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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.

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Photo Illustration by Lucy Quintanilla, Mental Floss. All images, iStock
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The Pom-Pom Hit: When Texas Was Struck By a Cheerleader Mom's Murder Plot
Photo Illustration by Lucy Quintanilla, Mental Floss. All images, iStock
Photo Illustration by Lucy Quintanilla, Mental Floss. All images, iStock

On a January morning in 1991, Wanda Holloway was faced with a decision: Realizing that she couldn't afford two murders, the 36-year-old married mother of two had to decide whether to order the killing of her rival, Verna Heath, or Verna’s 13-year-old daughter, Amber.

It was a toss-up as to who presented the bigger problem to Holloway. Amber was an eighth-grader who had the talent and poise to consistently knock out Holloway’s daughter, Shanna, from a spot on their school’s cheerleading squad in Channelview, Texas; yet Verna was the one who pushed Amber, getting her into gymnastics and even being so bold as to let Amber try out for the junior high cheerleading squad before she had even formally enrolled in school.

Killing Amber would guarantee Shanna a berth to cheerleading stardom. But there was a problem: Holloway's ex-brother-in-law, Terry Harper—whom she enlisted to help her carry out her plan—said the man he knew who would accept the assignment wanted $5000 to kill a minor. Bumping off Verna would be a comparatively reasonable $2500.

In a perfect world, $7500 would get rid of them both, but Holloway simply didn’t have the money. So she decided it would be Verna. In addition to being cheaper, she figured Amber would be so devastated by her mother’s death that she couldn’t possibly get through cheerleader tryouts that March.

On January 28th, after dropping Shanna off at church, Wanda met with Harper to give him her diamond earrings as a down payment. Within a matter of days, she would make national headlines as the mother who would do anything for her daughter. Even if it meant life in prison.

 
 

A suburb of Houston, Holloway's hometown of Channelview, Texas sits in a state where football fields are considered holy ground and small town players are revered for their athletic prowess. Boys were expected to suit up if they wanted social status; girls could obtain a measure of popularity along the sidelines as cheerleaders. In both cases, the fitness and discipline required could help provide a foundation for a transition out of adolescence.

As a young woman, Wanda Holloway wanted to join that clique. Her father, a conservative Baptist, vetoed the idea. The costumes were too revealing, he said, too sexualized. Reporters would later seize on this detail and use it to craft a kind of super-villain origin story for Holloway—a woman who was determined to see her own daughter succeed where she hadn’t.

Holloway remained in Channelview and, in 1972, married railroad warehouse employee Tony Harper. They had two children: Shane in 1973 and Shanna in 1977. She divorced Harper in 1980, remarrying twice and retaining custody of the kids.

As Shanna grew older and grade school activities increased, Holloway was determined that her daughter would enjoy some of the opportunities her own father had denied her. She urged Shanna to try out for the seventh-grade cheerleading squad; though Shanna didn’t feel as passionately about the team as her mother did, she tried her best but didn’t make the cut as three girls were vying for two open slots. It was apparently vexing to Holloway that one of the girls who made the team didn’t even attend Alice Johnson Junior High during tryouts: She was still transitioning from a private school. That student was Amber Heath.

Amber and Shanna had purportedly been friends, even having sleepovers at each other’s homes. But Holloway perceived both Amber and her ambitious mother, Verna, as obstacles to Shanna’s progress in cheerleading. Verna had printed flyers and handed out candy during that seventh-grade coup. The next year, Holloway decided to make an offensive move and passed out rulers and pencils that urged Shanna’s classmates to vote her into the squad: “Vote for Shanna Harper for Cheerleader.”

The vice principal intervened, saying such campaigning was against school rules. (Verna's flyers had somehow skirted any penalty.) When Holloway ignored him, parents of other cheerleader candidates—Verna included—held a meeting and voted to disqualify Shanna from being in the running. Shanna was now 0-2, and Verna had made it personal.

As tryouts loomed for ninth grade in 1991, Holloway decided she couldn’t take any more chances with the Heaths. She approached Terry Harper, her first husband’s brother, the one man she knew with some slightly delinquent criminal tendencies. Harper had been arrested a few times on misdemeanor charges. To the best of anyone’s knowledge, he didn’t travel in the kinds of circles where he might know any hitmen. But Holloway seemed convinced that Harper had the connections to make Verna and Amber go away.

Harper would later tell police that he brushed off Holloway’s solicitations but she was persistent. Realizing she was serious, he went to the sheriff’s department, where officers expressed the same initial skepticism. Murder-for-hires didn’t happen in Channelview. When Harper insisted, they wired him with a microphone so he could continue his dialogue with Holloway.

In six separate recorded conversations, Harper found Holloway hard to pin down when it came to an explicit admission of her desire to have Verna murdered.

“You want her dead?” Harper asked.

