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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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The Time Freddy Krueger Became a Nightmare for Will Smith
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Fans of Will Smith’s music career may think they’ve heard every album and seen every music video from the actor’s days as one half of the hip-hop duo DJ Jazzy Jeff & the Fresh Prince. Thanks to one ill-timed and poorly conceived effort, however, there’s one performance that aired only a handful of times before being permanently pulled. It has never resurfaced on compilations, on MTV, or even on YouTube. And the fault lies solely with Freddy Krueger, who used something even more dangerous than his razor-fingered glove: a small army of lawyers.

A promotional image of Robert Englund as Freddy Krueger
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Back in early 1988, Smith and his musical partner Jazzy Jeff (a.k.a. Jeffrey Allen Townes) released their second album, He’s the DJ, I’m the Rapper. It would eventually go platinum, selling 2.5 million copies through 1989 and spinning off the duo’s most successful single, “Parents Just Don’t Understand.”

In late 1987, Townes composed another single, “Nightmare on My Street,” that played with the premise established by the A Nightmare on Elm Street series. In the song, Smith’s dreams are haunted by a scarred bogeyman named “Fred”; a voice modulator mimics the raspy delivery of actor Robert Englund, who portrayed slasher movie icon Freddy Krueger in the Nightmare on Elm Street films. After his run-in, Smith tries calling Jeff to warn him of the threat but it was too late: The killer has gotten to his partner.

Zomba, the parent company behind the album's label, decided the song might be of interest to New Line Cinema, the studio behind the Nightmare film franchise. With the fourth installment, A Nightmare on Elm Street 4: The Dream Master, due to hit theaters in August 1988, Zomba executive Barry Weiss approached New Line with the possibility of collaborating and forwarded a tape of the song.

Weiss’s timing was spot-on. New Line had recently conducted research that indicated that 40 percent of A Nightmare of Elm Street's audience was black, and they felt that tying Krueger into the burgeoning rap and hip-hop industry would help cement his appeal to the demographic. But New Line and Weiss couldn’t come to a financial agreement. Instead, the studio went with The Fat Boys and granted permission for the song “Are You Ready for Freddy?” The video, complete with an appearance by Englund (in character), was released just a few months prior to A Nightmare on Elm Street 4 to raise awareness of the sequel.

Although New Line found their collaborators, Zomba didn’t appear willing to give up on the idea of a Freddy takeoff. “Nightmare on My Street” remained on the album, and Smith and Townes recorded a video intended for distribution on MTV. In it, Smith is stalked by a Freddy-like character who appears in a trench coat and has a wrinkled face. Smith’s lyrics make overt reference to a Krueger-esque appearance. (Fred is “burnt like a weenie.”) The eerie house Smith calls home even bears a passing resemblance to the house in the original Nightmare film.

If Zomba thought they could declare the song and video a parody and be safe from legal action, they were mistaken. Almost immediately, New Line's legal team sent a stern letter demanding the music label recall all copies of the song. When that didn't happen, the studio next sought a preliminary injunction to prevent “Nightmare on My Street” from being aired on MTV or elsewhere, citing copyright infringement and a concern that the video would detract from their collaboration with The Fat Boys.

"We own both a character, Freddy Krueger, and the theme music from Nightmare on Elm Street, both of which are protected under the copyright laws," Seth Willenson, New Line's senior vice president of telecommunications, told the Los Angeles Times in August 1988. “By using Freddy in the Jazzy Jeff song, they've infringed our copyright. We're protecting our rights the same way that George Lucas does, because as far as we're concerned, Freddy Krueger is the Star Wars of New Line Cinema."

Weeks before the release of the film, a judge in New York’s United States District Court would have to decide whether Zomba was entitled to a fair use exemption over a fictional child murderer.

Will Smith appears at the Grammy Awards
Matt Campbell/Getty Images

To Zomba’s dismay, judge Robert Ward didn’t buy their argument that “Nightmare on My Street” was nothing more than a Weird Al-style satire. Screening the entire first installment of the film series and the music video, Ward noted that the latter drew considerable influence in tone, mood, and characteristics from the feature. Fred’s voice was scratchy like Englund’s; his glove, though it featured phonograph needles instead of razors, was obviously meant to invoke Krueger’s weapon of choice. Where Zomba saw parody, Ward saw little more than a derivative work of a copyrighted property.

