#6 Gates' TV Spot

During the dark days, when Microsoft came under scanner, U.S. Department of justice was underway into antitrust investigation against the company; Microsoft’s corporate marketing organization came up with an idea, which insulted brilliance. The team thought that it would be helpful to put company’s founder and chairman, Bill Gates, on the air to speak directly with American people. 

This idea manifested into a TV commercial, where Gates in Blue Sweater, seated at a table, with acoustic guitar playing in the background. This Ad was meant to soften the prevailing image of Microsoft as a monopolistic bully, and Gates says at one point “we've been writing great software for the past 25 years." It did not change anything and escaped people’s notice completely. But a few years later, internet meme envisioned Gates as a Borg, declaring, “Resistance is futile.”

#5 Tablet PC

Microsoft released Windows XP Tablet PC edition in 2002, eyeing to gain from first players in slate market. The device was immature. The shaky handwriting recognition, limited functionality, and expensive components scurried away the users. "I strongly urge any potential customers to seriously consider how, when, and if they would ever actually use the tablet-based features of this product," said Windows Guru Paul Thurrott at the time of launch.

Again lesson half learned, after the flop show of Windows XP Tablet, Microsoft came up with Origami, which was the Ultra-Mobile PC. The InformationWeek editor at the time declared it “the hands-down winner for Most Disappointing Product Of 2006."