Most underwhelming product launch
Windows 1.0's release registered as barely a blip on the computing world's radar. Begun in 1981 and initially dubbed "Interface Manager," Microsoft's first graphical operating system was announced in 1983 but not released until 1985. It didn't run as a stand-alone operating system; instead, users had to launch it from within DOS. And by the time it was released, its thunder was stolen by Apple's Macintosh computer and graphical Mac operating system, which launched in 1984.
Most game-changing product launch
In May 1990, Microsoft brought graphical computing to the masses with the launch of Windows 3.0. Versions 1 and 2 of Windows were underwhelming, underpowered and largely ignored, except by people who needed a runtime version to operate software that required windows, such as PageMaker. But the third time was the charm.
Although windows-based operating systems were in use elsewhere, notably on the Mac, Windows 3.0 was a revelation for PC users, with a graphical interface, multitasking and copy-and-paste, among other features. Finally, a reason to buy a mouse!
Splashiest product launch
In 1995, Microsoft launched Windows 95, with an advertising campaign that was estimated to have cost $300 million and was said at the time to be the biggest in history. Microsoft is rumored to have paid $12 million just to buy the rights to the Rolling Stones' "Start Me Up," which was Windows 95's theme song and inescapable anthem.
In addition to a massive television-radio-and-PR blitz, Microsoft draped a 300-foot Windows 95 banner over Toronto's CN Tower, paid for a print run of 1.5 million copies of The Times in London and distributed them for free, and had New York's Empire State Building lit up with Microsoft's corporate colors of yellow, red and green.
As David Segal wrote in The Washington Post on August 24, 1995, "You can hide under a bridge, row a boat to the middle of the ocean or wedge yourself under the sofa, cover your ears and then hum loudly. But get near a newspaper, radio, television or computer retailer today and you will experience the multimillion-dollar hype surrounding the launch of Windows 95."
Best and worst browser launch
In September 1997, Internet Explorer 4 launched, cementing Microsoft's browser dominance and ultimately killing Netscape Navigator as a competitor. With the introduction of IE4, Microsoft also tied Internet Explorer more deeply to Windows. This came back to haunt the company when it was sued by both the U.S. government and the European Union for anticompetitive behavior, including using Windows to force people to use Internet Explorer instead of competing browsers.
Worst interface
Go to any list of the worst software ever written, and 1995's Microsoft Bob will be on it. Designed for Windows 3.1 and later Windows 95, it was supposed to be a user-friendly interface to help nontechies use computers. Instead, it was so cloyingly cute that, in comparison, photos of big-eyed puppies appear to be deep and meaningful. (As Harry McCracken wrote in a PC World review, "It seems to be aimed at a six-year-old who has personal finances to manage.")
Bob was also confusing to navigate; sucked up system resources, reducing computers to a crawl; and was widely derided in the general and tech press. Users stayed away in droves.
Microsoft Bob was overseen for a time by Melinda French, who was Bill Gates' girlfriend at the time and later became his wife.
If you want to see Bob in action yourself, check out this video of Bob. (Warning: The video contains extreme stupidity, horrendous interface design and a nonstop stream of intense monotony.)