“It is in this month that many individuals will make their decision whether Nightmare IV is a film that they are interested in viewing,” wrote Ward in his decision. “Thus, the telecast of the lower quality DJ Jazzy Jeff video with the somewhat silly and less frightening Freddy could dissuade an unspecified number of individuals from seeing the film.” The injunction was granted, with a full hearing to be held at a later date.

That didn’t happen—both parties settled out of court. While the song remained on the record, it began to ship with a disclaimer that it wasn’t associated with New Line; the video, which had aired only briefly on MTV, was pulled, and the court ordered that all copies be destroyed. Whether or not that happened is hard to substantiate, but if the video is lurking in storage somewhere, it has never been excavated. “Nightmare on My Street” has never resurfaced.

If Smith and Townes were bothered by the outcome, they didn’t voice it publicly. Smith even dressed up as Krueger in a 1990 episode of his sitcom, The Fresh Prince of Bel-Air. But there is one additional bit of film trivia to come out of the case: In seeking to resolve the issue, New Line offered DJ Jazzy Jeff and the Fresh Prince a two-film option. If they accepted the roles, their salaries would be deducted from the settlement payout. One of those projects was 1990’s House Party, which the two declined. The roles eventually went to Kid ‘n Play.

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10 Things We Learned From Vanilla Ice's 1991 Autobiography, Ice by Ice
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Vanilla Ice turns 50 on October 31, which will either make you feel very old or compelled to ask a nearby senior who Vanilla Ice is. The hip-hop artist was best known for To the Extreme, his 1990 album that sold 7 million copies, and its breakout single, “Ice, Ice Baby.” He also had a notable turn as himself in 1991’s Teenage Mutant Ninja Turtles II: The Secret of the Ooze before attempting to reinvigorate his career as a Rasta-infused rapper with dreadlocks after his initial novelty wore off.

Before that happened, Ice (a.k.a. Robert Van Winkle) penned Ice by Ice, a 1991 “autobiography” that has no co-author byline but was probably written by a man named Randi Reisfeld, who is thanked by the rapper in the foreword for “putting my thoughts together.” At an economical 164 pages, it’s essential reading for anyone who wanted to know the name of Ice's signature hairstyle (“the beak”) or how women can grab his attention ("dressing super-sexy”). Here are 10 things we learned about the Iceman in this revealing paperback cash grab.

1. HE CUT HIS OWN HAIR.

Even at the height of his fame, Vanilla Ice wouldn’t trust just anyone to get near his trademark pompadour that he dubbed “the beak,” with lines shaved into the sides and a light stripe whooshing through the front. To maintain the look, Ice preferred a DIY approach. “I sit where there’s a mirror behind me and hold another mirror in front of me,” he writes. “That way I can see my whole head.”

Ice was so demanding of his follicles than anything less than perfection would be met with self-banishment. “I don’t like to be photographed unless my hair is perfect—that’s why you’ll see pictures of me in baseball caps a lot.”

2. HE DOESN’T CRY.

“I don’t cry and I don’t know why,” Ice explains. Even when he shattered his ankle as a teenager in a motorcycle accident, Ice didn’t get weepy. The only time he confesses to feeling even a passing sensation of tears is when he was handed plaques for having a platinum record. “My eyes got watery … it’s as close to crying as I’ve ever come.”

3. HE GOT STABBED IN THE BUTT AND LOST FOUR PINTS OF BLOOD.

Vanilla Ice in a Miami Football T
Scott Harrison/Getty Images

As Ice’s popularity grew, much was made of his claims that he grew up in rough parts of Miami and Dallas, where he joined a street gang after his stepfather relocated his family for a job opportunity. Some observers accused him of embellishing his background in order to appear more like a hardcore street urchin. Ice bemoans the fact that he’s felt compelled to pull down his pants to show off the scar on his butt from a knife attack at age 18. According to the rapper, a street fight turned ugly when an attacker pulled a knife and sliced open his thigh and buttocks, requiring an extended hospital stay after he lost four pints of blood. “What they did was put this thing that looked like a Q-tip with alcohol on it down inside my leg to plug up the artery,” he writes. (He didn’t cry, though.)

