Microsoft Windows: 30 Years of Hits and Misses

The Microsoft Windows XP log-in screen is displayed on a lap
The Microsoft Windows XP log-in screen is displayed on a laptop computer in Essex, U.K., on Monday, April 27, 2009.
Photograph by Bloomberg via Getty Images

For many who live in a MacBook Pro-iPhone bubble, it’s easy to forget just what a phenomenon Microsoft Windows has been for three decades now. It is, after all, run by more than a billion people. As Charles Fitzgerald, a former Microsoft exec, put it: “Windows made technology a mainstream consumer phenomenon.”

On November 20, the venerable operating system had its 30th birthday and as someone who’s covered Microsoft on and off for much of that time, here’s a highly selective pick of hits and misses (with an assist from friends.)

First, the high points:

1.The Windows/Office killer tandem

In the late 1980s, Microsoft launched Office, a bundle of its Word word processor, Excel spreadsheet, and PowerPoint graphics for Windows. The combined package, which really was not at all integrated at first, cost less than what each individual application would have cost separately at retail. That felt like a good deal, even though most buyers never would use all three applications.

It was brilliant marketing and also the beginning of the end for the incumbent powers in the word processing, spreadsheet, and graphics categories which were WordPerfect, Lotus 1-2-3 and Harvard Graphics respectively. It was also the start of Microsoft’s (MSFT) staggering dominance in desktop applications. WordPerfect, Lotus, and Software Publishing—the company behind Harvard Graphics— all bet on OS/2, the operating system backed by IBM(IBM) and Microsoft, initially.

In 1991, Microsoft and IBM divorced over the OS/2 issue and Microsoft proceeded with a Windows-first development policy, much to the chagrin of IBM and allied application developers, many of whom now viewed Microsoft as much a competitor as a partner. How many people do you know who run OS/2 now?

2. Windows 95

It’s hard to overstate how big a deal this product launch was. If Windows 3 was a good version of the PC operating system, Windows 95 was the killer version. In this release, the company incorporated MSN, an online service that took on America Online, Compuserve, MCI and Prodigy, the three dominant online communities of the time. Each hosted its own, incompatible email system.

Brad Silverberg, the Microsoft exec who drove Windows 95, remembers the “blow-out” company party in July to celebrate release to manufacturing (or RTM) when the “golden disc” was shipped to production. In these pre-download days, software companies had to build the discs for distribution to hardware makers and retailers.

Then in August, there was the official and very public launch party, on the Redmond, Wash. campus, complete with a Ferris wheel and Jay Leno sharing the stage with Bill Gates. Just huge. Oh, and entire campaign kicked off with a TV ad featuring the Rolling Stones Start Me Up Classic.

People lined around the world at stores to get their copies. The logo was splashed on the Empire State Building and the CN Tower, Silverberg, recalled via email. Many of those involved attended a 20th anniversary bash at Microsoft in July.

3. Apple and Microsoft make nice

Few industry events were as dramatic as Bill Gates’ surprise appearance at Macworld 1997 in Boston, not long after Steve Jobs re-joined Apple(AAPL) from his exile. At that time, the two companies were partners but also very much at odds over patents and other issues.

So when Jobs announced that Apple would make Microsoft Internet Explorer the default browser on the Mac, there were boos and hisses. When he said Microsoft would invest $150 million in Apple, there was consternation that lifted only when he added these were non-voting shares. And when a gigantic image of Bill Gates was beamed in via satellite, dwarfing Jobs, the hissing and booing drowned out applause.


But this pact helped Apple get back on its feet, and softened Gates’ image as a soul-less opportunist. (Believe me, much worse things were said about him at the time.)

4. The rise of Satya and a less dogmatic Microsoft

Given Microsoft’s Windows-first history, it was a shocker last year when the company, under new chief executive Satya Nadella quietly stripped the “Windows” off of its Windows Azure branding.

This was significant, as is Microsoft determination to make its Azure cloud a home for non-Windows technologies including a roster of open-source offerings. To think that Azure runs Linux workloads is quite a turn about from the days when former chief executive Steve Ballmer likened Linux to cancer.

This shows a mature realization that millions of developers cut their teeth on open-source technologies, not proprietary tools like Microsoft’s own Visual Basic.

5. A keen eye for talent

Microsoft leadership through the decades had a keen eye for tech talent and was able to recruit a lot of it. Case in point: Dave Cutler, formerly of Digital Equipment, who was brought on to build the next-generation operating system, which went on to become Windows NT, according to former Microsoft senior vice president Bob Muglia, now chief executive of Snowflake Computing, a data warehousing startup.

