The worst: Bottom five moments in Windows' 25 years

Windows turns 25 tomorrow, and there have been a lot of lowlights during that time. Here's my list of the worst of Windows for last 25 years, in chronological order. For a more complete look at the history of Windows, check out my article Visual Tour: 25 Years of Windows. For a look at the best of Windows, check out my blog post The five best Windows moments of the last 25 years.

Microsoft admits it falsified testimony about Windows in anti-trust trial

Microsoft was being prosecuted by the U.S. Justice Department for anti-competitive anti-trust behavior for a variety of reasons back in 1999. The Justice Department claimed that Microsoft was using monopoly power to quell browser competition to Internet Explorer. One of Microsoft's main defenses was that Internet Explorer was an integral part of Windows, and could not easily be uninstalled, and so it had no choice but to push Internet Explorer onto people's desktops.

To make its point, during the trial Microsoft played a taped demonstration, supposedly showing that removing Internet Explorer from Windows caused system instability and slowdowns. There was only one problem with that tape though: It had been altered by Microsoft. Prosecuters notice the alteration, and Microsoft had to admit during the trial that it in fact had altered the demo.

Then, a week later, it happened again, with a tape claiming to show that it was easy for America Online users to install Netscape Navigator on their Windows desktops.

Windows ME

If 1999 was a bad year for Windows because of the anti-trust trial, 2000 may have been worse. Windows Me was released in September, 2000, and was immediately reviled by many. It was buggy, plagued by installation problems, and had many hardware and software incompatibilities. Many people still believe that it was released only for marketing purposes, because less than a year later, Windows XP was released.

Windows Vista

Many people consider Vista the worst Windows operating system of all time. It had a plethora of hardware and software incompatibilities, it wouldn't run on older hardware, and there were plenty of complaints about its resource-hungry user interface.

Windows Vista lawsuit

In February 2008, embarassing Microsoft internal documents were released, in the Vista "junk PC" lawsuit. The suit claimed that Microsoft had misled consumers into buying Windows XP computers marked "Windows Vista Capable," even though the PCs couldn't run the most important features of the then-new Vista.

The released documents are among the most embarassing moments in Microsoft history. One, from an unnamed employee, wrote in an e-mail, "Even a piece of junk will qualify" to be called Windows Vista-capable. And in another e-mail message, Mike Nash who was a Microsoft executive at the time, wrote, "I PERSONALLY got burnt.... Are we seeing this from a lot of customers?... I now have a $2,100 e-mail machine."

European Union fines Microsoft $1.2 billion for Windows anti-competitive behavior

February, 2008 would proved to be the cruelest month for Microsoft. On February 27, the European Union handed Microsoft a record fine of $1.3 billion for anticompetitive behavior. They slapped the fine on the company for violating a 2004 agreement to curb anticompetitive behavior relating to Windows.

In issuing the fine, Neelie Kroes, the EU's competition commissioner, said, "Microsoft was the first company in 50 years of EU competition policy that the commission has had to fine for failure to comply with an antitrust decision. I hope that today's decision closes a dark chapter in Microsoft's record of noncompliance with the commission's March 2004 decision."

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