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A Visual History of Windows

Over its 40 years, PCMag has covered every version of Microsoft's operating system. Like you, sometimes we loved it, and sometimes we didn't. Let's take it back to MS-DOS to see how Windows has evolved.

PCMag has covered Microsoft's Windows operating system from its first iteration in 1985 right up to the current, heady days of Windows 11. Before Windows, we used and wrote about its predecessor, MS-DOS (Disk Operating System), without which the PC revolution would never have taken place. Indeed, early mentions of Windows in PC Magazine refer to it as a "DOS extension from Microsoft."

When I began working at PCMag in 1987, DOS was still king, having pretty much kicked CP/M to the curb. DOS itself had been getting increasingly if awkwardly graphic, using character dots to create images and offering more colors than drab blue-gray text on black. At the time, I was a proofreader at the magazine, a position so low on the masthead that it hasn't even existed for decades. I didn't really think much about Windows until around version 3.0.

The Origins of Windows

Of course, Microsoft had seen what Apple was doing with the graphical user interface (GUI) of its early computers, starting with the Apple Lisa. The Lisa debuted in 1983 and was inspired by work at Xerox's Palo Alto Research Center (PARC). It was followed by the company's first successful GUI machine, the Macintosh, a year later. Third-party GUIs became a big topic for DOS in the mid- and late 1980s, albeit slowly. Windows started out as just another one of those graphical shells that ran on top of DOS.

In PC Magazine's Best of 1985 article, we said, "Most industry watchers declared Microsoft Windows stillborn the day IBM rolled out TopView [a 1985 flash in the pan]." Shows what industry watchers know. The article continued, "Like the host who continues to hang decorations for a party nobody plans to attend, Microsoft has continued development work in a way that seemed stubbornly futile." Finally, though, we admitted that improved graphics hardware and compelling application titles brought Windows back into relevance: "After an hour with In-a-vision [the first native application to be offered for Windows], even the most devoted Macintosh user will be a convert."

To be honest, the launch of Windows 1.0 was nowhere as big a deal in my recollection as the launch of the now-forgotten PS/2 port, found on IBM's then-new Personal System/2 desktop line. (At I write this, there's a PS/2 for sale on eBay for $350, and it still works; the original price was $2,295.) As it turns out, IBM's plan to recapture the PC market from cheaper clone makers by including proprietary BIOS, expansion-bus, and other technologies backfired big time.

PC Magazine Microsoft Windows cover from 1985
The first mention of Microsoft Windows on the cover of PC Magazine was in 1986 (left), but it didn't get top billing until 1991 (middle). The first cover-story review was for Windows 3.1 in 1992 (right).

Even nearly four years after the 1985 launch of Windows, it was just another entry in our September 12, 1989 issue's face-off of GUI competitors including HP NewWave, DeskMate, and GEM (possibly the highest-profile of the lot). IBM's TopView actually made the cover in April 1985, while Windows didn't receive that honor until 1991. Even Microsoft Excel merited a PC Magazine cover story in 1987, before Windows ever did.

The first mention of Microsoft Windows on the cover was for a February 25, 1986 roundup of alternative operating environments for DOS in a story titled "Window Wars!" It covered such options as GEM Desktop, TopView, and DESQview as well as Windows 1.0. Starting with Windows 3.1 in 1992, every major Windows version made the cover, though DOS 6 was still there the following year.

And let's not forget a rival operating system from IBM called OS/2, which showed up in 1987 and most tech experts considered superior to both DOS and Windows. But such is the power of market popularity over technical superiority.

Windows Starts Winning

The first really big splash Microsoft's OS made came a full 10 years after its debut, with Windows 95 (codenamed "Chicago"). This was a huge deal accompanied by a worldwide publicity campaign. You can watch the 90-minute Win 95 launch event, hosted by Jay Leno, on YouTube.

This version introduced the Start button (commercials featured the Rolling Stones tune "Start Me Up"), plug and play, and much more, as you'll see in the pictorial history below. It also spelled the end of an era for DOS, which until then had been a separately available operating system. Windows 95 appeared on the cover of PC Magazine no fewer than four times. It kicked off the basic look and feel of the OS that would last to some extent until Windows 8 in 2012.

PC Magazine covers featuring Windows
Windows 95 made the cover of PC Magazine four times. After that, every big release was a cover story.

