Sunday Long Read: Clip Joint

Our Sunday Long Read this week is Benjamin Cassidy's piece in Seattle Met on the history of everyone's favorite -- and reviled -- Microsoft digital assistant/mascot, Clippy the Paper Clip.

THE BLANK SCREEN was already intimidating enough. Then, out of nowhere, an incorporeal know-it-all popped up to make us feel even worse about the novel notion of word processing in the mid-’90s. “It looks like you’re writing a letter,” a googly-eyed, caterpillar-browed paperclip in Microsoft Word observed when we may or may not have been trying to write a letter. The metallic office supply bounced around the margins of documents and never stopped looking over our shoulders, even as it blinked back at us impatiently. “Would you like help?”

Many users found its polite but presumptuous suggestions invasive, obnoxious, and creepy. Almost immediately, computer geeks and neophytes panned it. Microsoft banished it. Time labeled it one of the 50 worst inventions ever. But nearly three decades after its genesis at the Redmond tech giant, Clippit—better known as Clippy—improbably lives on.

Last year, Microsoft officially revived the Office Assistant that debuted in Office 97. The character replaced a plain old paperclip in Microsoft 365 to help liven up the company’s emojis and indulge a social media outpouring. Clippy can now permanently live in Word files, Outlook emails, or other common workplace apps. In one of the company’s Teams backgrounds, the paperclip hovers above yellow legal pad paper on a pedestal in a cement-walled basement, seemingly exiled to the dungeon of bad tech ideas.

Though coding circles treated Clippy like New Coke, pop culture never quite quit the retired paperclip. When Darryl Philbin needed help with a resume in the season seven finale of The Office, he pined for Clippy. When users couldn’t grasp Pied Piper’s platform in Silicon Valley, the startup begrudgingly turned to a virtual assistant named “Pipey.” When Seth Meyers needed a dash of comic relief amid news that a PowerPoint may have spurred the Capitol insurrection last year, he joked Congress would “have to subpoena Clippy.” Saturday Night Live nodded to this nagging cultural endurance in a sketch six years earlier. As J.K. Simmons tries to type a letter to a friend on Microsoft Word, a shimmying push pin, “Pushie,” prods him with suggestions. Then Simmons’s character discovers a “Murder Pushie” option. Yet, the actor can’t bring himself to click it.

Nerd culture’s attachment to Clippy is even stronger, manifesting most frequently on social media and dark corners of the internet. An erotic short story, “Conquered by Clippy,” reveals perhaps the wildest level of obsession (“‘assist me deeper’”). Viral fan art renders the sentient silver fastener as everything from mildly impressed to pregnant. The assistant’s once-grating command bubble and syntax is basically Mad Libs for passive aggressive memes, including those aimed at the sort of existential conundrums posed by tech today. “It looks like you’re writing unsubstantiated nonsense,” a popular one begins. “Would you like to turn on all-caps?”

These days, an annoying Word creature might seem eminently tolerable compared to the ghouls on Twitter. Now that Alexa’s in our bedroom and Siri’s in our hand, Clippy’s a throwback to what seems like a more benign digital age.

But to those involved, directly and indirectly, with what’s been called one of the worst user interface rollouts in tech history, Clippy’s comeback is varying degrees of bewildering and vindicating. Especially after what happened to Bob.

 

I know I grew up with Clippy in college and later in my first tech support job. People either thought Clippy was great, or like me, that it was the bane of existence and that it needed to burn in hell. Either way, Clippy is back for a new generation, for better or for worse.