Microsoft turns 35: Best, worst and most notable moments

An opinionated look back at the good, the bad and the ugly of Microsoft's 35-year history

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Most prophetic memo

In February 1976, Gates issued a public letter berating people who were freely distributing tapes of the version of BASIC he and Paul Allen wrote for the Altair, without paying Microsoft for them. Here are excerpts from Gates' "An Open Letter to Hobbyists," sent to the Homebrew Computer Club:

The amount of royalties we have received from sales to hobbyists makes the time spent of Altair BASIC worth less than $2 an hour.

As the majority of hobbyists must be aware, most of you steal your software.... Who cares if the people who work on it get paid?

Who can afford to do professional work for nothing? What hobbyist can put 3 man years into programming, finding all bugs, documenting his product and distribute for free?

Although the term open source hadn't been coined at the time, this letter set the stage for Gates' career-long battle with open-source and free software advocates.

Most beloved OS

Two operating systems stand out in Microsoft's long history as having more than their share of fans: MS-DOS 5 and Windows XP. Released in 1991, MS-DOS 5 was stable, fixed the worst problems of its notoriously buggy predecessor, MS-DOS 4, and for the first time broke the 640K memory barrier for DOS, allowing memory beyond that to be used for programs, drivers and so-called Terminate and Stay Resident (TSR) programs.

With 2001's Windows XP, Microsoft finally merged its consumer and business lines of Windows, essentially building a consumer-oriented operating system on top of the stable Windows NT kernel. It also finally stopped using DOS as the base operating system, making Windows XP far more stable and reliable than previous versions of Windows.

Save XP
InfoWorld launched a campaign to save Windows XP in 2008.

Some people believe XP was too much of a success, because Microsoft has had a hard time getting people to give it up for newer Windows versions. In 2008, more than 200,000 users signed InfoWorld's "Save XP" petition asking Microsoft to continue support for the aging operating system.

Which is the most beloved? I'll give the nod to Windows XP. MS-DOS 5, as good as it was, ultimately led to a dead end -- it was the best operating system in a line that eventually died out. Windows XP, in contrast, lives on not only on many people's computers, but in the heart of Windows 7, which still retains its predecessor's merged business and consumer lines.

Most reviled OS

Here you've got to choose among an unholy trifecta of MS-DOS 4, Windows Me and Windows Vista. Released in 1988, MS-DOS 4 was notoriously buggy, and many applications refused to run on it. Users commonly reverted to MS-DOS 3.3 or jumped ship to Digital Research's DR-DOS 3.41 to avoid MS-DOS 4, Microsoft's first serious misstep in operating systems. Windows Me, released in 2000, was buggy as well, and plagued by installation problems and a plethora of hardware and software incompatibilities.

The Windows Vista desktop
The Windows Vista desktop.

But I give the "most reviled" crown to 2006's Windows Vista, which proved to be far more of a fiasco than Windows Me or MS-DOS 4. The five-year gap between the release of XP and Vista was the longest gap between versions of Windows ever, so people had high expectations for Vista. Unfortunately, it was bedeviled by hardware incompatibilities at launch, it wouldn't run on older hardware, and many people disliked its resource-hungry user interface.

Making matters worse, many PCs that were tagged as "Vista Capable" couldn't run the full version of the operating system -- a situation that led to a class-action lawsuit against Microsoft.

(Related reading: Opinion: The top 10 operating system stinkers)

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.

Furthest-reaching OS

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.

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