In other words, it\u2019s been a long time since Ask.com mattered. And yet its demise inspired a flurry of nostalgic reveries<\/a>, focused on its early days, original name, and cartoon butler mascot. That residual fondness reminded me that once upon a time, the company really had something. But instead of capitalizing on what it had created, it gave up\u2014just before it might have been able to fulfill its vision.<\/p>\n Ask Jeeves debuted in 1997, a moment of great expectations for the nascent field of internet search. As the web exploded with content, Ask Jeeves was one of a bevy of startups that emerged to organize it. Yahoo and AltaVista were the big dogs, but others included Excite, Lycos, HotBot, LookSmart, Northern Light, and WebCrawler.<\/p>\n Meanwhile, a couple of Stanford graduate students, Larry Page and Sergey Brin, were working on their own search algorithm. When Google launched in 2008, its results were clearly the best in the business, and its ascent was rapid. In 2001, Ask Jeeves responded by buying a startup called Teoma<\/a>, whose relevance-ranking algorithm was a credible rival to Google\u2019s PageRank. The move certainly felt like a sizable whoop at the time. Or at least it wasn\u2019t yet a given that Google\u2019s momentum was unstoppable.<\/p>\n In 2003, however, Google overtook Yahoo as the dominant search site. After that, there was never a moment when Ask Jeeves, or anyone else, was poised to catch up. Google\u2019s market share steamrolled to 90%-plus, leaving its rivals squabbling over what little remained.<\/p>\n But even after IAC took control of Ask Jeeves\u2014the conglomerate bought it for $2 billion in July 2005 and quickly eliminated the \u201cJeeves\u201d from its name<\/a>\u2014you couldn\u2019t accuse the site of doing too little in search of success. Instead, it was all over the place, flinging new ideas at the wall and barely waiting to see if they stuck before moving on to new ones. In June 2007, it released an all-new design<\/a> that offered tons of useful features Google lacked at the time. By October of the following year, however, it had dumped many of them in favor of an experience<\/a> that felt like warmed-over Google.<\/p>\n As an IAC property, Ask advertised constantly on TV<\/a>, but never landed on a brand promise that stuck. At one point, its commercials positioned the site as being for serious searchers who craved advanced tools. Then they claimed it offered \u201cinstant getification.\u201d Sometimes they didn\u2019t offer any reason to try it beyond the fact that it wasn\u2019t Google.<\/p>\n All along, I rooted for Ask, simply because even hapless competition for Google served consumers better than no competition at all. But it floundered so publicly that it wasn\u2019t surprising when IAC downsized it to a mundane Q&A platform almost 16 years ago.<\/p>\n Okay, back to 2026 and the eulogies<\/a> inspired by Ask.com\u2019s shuttering. As far as I can tell, nobody ever cherished that brand. But boy, did Ask Jeeves and its butler lodge themselves in people\u2019s brains. The vast majority of headlines mentioned both, more than 20 years after they putatively entered retirement. (IAC did bring back Jeeves<\/a> in the U.K. in 2009, in a more dynamic computer-rendered version who bore an eerie resemblance to its chairman, Barry Diller\u2014or at least I thought so at the time.)<\/p>\n In its pre-IAC period, Ask Jeeves bet big on the appeal of its affable, balding mascot, who it maintained was unrelated to writer P. G. Wodehouse\u2019s legendarily capable manservant<\/a>, though it added a credit to its homepage after the Wodehouse estate complained. A company representative told<\/a> Salon<\/i>\u2019s David McDonough that it wanted to make the character as familiar as Popeye. In 1999, Jeeves rode<\/a> on a float in the Macy\u2019s Thanksgiving Day Parade; the following year, he was upgraded to full balloon status.<\/p>\n If you\u2019d compiled a list of the internet\u2019s most familiar fictional characters around the turn of the century, Jeeves would have been on it, along with the dancing baby<\/a>, the Pets.com sock puppet<\/a>, and BonzaiBuddy<\/a>. Apparently IAC preferred a more modern, less whimsical image for its search engine. Still, when it did away with Jeeves, it torched a massive amount of brand equity.<\/p>\n Ask also failed to build on its original potential in a more fundamental way. Ask Jeeves\u2019s very name suggested that it wasn\u2019t about searching the World Wide Web so much as getting answers to questions. Back then, it was a fuzzy distinction, since the answers you sought were generally scattered across the web. But even as IAC was exiting the search business, Google was working on a technology called the knowledge graph<\/a>. When it appeared, in 2012, it dramatically increased the percentage of questions the search engine could answer without routing users to other sites. Ask Jeeves could have offered similar features had it remained in the game.<\/p>\n If the site had held on as a search engine all the way into the generative AI age, it might have become the product it always aspired to be: an engaging, hyper-knowledgeable assistant with an uncanny ability to field questions on any topic. Today, Jeeves could also help us manage our calendars, buy stuff, and take care of personal and professional business far outside the realm of 1990s search engines. He could be the ultimate AI agent\u2014and being personified as a cartoon butler would make perfect sense. (In 2023, Ask Jeeves cofounder Garrett Gruener told<\/a> The Atlantic<\/i>\u2019s Charlie Warzel that he was proud of the product\u2019s prescience and didn\u2019t feel too bad about losing the search wars to Google.)<\/p>\n As I was mulling over what might have been, it dawned on me that even if IAC failed to seize the opportunity to infuse Jeeves with AI, I could. Chatbots are adept at role-playing<\/a>, a fact that is often disturbing<\/a>. But their willingness to take on a persona let me whip up a prompt to turn any bot into a butler.<\/p>\n Voil\u00e0<\/i>:<\/p>\n \u201cUntil I request otherwise, take on the role of Jeeves, an experienced, helpful, extraordinarily competent British butler. Respond to my prompts in a dignified, slightly reserved manner that is deferential but not obsequious. Behave as if you are a salaried employee but also sincerely concerned about looking out for me. Use information you know about my interests and habits to facilitate efficient and thoughtful responses. Decline to undertake any requests that are inappropriate.\u201d<\/p>\n Plugging in these instructions to ChatGPT, Claude, Gemini, and Copilot got me entertaining results\u2014especially in the case of Claude, whose stock personality is crisp and professional in the first place. I don\u2019t plan to use them forever, but resuscitating Jeeves for a few days seems like an appropriate way to mourn one of the 20th-century internet\u2019s true giants. If you’re similarly inclined, give them a try in your favorite chatbot, and let me know what you think.<\/p>\n You\u2019ve been reading<\/em> Plugged In, <\/em>Fast Company\u2019s weekly tech newsletter from me, global technology editor Harry McCracken. If a friend or colleague forwarded this edition to you\u2014or if you’re reading it on fastcompany.com\u2014you can check out previous issues and sign up to get it yourself every Friday morning. I love hearing from you: Ping me at hmccracken@fastcompany.com<\/a> with your feedback and ideas for future newsletters. I\u2019m also on Bluesky<\/a>, Mastodon<\/a>, and Threads<\/a>, and you can <\/em>follow <\/em>Plugged In on Flipboard.<\/em><\/a><\/p>\n A PC trade-in rush is on the way\u2014and it\u2019s coming at the worst possible time![\"\"](\"https:\/\/images.fastcompany.com\/image\/upload\/f_webp,q_auto,c_fit,w_1024\/wp-cms-2\/2026\/05\/IMG_4775.jpeg\")
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