In November 1999, stickers on grocery store bananas asked how many calories were in the fruit and pointed shoppers to a web address. That was Ask Jeeves, founded in Berkeley, California, in 1996 on a simple bet: people should be able to type a question in plain English instead of learning keyword and Boolean syntax. A cartoon valet borrowed from P.G. Wodehouse made the idea obvious to novices, and by July 1999 the company was trading on the NASDAQ.

This episode follows three decades of reinvention, from the Teoma acquisition and a $1.85 billion sale to IAC in 2005, through the 2006 decision to retire the butler and become Ask.com. It covers the privacy tool AskEraser, the purchase of Dictionary.com, a NASCAR sponsorship, and the 2010 surrender in the search wars. What kept the site alive for another 16 years was a quieter business built on old query logs, ad-heavy answer pages, and Google’s own rankings, until the servers went dark on May 1, 2026.

• The original system was not thinking at all. It stripped a question down to its core terms and intent, then matched it to answers and links organized by human editors.
• A giant Jeeves balloon floated in the Macy’s Thanksgiving Day Parade every year from 2000 to 2004.
• Teoma, developed by researchers at Rutgers University, ranked pages by links from sites on the same subject instead of by raw popularity.
• AskEraser launched in December 2007, letting users opt out of having their queries, IP addresses, and cookies recorded.
• In 2010 Ask.com shut down its web crawler and laid off 130 search engineers, then bought About.com in 2012 and Ask.fm in 2014 to turn curiosity into ad revenue.