The Tragic Life of Clippy, the World's Most Hated Virtual Assistant

Microsoft
Microsoft

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.

A screen shot featuring Clippy
The Science Elf, YouTube

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 female product testers found particularly unsettling. (Though he lacked any genitalia, Clippy was labeled male by Microsoft.)

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.")

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.

Clippy meets his maker
Stan Honda/Getty Images

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. 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.)

Clippy’s final bow—for now, at least—came earlier in 2017, when an anonymous programmer offered a Chrome extension that allows Clippy to pop up virtually everywhere you go. Like the original, he’s basically useless.

Too Sexy to Last: The Right Said Fred Story

Ralph Orlowski, Getty Images
Ralph Orlowski, Getty Images

Guy Holmes popped the tape into the cassette player in his car and waited. The British record promoter was eager to hear new acts, but knew that the majority of them weren’t going to be good or unique enough to cut through the noise of the worldwide music scene. In 1991, it was still a multibillion dollar business, not yet smothered by file-sharing. Success was determined by decision-makers at record labels and radio stations, whose tastes were often mercurial and hard to anticipate.

The cassette had been given to Holmes by a friend, a 19-year-old named Tamzin Aronowitz. She was dating Rob Manzoli, the guitarist of an act called Right Said Fred, and insisted the group—which also consisted of brothers Richard and Fred Fairbrass—had a hook. He listened.

I’m too sexy for my car

Too sexy for my car

Too sexy by far

And I’m too sexy for my hat

Too sexy for my hat

What do you think about that?

Holmes was driving with a friend, a man of Russian descent who had been drinking vodka for most of the night. As Richard Fairbrass sang about other things he was too sexy for—Milan, Japan, parties, his shirt—Holmes noticed his passenger bouncing in his seat and mouthing the words.

This might be a dumb song, Holmes thought. A very dumb song. But it’s catchy.

By 1992, “I’m Too Sexy” was the number one tune in 32 countries, including the United States, and the Fairbrass brothers went from being gym managers and sporadic musicians to the kitschy pop act of the moment. But they wondered whether people knew they were in on the joke, and whether they had the ability to survive the plague that had taken down so many talented musicians before them—the affliction of being an overnight success.

 
 

Richard Fairbrass was born in East Grinstead, Sussex in 1953. His brother, Fred, followed three years later. Raised in a relatively well-off environment by Peter and Mary Fairbrass, Richard thought he might wind up becoming a politician; Fred was more interested in athletics. By their late teens, both had gravitated toward music, forgoing any thought of a formal career in exchange for odd jobs and band practice that led to small gigs with London punk bands. At one performance, an irate—or possibly enthused—fan managed to pee on Richard.

From 1977 to 1987, they performed under a variety of names, including Trash Flash and Money, and landed a series of not-quite-breakthrough gigs. Richard got a job as a session musician for three David Bowie music videos, while Fred had a stint backing up Bob Dylan. Their act wavered from punk to rock to a blend of the two.

After an unsuccessful tour of New York, the brothers returned to London in 1988. Both took to going to the gym to build their bodies back up and shaved their heads. They also met Rob Manzoli, a guitarist, and Brian Pugsley, who had access to computer synthesizers that the brothers thought might evolve their sound into something more palatable than their acoustic act.

Jamming in Pugsley’s apartment one night over a bass line inspired by Jimi Hendrix, Richard took off his shirt—it was hot in there—and proclaimed he was “too sexy” for it. From that line evolved an entire hook that played on the narcissism the brothers had witnessed both in the gym and among the models in New York’s fashion scene. The song wasn’t about the band thinking they were too sexy, but about the self-absorbed egos who really believed it. Supported by a backing track from a DJ named Tommy D, "I'm Too Sexy" was polished into an anthem about vanity.

 
 

Now going by Right Said Fred—a name they took from a 1962 Bernard Cribbins song about furniture movers—the trio started shopping the single to record labels. No one was interested. The only bite was from Holmes, who tried to entice executives but was met with the same resistance. In a self-admitted act of “belligerence,” Holmes produced copies of the single himself, while his secretary, Aronowitz, became the group’s manager. It was a homegrown operation, one in which the group was urged to formally record the final version of the song in an unheated studio because it was cheaper.

“I’m Too Sexy” made its way into the hands of producers at the BBC and Capital Radio. “I’m not sure if this is good or it’s crap,” one radio producer said, then played it anyway. The song spread quickly, making its way to the top of the most-requested queues in England. A DJ from Miami was on vacation in Europe when he heard it. From there, it spread to the United States and abroad, topping the Billboard Top 100 chart for three weeks straight and becoming a perpetual club selection well into 1992. (It only rose to number two in the UK, trumped by Bryan Adams’s “(Everything I Do) I Do It For You.”) The pop icon of the era, Madonna, announced she was sexually interested in Fred. Truant students announced they were “too sexy” for school. Stewardesses asked the brothers if they weren’t “too sexy” to be on a plane, a variation on a joke that they would wind up hearing thousands of times.

