Top 5 Windows Editions

A Brief History of the Most Important Microsoft OSes

Windows is over 25 years old now. It a good time to look back on the five most important Windows releases of all time. Note that this isn't a list of the best Windows releases, but rather the ones that were most important, for whatever reason. It's been a long, strange trip, Microsoft.

1. Windows 95. This may come as a surprise to many. But Windows 95, released in August 1995, is when the public truly started embracing Windows.

Microsoft put on a gigantic public-relations blitz for Windows 95, highlighting the "Start" button that has since been used in every version of Windows, unveiling it to the tune of the Rolling Stones' "Start Me Up." Perhaps in an ominous sign of things to come, Microsoft co-founder Bill Gates suffered through a Blue Screen of Death during one Windows 95 demo.

Windows 95 was Microsoft's first true GUI (Graphical User Interface), which it layered on top of DOS (Disk Operating System). It made Windows much more accessible to the average user and helped launch Windows' dominance in the market.

2. Windows XP. Chances are good that the majority of you are reading this on a Windows XP computer, and that's why it's second on this list. Windows XP, released in 2001, still has nearly 59 percent market share. This, for an OS nine years old, speaks to how good XP is.

Originally taking some hits for what some called its "Fisher Price interface", XP was an immediate success.

It wasn't until SP, or Service Pack, 2, that Windows Firewall, the primary security tool, was enabled by default. This contributed in part to Microsoft's reputation of building insecure products. But despite its flaws, XP had many more advantages, which accounts for its remarkable popularity.

3. Windows 98. The chief claim to fame of Windows 98, released in June 1998, was that it got Microsoft in hot water with Uncle Sam.

Windows 98, the successor to Windows 95, was bundled with Internet Explorer, Microsoft's Web browser. An innocent-seeming move, right?

Wrong. The U.S. Justice Department contended in court that bundling IE was an unfair decision, designed to kill competitors like Netscape, at that time the dominant browser on the market. In essence, every computer that came with Windows 98 had a built-in browser, so why download Netscape over the Internet? The government won the case, and Microsoft had to make major changes to how it built OSes and did business. All because of a little browser.

4. Windows 7. If you've spent any time on this site at all, you know how much I love Windows 7. It's Microsoft's best OS ever, and nothing else is really close. It's also Microsoft's fastest-selling OS, and within a year or so overtake XP as the most popular OS. That's a good thing because Windows 7 is significantly more secure and user-friendly than any previous Microsoft OS.

Released Oct. 22, 2009, Windows 7 has a completely different look and feel than other OSes. It also has the best networking features, built-in touchscreen functionality, better backup and recovery tools, and quicker startup and shutdown times.

In short, Microsoft got it right with Windows 7.

5. Windows Millennium Edition. Did you shudder reading that name? If so, it means you probably owned a copy. Windows Millennium Edition (or Mistake Edition, as many called it) was full of more holes than an aerated lawn and more insecure than Stuart Smalley.

Microsoft unleashed Windows Me on an unsuspecting world in September 2000. It quickly and correctly gained a reputation as a buggy, crash-prone, vulnerable mess. Consider just this one little nugget: If your computer crashed because of a virus, worm or other malware, and you performed a System Restore to bring it back to life, Windows Me would often re-install the malware that caused the crash in the first place.

Hard to believe, but true.

So why is it ​no this list? Because Windows Me was so hideous that it forced Microsoft to replace it, less than a year later, with Windows XP. Microsoft learned many lessons about how not to build an OS from the Windows Me debacle.