite its down-home name, Microsoft Bob had been designed to reflect cutting-edge social science research conducted by Stanford professors Clifford Nass and Byron Reeves (who were eventually hired as consultants for the nascent program). In the early 1990s, the pair developed a theory: People unconsciously respond to computers as if they are human. As further tests would reveal, evaluations of a computer’s performance were significantly more positive when people completed them on the machine that was actually running the program. Users who delivered their review on a different computer were more truthful (and therefore more critical)—essentially replicating the level of “politeness” used when evaluating a person to their face, rather than to a peer.

To capitalize on these findings, Microsoft Bob’s developers decided to add anthropomorphic “assistants” to guide users through the program. Ostensibly, these would more concretely embody the the humanity users were already instinctively assigning to their computers.

Microsoft program manager Karen Fries, one of the project’s strongest proponents, had already observed the enthusiasm these digital guides could inspire. During a test session with new PC users, she introduced a prototype cartoon duck that walked participants through the software. “'This guy was very emotional about it,” Fries recalled in a 1995 interview. “He grabbed my arm. He said, ‘Save all the money on the manuals, and just give me this duck to always be there and tell me what to do.’”

And the man got his wish. Microsoft Bob and its suite of animated assistants was released in 1995. There was no manual provided; all learning happened within the program. The default character was a cheerful yellow dog named Rover (“Easy to work with, friendly, helpful. Tries to be your best friend”); other options included a rat named Scuzz (“Couldn’t care less about you. Seldom offers help”). But despite the hype, the program tanked. Tech journalists tore it apart, deriding it for infantilizing new computer users. It was quickly eclipsed by Windows 95, released just seven months later, and discontinued by 1996.

But the assistants—or “Friends of Bob,” as they’d been called—lived on. Their code was translated to the Windows 97 version of Microsoft Office in an attempt to make the increasingly feature-heavy program easier to use. Developers added in several new characters as well: Scribble the cat, William Shakespeare, and—of course—the now-iconic Clippy the paper clip.

Clippy (given name: Clippit) was designed by illustrator Kevan Atteberry, who contributed more than 15 of about 250 potential characters for the new Office Assistants. Although he has said in interviews that focus groups labeled Clippy as the “number one most trustful and engaging and endearing character of them all,” some of Atteberry’s colleagues—including Roz Ho, then an executive at Microsoft—said that Clippy and his compatriots had detractors even before they was shipped.

In fact, there was plenty of discomfort across the board, not just with Clippy. “We did a bunch of focus-group testing, and the results came back kind of negative,” she later recalled. “Most of the women thought the characters were too male and that they were leering at them.” The majority-male leadership team decided to move forward anyway.

Most experts, however, note that Clippy’s real problem was that he was “optimized for first use.” You might appreciate help in writing your very first letter; that exact same offer of help is infuriating by the time you’ve reached your fiftieth. “The reason I think people hate him is not because of what Clippy is, but how Clippy acts,” Atteberry told VICE earlier this year.

Microsoft asked Nass for advice on how to rehabilitate Clippy in 1998. The problem, the Stanford professor said, traced back to his original research with Reeves. If people treated computers in general (and Clippy specifically) in the same way as a person, then both were subject to the same social expectations we have of our peers. “No matter how long users worked with Clippy, he never learned their names or preferences,” Nass wrote in The Man Who Lied to His Laptop, a 2010 book about human-computer relationships. “Indeed, Clippy made it clear he was not at all interested in getting to know them. If you think of Clippy as a person, of course he would evoke hatred and scorn.”

Nass pored through social-science literature to figure out how unpopular people managed to make friends. The answer? Create a scapegoat. He designed an alternate version of Clippy that, if users designated his advice “not helpful,” would encourage them to send a scathing email to Microsoft’s help team. He’d continue to egg them on: “C’mon! You can be tougher than that! Let ’em have it!”

“The results were unanimous,” Nass writes. “People fell in love with the new Clippy.”

Microsoft, unsurprisingly, wasn’t eager for a rogue Clippy to incite the rabble against them. But while Nass’s suggestions were never implemented, the company did begin to poke fun at its most-hated assistant. By 2001, Clippy was no longer a default setting—a decision Microsoft heralded with a short, satirical film in which the annoying paper clip inquires: “Are you writing a letter? Is it a love letter? Can I read it?”

It wasn’t until 2007 that Clippy disappeared entirely. What took so long? James Fallows, a journalist who spent six months working at Microsoft in the late 1990s, noted that Melinda French (then the fiancée of Bill Gates) was the project manager of Microsoft Bob. Although he says Gates would likely have nixed Clippy sooner if the issue had been brought up, it “was a conversation with the boss many people were happy to postpone.”

“The fact that Clippy had been the brainchild of the boss’s wife was mentioned as a little joke, not a seriously decisive factor,” he continues. “But it was a joke everybody knew.”