“It’s part of the job,” Fred said of the jokes.

Almost immediately, Right Said Fred underwent what industry veterans would call an "image makeover." A fashion designer squeezed them into vinyl outfits, fishnet shirts, and various half-clothed stage uniforms. Though they were in their early thirties, they fibbed and told reporters they were in their early twenties. They were advised to ease up on the weightlifting, as their pumped-up physiques were deemed too frightening for general public consumption.

Holmes produced their first album, 1992's Up, and helped them spin off two more successful songs: “Don’t Talk Just Kiss” and “Deeply Dippy.” They made the requisite MTV appearances and fended off speculation that “I’m Too Sexy” was a sign of them being the prototypical one-hit wonder.

Unfortunately, "I'm Too Sexy" wound up proving exactly that. But the brothers would argue that it was not their fault—it was Holmes’s.

 
 

Up had taken just five weeks to record. Their sophomore album, Sex and Travel, took nine months. Released in 1993, it failed to capture the public’s attention in the way “I’m Too Sexy” seemed to reverberate with kids, teens, and adults.

The brothers would later point the finger at Holmes, claiming he had chosen to release the wrong single tracks; Holmes countered that Richard and Fred had final say over what got the “A” side of the records. Subsequent albums followed—nine in all—but none ever reached the heights of their event-filled summer of 1991.

“I’m Too Sexy” remains a popular jab at people who indulge in vanity, and the brothers still perform it as part of their regular gigs. (Manzoli left the band in the mid-1990s.) They approved a new version targeting Syrian president Bashar al-Assad (who was revealed to have had the song on his playlist) and debuted it on Last Week Tonight with John Oliver in 2014. (“I’m too sexy for this shirt” became “You’re too awful for this Earth.”) To this day, however, Fred believes there’s still some confusion over whether the song is to be taken seriously. He tried to clarify it for Rolling Stone in 2017.

“They didn’t get the cynicism and the joke,” he said. “But the idea of the song is that you obviously can’t be too sexy, right? No one can be too sexy.”

Bottle Service: How Snapple Took Over the 1990s

David Paul Morris, Getty Images
David Paul Morris, Getty Images

For many consumer brands, the ultimate sign of success is being the subject of an urban legend. In 1985, Procter & Gamble had to refute accusations that their moon and stars logo was somehow representative of Satan worship. In the 1990s, Kentucky Fried Chicken’s publicity department fielded questions about raising eight-legged chickens with no beaks in order to satisfy product demand. In the trifecta of brand disparagement, a rumor circulated in the early 1970s that “Mikey,” the spokes-kid for Life Cereal, had died after mixing Pop Rocks candy with Coca-Cola to produce a combustible blend that blew up his stomach.

In 1993, it was Snapple’s turn. For months, word had circulated in California's Bay Area that the massively popular iced tea and fruit drink brand was secretly funneling money to the Ku Klux Klan organization. The reason? A small “K” appeared on the product label. The rumor persisted to the point that Snapple took out ads in California newspapers to declare they had no involvement with the group.

That such a rumor existed was a kind of testament to the brand's market dominance. Originally founded in Long Island as a regional manufacturer of alternative drinks, Snapple had grown from $13.3 million in revenue in 1988 to $774 million in 1994. Positioned as a healthy alternative to soft drinks, the company used clever marketing, homespun consumer relations, and a relatable spokeswoman to become one of the biggest consumer success stories of the 1990s.

Unfortunately, Snapple’s problems went beyond being falsely affiliated with a racist hate group. Despite their raging success and a $1.7 billion valuation, the company lost sight of the marketing strategy that had catapulted them to a leading position in the beverage market. By 1997, consumers were losing their taste for the “best stuff on earth."

 
 

Arnold Greenberg was running a health food store in 1972 when two old friends joined him in a new venture. Leonard Marsh and Hyman Golden were brothers-in-law and owned a window washing business. On the side, they partnered with Greenberg to create Unadulterated Food Products, Inc., peddling fruit juices, eggs, and produce to other health food stores in and around New York City.

The men intended for their flagship product to be a carbonated fruit juice, combining the fizz of a soft drink with natural ingredients. Their first try, apple juice, fermented in the bottle and exploded, popping off caps and ruining their inventory. The drink was abandoned, but the name—Snapple, a mix of “snappy” and “apple”—stuck. (A company in Texas happened to have already trademarked the name. The three men bought it for $500.)

A bottle of Snapple sits on a table
chrisjtse, Flickr // CC BY-ND 2.0

Unadulterated Food Products did steady business for much of the 1980s selling to bodegas, delis, and other food service locations where people could pick up a bottle to go along with their lunch. In 1987, they had a breakthrough with their approach to iced tea. By bottling it hot, the company was able to avoid adding preservatives, which bolstered their all-natural claims. And by offering it year-round instead of just in the summer, they appealed to consumers who enjoyed the drink in cooler weather.