“I don’t care what you do with her,” Holloway replied. “You can keep her in Cuba for 15 years. I want her gone.”

Semantics aside, Holloway’s intent was clear. Days after she handed over her down payment to Harper for the (fictional) assassin, police arrested Holloway for solicitation of capital murder. Investigators would later remark that Holloway seemed unfazed by the charge.

Out on bail, she told Shanna what she was facing: a potential verdict of life in prison. Although Shanna knew her mother wanted desperately to see her on the team—much more than Shanna herself cared to—she had no idea the rivalry with Verna had escalated to potential homicide. And despite the wishes of her biological father, Shanna remained at Alice Johnson High, avoiding eye contact with Amber Heath practically every day.

 
 

Holloway was arraigned in February 1991, and pled not guilty. Her defense was that the plot had been cooked up by her ex-husband, Tony Harper, and his brother in order for Tony to secure custody of their kids. Her desire to see Verna “gone,” she argued, was simply a joke.

The jury wasn’t laughing. In September 1991, it took them just two and a half hours to find Holloway guilty and sentence her to 15 years in prison—“poetic justice,” as one juror later put it, for wishing Verna would be exiled to Cuba for the same length of time.

Poetic or not, Holloway didn’t do 15 years—or even 15 months. She was granted a new trial in November of that year and the verdict was overturned on appeal in 1996 after it was discovered one of the jurors had been on probation for a drug possession charge and shouldn’t have been serving. Rather than fund another trial, Harris County prosecutors allowed Holloway a plea bargain where she received 10 years but ultimately served only six months in a work camp pulling weeds before being released on probation.

The last time a journalist caught up with Shanna was in 2012, when the then-34-year-old teacher discussed raising her own two children and having an infamous mother with a reporter from People. Living in Humble, Texas, she said she still saw Wanda on a regular basis, although the two rarely discussed the murder plot. Shanna asked about it back in 2010. Holloway called the entire incident a “mistake” and said that she was “sorry.”

When Wanda's future as a free woman was still up in the air, Alice Johnson High went ahead with cheerleader tryouts on March 22, 1991. Amber appeared and made the cut. Shanna did not. She was too distraught to show up.

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GunsNRosesVEVO via YouTube
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When 'November Rain' Excited, Confused Rock Fans
GunsNRosesVEVO via YouTube
GunsNRosesVEVO via YouTube

Slash had no idea what it was about. Axl Rose insisted it be based on a short story. At roughly nine minutes, it stretched the patience of MTV’s viewers. For these reasons—or maybe in spite of them—the music video for the Guns N’ Roses hit “November Rain” remains one of the most infamous, impenetrable rock operas of all time.

“November Rain” was a single from the group’s Use Your Illusion I album. Released in 1991, it broke into the Billboard top 10 and immediately entered music trivia lore as the longest song to make that list. Rose had started writing it in 1983, with an original running time of more than 20 minutes.

For the video, which was released in February of 1992, the group hired director Andy Morahan, who had supervised two previous G N' R efforts: Don’t Cry and You Could Be Mine. Rose also enlisted friend and writer Del James to allow them to loosely adapt one of his short stories, “Without You,” about a singer haunted by the death of his girlfriend. Model Stephanie Seymour, Rose’s girlfriend at the time, played the bride.

The crew respected the band’s wishes for an increasingly epic approach to their videos by going on location to shoot a wedding ceremony between Rose and Seymour at a makeshift church in a New Mexico desert—fabricating it cost $150,000—and arranging for a concert shoot with 1500 extras; Slash’s guitar solo was covered with swooping helicopter shots.

Speaking with authors Rob Tannenbaum and Craig Marks, Morahan described the indulgent nature of the era: “You’ve got five cameras, cranes, helicopter, this big crew.” He recalled one observer asking him, “Is this the whole video? ‘No, it’s about 27 seconds of it.’” (The video cost a then-record $1.5 million.)

Though Seymour’s character appears to be elated at the reception, the video implies she commits suicide shortly after.  


The couple in happier times.

GunsNRoses VEVO via YouTube

Or not. No one really seems to know what happened. “To tell you the truth, I have no idea," Slash told The Huffington Post in 2014. It was a concept. The song itself is pretty self-explanatory, but the video is so complex ... I knew there was a wedding in there somewhere and I was not into the concept of the wedding." Morahan said he has "no idea" why Seymour was shot in a casket with half her face obscured by a mirror.

While the spot wasn’t heaped with MTV Video Music Awards praise (though it did win one, for Best Cinematography, and earn a nomination for Best Art Direction), it has aged well. By the end of 1992, viewers had voted it their favorite video of the year. Morahan, James, and Rose were even asked to collaborate on an episode of HBO’s Tales From the Crypt.

That didn’t come to pass. But even today, November Rain stands as one of the most-played music videos of the 20th century on YouTube, with more than 940 million views. Watch it enough, and maybe it’ll begin to make sense.

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