And Brad Silverberg, who gave Microsoft fits when he worked at rival Borland International, but who then came over to run Windows and then Internet Explorer. Or Ray Ozzie, the technologist behind Lotus Notes, one of the first collaboration applications.

All were with competitors and ended up with top jobs at Microsoft. In fact, Ozzie, once described by Gates as one of the best programmers in the universe, replaced Gates as chief software architect in 2006.

Snippet from Ray Ozzie's notes from a WIndows planning meeting in 1985.
Snippet from Ray Ozzie’s notes from a WIndows planning meeting in 1985.Ray Ozzie
Ray Ozzie

But, yes, there were lows. Lots of them.

1.Microsoft the Monopolist

Many have forgotten, but in early 2000, Microsoft was ruled to be a monopoly that unlawfully parlayed its strength in one area to gain dominance in others.

As Federal Judge Thomas Penfield Jackson wrote in his judgement:

“The court concludes that Microsoft maintained its monopoly power by anticompetitive means and attempted to monopolize the Web browser market.”

The verdict, which endorsed the U.S. Justice Department’s recommendation that Microsoft be broken up into two companies, was thrown out on appeal because Jackson had given interviews during the appeal process that seemed to indicate bias.

Even though Microsoft avoided the axe—on a technicality—the long-running investigation and trial was a huge distraction and really damaged its reputation. Gates, whose testimony was likened to that of a petulant child, certainly didn’t help.

This was, Muglia said, was “without a doubt, the most prolonged, painful, and destructive event in Windows history.”

And its impact on Microsoft and the industry was huge, in his view. “At the time it was believed that Windows was so entrenched that Microsoft would forever hold an impenetrable position and would always dominate the industry. So much for that,” he noted via email.

2. Whoops, we missed the Internet

The flip side of all the Windows 95 success was that the focus on beating AOL, Compuserve, MCI, and Prodigy meant the company failed to hone in on the broader Internet. While Microsoft launched MSN, Netscape Communications stole the lead on Internet access with the graphical Netscape Navigator. It was Microsoft’s Internet Explorer push to regroup that helped spur the anti-trust investigation.

Years later, to his credit, during a trade show speech, Bill Gates joked that he discovered the Internet (full pause)…after everybody else did.

3. The Vista debacle

Windows Vista was the overhyped successor to Windows XP, which frankly, most people liked just fine. Sometimes called “the Visaster,” it was late to market and when it shipped in 2007, there was no love. It was slow even on high-end PCs and riddled with compatibility issues that broke old applications. And, if you bought it pre-installed on a new computer, you had to fight your way through a sea of junk ware—third-party software also packaged up with the machine.

It was a mess.

4. Mobile.

Microsoft was so desperate to fix its Vista problem that it took its eye off the ball in another area it should have mastered: mobile devices When Apple launched the iPhone in 2007, it started the push to completely transform the phone. Since that time, Microsoft stood by as Android devices vied with iPhones and iPads for market supremacy; Windows phones seem perennially stuck in the “other” category.

This situation wasn’t remedied even after Microsoft bought Nokia’s phone business for more than $7 billion in 2013. It has been trying to recover from that deal ever since.

5. Other product snafus

While the Office applications, Windows and Windows NT (now known as Windows Server) have generated billions for the company, there have been lots of software misfires as well.

Anyone remember “Microsoft Bob?” or Clippy? No? There’s a good reason for that.

But over all of those rather minor misfires, loomed what Muglia referred to as the “file system that rules all.” This started out as a project called “Cairo” which fell apart around 1994, but was followed by another effort, code-named, “Longhorn.”.

Longhorn was to be built around, the Windows File System or WinFS, and promised so many features and functions there was no way it could deliver. It, too crashed and burned, under the aforementioned Vista branding.


Perhaps the best example of an on-stage fail of a Microsoft product came at Comdex, a now-defunct trade show, in 1998 when Chris Capossella, who is now Microsoft’s marketing chief, was on stage with Gates to demonstrate how users would be able to plug new devices seamlessly into a PC running the yet-to-ship Windows 98.

Things didn’t work out that way as you will see below.:


And for even more on early Windows, check out the video of Steve Ballmer’s early ad.

For more from Barb, follow her on Twitter @gigabarb. Read her Fortune coverage at or subscribe via her RSS feed.


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