Windows 95 also implemented big changes to the operating system core, including a move from 16-bit to 32-bit architecture and preemptive multitasking. Of course, server versions of Windows were also in development. Windows NT remains a major milestone and the basis of most versions even to Windows 11, having replaced the underlying DOS core.

The Evolution of a Software Powerhouse

In the years that followed Windows 95 and its not-very-different successor Windows 98, new releases tended to follow a rocky pattern based on public opinion:

  • Windows 95/98—Good
  • Windows Me—Bad
  • Windows XP—Good; many users clung to it even through the dark days of Windows 8
  • Windows Vista—Bad (though I dispute this; I found Vista one of the most stable versions ever. The complaints were mostly about hardware compatibility due to a move to a more secure driver model.)
  • Windows 7—Good
  • Windows 8—Disastrous (it nearly ended the OS, though it did add a few useful features)
  • Windows 10—Good (and well-received)

With Windows 11, it seems like Microsoft is finally breaking that back-and-forth. In truth, the latest version is mostly a pretty shell on top of Windows 10, with appealing sounds, some new apps, and other conveniences thrown in. I didn't personally start reviewing Windows until Windows 7 in 2009. It, and the next two releases, involved traveling to Los Angeles and Seattle to be pre-briefed. Windows 7 turned out to be the last cover story ever for the print version of PC Magazine in January 2009. After that, PCMag became online-only, which was one of our best business decisions—not only because that was the direction the world was heading, but also because the price of paper soon skyrocketed.

PC Magazine covers featuring Windows
Windows 7 headlined PC Mag's last print cover in 2009 (left). More recent versions of the OS starred in our digital editions.

Windows 8 was the most disastrous release in franchise history, though it sounded great in pre-briefs: Windows would challenge the Apple iPad as a tablet OS while still running on desktops and laptops, and its app store would be a bonanza for developers! Scratch that. Though the 8.1 update fixed a lot, the company had to reverse course. Microsoft skipped version 9 entirely, needing to create more distance from the hateful 8. Even in the PCMag offices, I was the only one running Windows 8 for a few years, and actually enjoyed using it after the Windows 8.1 update. I was mostly alone in that.

The familiar-looking yet more modern Windows 10 reversed the platform's downward course. Since then, there have been no more blockbuster launch events, as the software-as-a-service system has taken hold. Indeed, remarks from Microsoft execs made observers think there'd be no more new versions after Windows 10, so Windows 11 was something of a surprise. It adds polish and modern style as well as some new tools and conveniences, but it doesn't break with tradition dramatically.

Scroll through our visual history to see how far Windows has come from its sketchy starts, stops, and restarts.


MS-DOS

MS-DOS
MS-DOS

As PC Magazine described it in its February-March 1982 issue, "MS-DOS is a single-task microcomputer disk operating system for the Intel 8086 and 8008 microprocessors."

With MS-DOS 2.0, Microsoft replaced "the traditional command-line-oriented shell with a visual shell that shows the user a menu of the most commonly executed applications and utilities," we said at the time. DOS carried on for a few years even after Windows arrived, and it formed the underlying foundation of early versions of Windows.


Windows 1.0

Windows 1.0 Start Screen
Windows 1.0 Start Screen

The first version of Windows, 1.01, arrived in late 1985, but it was not the only OS in town. "Window Wars!" screamed PC Mag's February 1986 cover. We compared Redmond's OS to GEM Desktop, TopView, and DESQview, and admitted that the Mac made "the PC's display look like a relic from the past."

Windows 1.0 Desktop
Windows 1.0 Desktop

Windows "puts a new face on DOS and uses DOS to do some work," we said. Rather than using only a single command line on screen, Windows "puts the entire screen to work passing information between you and the computer." Applications included Paint, Calculator, Cardfile, Notepad, Terminal, and Write. One complaint about Windows 1.0? The mouse (or "all-purpose pointing device," as we called it in 1986), which was not yet a common, indispensable PC tool.


Windows 3.0

Windows 3.0
Windows 3.0

After an unsuccessful split version of Windows 2.0 (sold in both 286 and 386 iterations), Microsoft hit its stride with Windows 3.0 in 1990. "The most noticeable improvements to Windows 3.0 are its interface, sculpted buttons, and an iconic layout that makes it easier to execute commands and manage files," we said in June 1990. "Using a file-folder visual motif, icons and applications are set up as members of common-sense categories." Windows 3.1, introduced in 1992, added TrueType fonts, screen savers, Windows Media Player, and a sound recording app, while Windows 3.11 for Workgroups added integrated networking support.


