Balloon year: 1999
Technically a "falloon" -- a float/balloon combination -- Buddy was still about a year away from becoming the sock puppet symbol of the bursting dot-com bubble. It was conspicuous market spending such as this that got Pets.com into trouble in the first place. A Thanksgiving Day balloon, a Super Bowl ad in 2000 and a whole lot of mascot interviews for magazines and talk shows helped the online pet supply retailer blow through $300 million in venture capital in little more than two years.
Balloon year: 2001
Not so much a symbol of failure as the mascot of the Internet's fading old guard, AskJeeves was a novelty with not much else built around it. Founded in 1996, Ask Jeeves was a search engine that searched both by keyword and by answering questions asked of it: Kind of like Apple's (AAPL) Siri with a keyboard and a really bulky monitor. That novel service allowed it to go public under the ticker ASKJ in 1999 and kept it on the market until it was snatched up by Barry Dillers InterActiveCorp (IACI) in 2005. That was the end of Jeeves, as IAC phased out the character and changed the site's identity to Ask.com. By that time, however, nobody really seemed to care. Google (GOOG) had just gone public and IAC was getting busy buying up Internet afterthoughts such as About.com and the parent company of Dictionary.com and Thesaurus.com. Ask.com was reduced to the logo on Bobby Labonte's NASCAR ride. By 2010, Ask.com was out of the search engine game altogether, leaving behind a string of question and answer pages that appear whenever you enter a question into a search engine. Though Jeeves lingered much longer than some of his dot-com counterparts, he serves as a reminder of the fickle nature of the Internet. The state of Ask Jeeves was perhaps best summed up by Aziz Anzari's character Tom Haverford on NBC's Parks and Recreation last season after realizing his own fast-rising business venture was flickering out of existence: "My company is no better than a company where you ask a fake butler to Google things for you."