Snapple embraced their homemade identity. Sipping tea from their wide-mouth bottles was not unlike sipping from a piece of glassware on a porch somewhere; their labels were haphazard in design, the graphics a little lopsided. Compared to the corporate perfection of Coca-Cola, Snapple seemed scrappy.

 
 

Despite the company’s commitment to a casual aesthetic, Greenberg and his partners were taken aback in 1993, when advertising firm Kirshenbaum Bond presented their newest idea for a national ad campaign. They wanted to film the company’s mailroom lady, Wendy Kaufman.

Kaufman had arrived at Snapple in 1991 after getting a referral from a friend’s father who also happened to be a close friend of Greenberg’s. Working in the shipping department, Kaufman took notice of the many letters that were pouring in to the company’s Valley Stream, Long Island headquarters. She asked a supervisor if she could begin responding to them. From there, Kaufman’s job developed into more of a public relations representative.

The ad firm’s idea was to maintain both Snapple’s simplicity and Kaufman’s unrehearsed appeal by shooting a series of television spots that would feature her reading real letters from behind a desk and then following up with the correspondent. One kid wrote in saying he’d make a good mascot; Kaufman showed up with a film crew and took him to mascot school. Another asked Kaufman to be his prom date; she accepted.

For Kaufman, it was an opportunity to distance herself from a self-admitted coke addiction (not the carbonated kind) that had started in 1980. For Snapple, it represented a chance to further their brand identity by passing up the kind of rock star endorsements common in the beverage industry. The 37 commercial spots, shot between 1993 and 1995, were enormously popular, and Kaufman became a mascot on par with Tony the Tiger. She made personal appearances, storming dorm rooms with cases of Snapple. She sifted through 2000 letters a week. Sales jumped from $232 million in 1992 to $774 million in 1994. Snapple was on Seinfeld, on the lips of radio personality Howard Stern, and celebrated for its unique marketing approach.

Then “Crapple” happened.

 
 

In 1992, Greenberg, Marsh, and Golden agreed to sell a majority stake in Snapple to the Thomas H. Lee investment firm, with Marsh remaining on as CEO. Then, in 1994, Snapple was sold to the Quaker Oats Company. As successful as Snapple had been, industry observers were excited to see what a global conglomerate could do to carry the brand further.

As the Harvard Business Review would later point out, fostering an already-successful brand is not as easy as it appears. Quaker Oats had enjoyed an explosion of support for its Gatorade sports drink brand and believed it could apply some of those same strategies to Snapple. Bottles got bigger, from the standard 16 ounces to 32 and even 64-ounce containers. Gone was Kaufman, no longer a good fit for Quaker’s polished promotional plans. They also cut ties with Stern, believing the controversial entertainer didn't reflect Snapple’s growing maturity in the market.

Bottles of Snapple line a store shelf
David Paul Morris, Getty Images

In retrospect, Quaker had erred on all counts. Consumers had little interest in vats of iced tea in 64-ounce containers, preferring to sip smaller bottles at work. They missed Kaufman, who was synonymous with the brand’s irreverence and homegrown feel. And Stern, who could be caustic when he felt minimized by sponsors, began using his considerable airtime to roast Snapple, calling it “Crapple.” The rants were beamed to millions of his listeners at stations around the country.

Quaker had, in effect, misjudged or mistimed Snapple’s graduation from plucky beverage upstart to a dignified institution. The company sold the brand to Triarc for $300 million in 1997. They had paid $1.4 billion for it just three years earlier. Following the sale, Quaker CEO Bill Smithburg resigned from his post.

 
 

Though Snapple’s heyday may have passed, there was still considerable consumer enthusiasm for its more adventurous flavors (like Diet Kiwi Strawberry Cocktail, which was allegedly a favorite among some horses at a Seattle stable) and for a return to less aggressive marketing. In 1997, Triarc invited Kaufman not only to come back and shoot a new commercial but to allow her face to be stamped on every bottle of Wendy’s Tropical Inspiration. And instead of limiting distributors to certain flavors, they shipped out more varied assortments and let consumers decide what they liked.

Triarc’s success was as notable as Quaker’s failure. The company sold Snapple to Cadbury Schweppes in 2000 for $1.45 billion. As part of the Dr Pepper Snapple Group, the brand changed hands once more early in 2018, selling to coffee cup giant Keurig, part of the JAB Holdings investment group, in exchange for $18.7 billion to shareholders.

It’s been a roller coaster of a ride for Snapple, which started in a small health food store, became a part of popular culture, was nearly done in by a misguided marketing plan, and was finally restored to its former glory by a company willing to get back to the basics.

As for that hate group involvement: The “K” on the label never had any connection with Klan activity. It stood for “kosher.”

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