12. Ask.com

Jeeves' butler

Jeeves, the butler mascot for Ask.com, has had a tough decade. The once-competitive search engine's U.S. market share has gone down to 3 percent, according to research firm ComScore.

The butler made his debut in 1996 and was dismissed for a week in 2004, returned slimmer, was fired again in 2006 after InterActiveCorp acquired the company and then returned in 2009 to the U.K. site.

11. Microsoft

Clippy paper clip

Everyone must have felt the irritation this mascot brought in. Clippy, the "helper" cartoon character in Office software was hated for its nagging interruptions. Start a Word document with "Dear," and Clippy would interject: "I see you are writing a letter. Would you like some help?"

Microsoft introduced companion pets, conducted focus groups and hired a Stanford University researcher as a consultant, all to fix Clippy. The company ultimately killed off the character in 2007.

10. Sun

Duke Java blob

Sun Microsystems made Duke, a blobby, triangle-shaped character, the face of Java which at that time was just another software platform.

It was designed by Joe Palrang, who later worked on Shrek for DreamWorks Animation. The Duke character itself was "open sourced" in 2006, legally allowing anyone to tinker with the design.