4. HE WORE MISMATCHED SNEAKERS TO SCHOOL.

Growing up, Ice bounced from school to school, admitting he wasn’t very interested in formal education and jarred by having to be the new kid on a regular basis. To offset that sense of isolation, he began showing up in increasingly outlandish outfits, including wearing mismatched shoes. “I’d wear a boot on one foot and a tennis shoe on the other,” he writes, “wear blue jeans with one leg long, the other leg cut off, stuff like that.”

5. IF HE HAD A PROBLEM, HE REALLY WOULD SOLVE IT.

Ice maintains that he was never comfortable sharing his feelings with others. His mother, who was single until marrying his stepfather when Ice was eight years old, tried to put him into therapy to address his troublemaking ways at school; Ice refused to talk. “I never needed to talk to anyone to solve my problems,” he writes. “A lot of people need someone to talk to, but I’ve never been able to open up and do that. Never could, never will. That’s just the way I am. And that’s just exactly where the ‘Ice, Ice Baby’ hook came from—‘If there was a problem, yo, I’ll solve it.’”

6. HE WOULD SOMETIMES USE DIRTY WORDS.

Jana Birchum/Getty Images

Engaging in rap battles growing up, Ice would occasionally deploy some profanity—not because he necessarily wanted to, but because his competitors had started it and he needed to keep up. “The thing is, I wouldn’t do it unless some other rapper started cursing and dissin’ me and the crowd started liking it,” he writes. "'Cause if the crowd starts liking the cursing part, that means to win you’re going to have to curse back at them.” Ice maintains in the book that his raps were clean on his records because “I don’t need to put in dirty words to express myself.”

7. HE WAS ORIGINALLY KNOWN AS VANILLA M.C.

Ice got his start performing at City Lights, a dance club in Dallas owned by future manager Tommy Quon. With “Robert Van Winkle” not having a ton of appeal on a marquee, Ice decided to take the nickname given to him as a teenager when he was beatboxing and rapping in his neighborhood (“Vanilla M.C.”). But Quon pointed out that there were already a lot of “MCs” in the music business, including M.C. Hammer and Young M.C. “You know, your raps, your rhythms are really smooth, smooth as Ice, in fact,” Quon told him. Writing that “it sounded okay to me,” Vanilla M.C. became Vanilla Ice.

8. HE WAS DRAWN TO WOMEN FOR THEIR LOOKS.

Not one to sanitize his image for the masses, Ice admits that his primary concern when dealing with the opposite sex is whether he finds them attractive or not. “My first impression of a girl, whether I’m going to be drawn to her or not, is based on her looks. I know it’s not fair, but then I see what her personality is like.”

Once Ice establishes a woman could engage him intellectually while still “dressing super-sexy,” he enjoys entertaining them at fine dining establishments. But not too fine. “I like candlelit romantic restaurants, but not those where the menu is so fancy that I don’t know what I’m ordering.”

9. HE GOT AN OFFER TO APPEAR IN A NIGHTMARE ON ELM STREET SEQUEL.

Vanilla Ice and Kristin Minter star in 'Cool as Ice' (1991).
Universal Home Video

Ice’s career could have gone in multiple directions following the success of To the Extreme. He filmed a cameo in a Teenage Mutant Ninja Turtles sequel and had his own starring vehicle in 1991’s Cool as Ice. In between those projects, Ice was offered a small role in a Nightmare on Elm Street sequel, presumably to be murdered by Freddy Krueger, “but I didn’t have room in my schedule to take time off for it.” 

10. HE WAS STALKED BY A SATANIST.

We’re cheating slightly, since Ice doesn’t disclose this fact in his book, but it’s still worth noting. At height of Ice mania in the 1990s, the rapper told Rolling Stone that a woman began following him around in an attempt to convert him to Satanism. Ice first noticed the woman at Wembley Stadium when she flashed him in a trench coat. (See: number 8.) Later, the same woman followed him to Japan and left a book under his hotel door: a Satanic Bible, with a personal message to join the flock. Why? Because his birthday falls on Halloween.

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