Buddy from Pets.com
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.
By the following Thanksgiving -- less than 300 days after its stock went public -- the company had liquidated all its assets. The rights to the Michael Ian Black-voiced puppet Buddy were sold to an auto loan company, who used the sock-puppet in commercials featuring the message "Everyone deserves a second chance." Surprisingly, the dot-com bubble would get that second chance with yet another Thanksgiving balloon ...
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.
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