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Why Everyone Stopped Asking Jeeves

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In 14 novels by comic author P.G. Wodehouse, spread over the course of a half-century, a fictional valet named Reginald Jeeves fielded questions of sartorial, societal, and personal etiquette posed by his employer, wealthy London socialite Bertie Wooster.

By the late 1990s, he was being asked where internet users could find nude photos of actresses.

It should be noted that the Jeeves of the Wodehouse books, which were eventually used as a template for the BBC series Jeeves and Wooster, was not quite the same Jeeves of AskJeeves.com, the web portal that debuted in 1997 and encouraged search engine users to field their curiosity in the form of a question. (“What’s the best restaurant in San Diego?” “What is Pamela Anderson’s home address?”) But enough similarities remained for the Wodehouse estate to toy with the idea of litigation in 2000, asserting the dot-com had co-opted the character without any financial arrangement.

That would prove to be the least of the site’s problems. After a spectacular initial public offering (IPO) on the stock market that rocketed from $14 to $190.50 a share, Ask Jeeves became a casualty of the search engine wars of the early 2000s. Eventually, their mascot would be escorted right out the door.


The original AskJeeves.com launch page.
Internet Archive

Long before Apple’s Siri and Amazon’s Alexa, Garrett Gruener had a notion to humanize information-gathering online. A graduate of UC San Diego, Gruener had been a venture capitalist in the burgeoning computing world of the 1980s. After founding and selling off Virtual Microsystems in the 1980s, he looked for other ways to explore the market and the potential of the internet to become a consumer-friendly user space.

By 1992, Gruener had an interface, but no face to put to it. He liked the idea of a virtual concierge, similar to the hotel employee who fields guest requests, but didn’t think Americans would know exactly what the word meant. He went with a butler motif instead, and named him Jeeves—not after the Wodehouse character, he claimed, but more in line with how the name had become synonymous with servitude. In partnership with his former Virtual Microsystems employee David Warthen, Gruener launched Ask Jeeves in April 1997.

Although Yahoo!, Alta Vista, and Excite were all in the market, Gruener felt Ask Jeeves set itself apart with its interface. His team had spent months building a library of "knowledge capsules," snapshots of answers to questions they felt would be most commonplace. If a question wasn’t addressed in their content, the site would default to a more general search.

For users overwhelmed with pages of results stemming from a simple search, Ask Jeeves was more refined—dignified, even—with Jeeves standing at attention near the search bar. Many of the queries were consumer-oriented—asking for the best eateries, plumbers, or hotels—while others sought the kind of information that required both urgency and specialized knowledge. “How to get rid of skunk smell?” was one common query. (Salaciousness won the day, however. One in five questions pertained to finding nude photos.)

Gruener’s hunch was correct. People enjoyed the direct, personalized navigation, and saw themselves as Ask Jeeves loyalists. He once compared them to Mac users, who had tunnel vision when it came to alternatives. By 1998, the site was handling 300,000 searches a day. By 1999, it was up to 1 million. After going public, shares climbed from $14 to $60 to $190.50.

Jeeves was poised to be the internet’s first breakout character. He appeared in a Macy’s Thanksgiving Day Parade float, reportedly the first web-based personality ever to do so. The site signed with high-profile Hollywood agent Michael Ovitz and plotted an aggressive merchandising campaign that would see toys, apparel, and other product further familiarize Jeeves to the public.

(None of this was lost on the Wodehouse estate, which questioned whether Ask Jeeves had infringed on their rights to the Jeeves character. While they owned the butler, the Jeeves of the web was not quite the Jeeves of the books, and both parties announced a non-disclosed settlement in 2000.)

Jeeves would finally lose his composure in 2001, when the dot-com bubble burst. Advertisers fleeing from web development led to mass casualties online. The company posted a $425 million loss in 2001; shares plummeted to 86 cents in 2002. Despite his sharp appearance, Jeeves was dangerously close to insolvency.


search-engine-land via Flickr // CC BY 2.0

Ask Jeeves would rebound from those dark times. The site was reconfigured to be more search-oriented with the addition of a third-party engine, and Jeeves was recast as more of a mascot; a 2003 ad campaign didn’t even feature him. That same year, Gruener was able to post the company’s first-ever profit, thanks in large part to an ad revenue deal with Google. But the behemoth in the search engine space wasn't sharing the market: It owned 32 percent of the industry compared to just 3 percent for Ask Jeeves.

In 2005, Barry Diller’s InterActive Corp. (IAC) purchased the site for $1.85 billion with an eye toward making it less about questions and more about general searches. Gruener departed; Ask Jeeves morphed into Ask.com, with the butler disappearing entirely the following year.

Why? Perceiving Jeeves to be representative of the 1990s internet culture, Diller and IAC believed his charm had run its course. “I don't see many tears on the floor," Diller said about the character’s absence.

While Diller had designs on being competitive with Google, it was not to be: That site went on to claim a clear dominance of the search market. By 2010, corporate support for Ask.com had dwindled, although the URL remains a part of the search engine landscape. Aside from a brief return in 2009 in the UK, Jeeves has been unavailable to field any additional questions.

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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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