Windows 95

Windows 95
Windows 95

Windows 95 made the cover of PC Magazine in September 1995. Seventeen PC Labs analysts and technicians tested the software for 10 weeks to see whether it would be your next OS. "The Windows 95 interface offers a true desktop with icons for programs, documents, directories, and system components. Context menus, accessed by right-clicking, give you the relevant actions and properties for any object."

"Friends" stars Jennifer Aniston and Matthew Perry even made a slick instructional video for it.


Windows 98

Windows 98
Windows 98

Windows 98 arrived in 1998 and included a number of Web-related features to take advantage of the internet explosion. It didn't look a lot different from Windows 95, but it did include this sweet, Zen-like startup sound.


Windows 2000

Windows 2000
Windows 2000

Windows 2000 added support for layered windows and translucence. "Television does a great job of using fades and slides to give a context of where the new information is going to appear. Computers haven't yet been able to incorporate these effects into the UI very effectively," Microsoft said at the time. "Just think what a difference there is between the existing UI and the cool UI you constantly see in the movies. Layered windows give the product designers a lot of power to bring 'cool' UI closer to reality."


Windows XP

Windows XP
Windows XP

"Windows XP is Microsoft's latest—and dare we say greatest—operating system to date," we said in 2001. "The most startling change" with XP was the revamped user interface: "Windows XP drastically reduces clutter on the desktop, Start menu, and taskbar. The new design is Microsoft's effort to make Windows less confusing to beginners."

Windows XP Start Menu
Windows XP Start Menu

"The new two-column Start menu," we added, "reduces the clutter that plagued earlier versions and highlights Microsoft's software."


Windows Vista

Vista Welcome Center
Windows Vista Welcome Center

"Vista offers a lot of improvements over Windows XP, but most of them are conveniences rather than essentials," PC MagazinePC Magazine concluded in 2007.

Vista's "Flip 3D" view allowed for easy application-switching. Press Windows-Tab or click the "switch between windows" Quick Start icon, and open windows morphed into this perspective view. Rotating the mouse wheel spun the stack of windows, Rolodex-style. Vista's live icons provided a preview of what was inside folders.

The Welcome Center appeared when you first booted. Above, you can see what it looked like on top of Vista's Aurora wallpaper.


Windows 7

Windows 7 desktop
Windows 7

"Microsoft's new OS is a big improvement over Windows Vista, and because it's based on the same underlying kernel code, there should be fewer compatibility headaches for those who make the switch," we said in 2009. "Add to that a retooled taskbar, simpler home networking, faster startup, and more, and Windows 7 may succeed where Vista failed."

Windows 7 included a big taskbar update for managing active apps and launching those that you used frequently. Vista had a thumbnail preview system, but Windows 7 added the full-screen transparency Aero Peek feature to reveal your desktop.


Windows 8

Windows 8
Windows 8

Microsoft is the first to admit that it missed the boat when it came to mobile, and the company tried to make up for lost time with the touch-centric Windows 8. The operating system featured a dual interface, one with mobile-like apps and another more like the traditional Windows desktop.

Much to the chagrin of Windows traditionalists, the Start menu was nowhere to be found in Windows 8, replaced by Charms that slid out from the side. The Windows 8.1 upgrade addressed some of the shortcomings for desktop users, but by then, the version's reputation as a loser was sealed.


Windows 10

Windows 10
Windows 10

Redmond skipped Windows 9 and launched Windows 10 as its "most comprehensive platform ever." The Start menu was back in a brilliant synthesis of tiles, buttons, and menu elements (see the video below). The release also added the Action Center and a highly functional Taskbar. Check out a few other reasons that the OS went on to be installed on more than a billion devices.


Windows 11

Windows 11 interface
Windows 11

After Windows 10's software-as-a-service model made it seem as if there would be no more major OS versions—and there weren't for six years—Windows 11 came as something of a surprise.

More of an interface redesign than a new operating system, its round-cornered windows and centered taskbar were arguably mostly aimed to staunch the trickling of market share to Chrome OS and macOS. Still, we really like it. For a full rundown, read our comprehensive Windows 11 review.

About Michael Muchmore