Best follow-up OS
Again we've got a toss-up here, between DOS 5, which fixed DOS 4's many problems, and Windows 7, which cured Vista's. I'll choose Windows 7, which is the OS that many people believe Windows Vista should have been. It is faster than Vista, does not have the same hardware incompatibilities, dumps some useless applications, and delivers some nice tweaks, including an innovative, much-improved taskbar.
The proof is in the pudding: Both businesses and consumers are finally beginning to let go of nine-year-old XP and make the jump to Windows 7.
In July 1993, Microsoft launched Windows NT. Designed for businesses rather than consumers, NT was constructed from the ground up, not built on top of DOS as previous versions of Windows had been. More stable and more secure than Windows 3.1, NT was the first completely 32-bit version of Windows. Its first release was called NT 3.1 to match the consumer version of Windows, but it was put on its own development cycle with its own naming conventions, culminating in Windows 2000, which was released in 2000.
Ultimately, the business and consumer lines of Windows were merged in Windows XP, released in 2001, and the NT kernel became the core of XP and all subsequent versions of Windows -- which means that except for a scattered few diehards still using the Windows 3.x and 9x lines, all of today's Windows users are using a direct descendant of NT.
Biggest under-the-radar success
A lesser-known product success story is Microsoft SQL Server, which has a somewhat checkered history. It began in 1988 as a joint venture among Microsoft, Sybase and the now defunct Ashton-Tate, and was designed for the troubled OS/2 operating system.
The product was largely a port of Sybase SQL Server 3.0, which ran on a variety of operating systems, including Unix and VMS. Microsoft and Sybase ultimately parted ways, with Microsoft developing SQL Server for Windows NT and Sybase changing the name of its version to Adaptive Server Enterprise.
These days, SQL Server has grown to become the third most popular database software in the world, behind those of Oracle and IBM.
Smartest software bundling
Clearly the smartest software bundling move Microsoft ever made was combining Word, Excel and PowerPoint into Microsoft Office, first for the Mac in 1989 and then for Windows in 1990.
Microsoft Word, which Microsoft originally (internally) called Multi-Tool Word, was released in 1983 for MS-DOS, in 1985 for the Mac and in 1989 for Windows. Excel was launched in 1985 for the Mac and in 1987 for Windows. Also in 1987, Microsoft released PowerPoint for the Mac, essentially a version of an application called Presenter that was created by Forethought, a company Microsoft had purchased that year. In 1990, PowerPoint for Windows was released.
Excel fun fact
When Excel was first developed, Microsoft already had a spreadsheet called MultiPlan, but it was not selling well on the MS-DOS platform. The company decided it needed a much better offering to compete against Lotus 1-2-3, the best-selling spreadsheet program at the time.
Thus, Excel was originally code-named "Odyssey" because it was intended to eat Lotus. (In Homer's The Odyssey, Odysseus' crew members ate the narcotic lotus plant in the Land of the Lotus.)
Microsoft's bundling of Word, Excel and PowerPoint into the Office suite emphasized the company's commitment to business desktop computing. It proved to be a huge success, ultimately leading to the downfall of onetime market-leading applications Lotus 1-2-3 (spreadsheet), WordPerfect (word processor) and Harvard Graphics (presentation program) -- and to a near-monopoly for Microsoft Office in the business world.
Sneakiest software bundling
I'll give the award for sneakiest software bundling, hands-down, to Windows Genuine Advantage (WGA), Microsoft's antipiracy software. WGA warns people when they do not have a paid-for and registered version of Windows, and certain updates can't be installed unless WGA is installed and has verified that the copy of Windows is genuine.
In mid-2006, Microsoft began sending WGA to users' computers along with security updates via Windows Update; the company even labeled the WGA download as "high-priority." Unbeknownst to users, though, the update had nothing to do with security or stability -- it was WGA, sneaking onto their hard disks.
As Computerworld's own Scot Finnie wrote in July of 2006, "Microsoft is preying upon people's ignorance -- and their strong desire to install security updates. It's clearly wrong for Microsoft to use its security updating channel to install software that has no security benefit, and no benefit at all to its customers."
Users were frustrated enough that a lawsuit was filed, although the suit was recently dismissed in federal court.