Happy 30th birthday, Windows: What we've loved through the years

Celebrate three decades of Microsoft's desktop innovation with a trip down 64K memory lane

Happy 30th, Windows: What we’ve loved through the versions
Credit: Omer Wazir via Flickr
Happy 30th, Windows: What we've loved through the years

Love it or hate it, Windows has exerted the single largest influence on one of the most important pursuits in human history. From its floppy disk origins to today’s automagic updates from the cloud, Windows has found its way into every pore of personal computing. And on the eve of its 30th anniversary, Microsoft’s flagship shows no signs of slowing down -- regardless of whether you like where it is going.

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As birthday candles bring with them a whiff of nostalgia, here we highlight the truly glorious advances in everyone’s favorite tech whipping boy -- and there have been many.

But it ain’t all sweetness and light, bucko, so be sure to catch my companion slideshow surveying 30 years of Windows flubs.

Windows 1.01: Amazing that it worked at all
Credit: Wikimedia
Windows 1.01: Amazing that it worked at all

On Nov. 10, 1983, at the Helmsley Palace Hotel in New York, Bill Gates announced Windows 1.0. It didn’t arrive in stores until Windows 1.01 shipped two years later on Nov. 25, 1985 -- establishing a precedent that continues to this day. Notably, Bill Gates told InfoWorld’s Denise Caruso that Win 1.0 was scheduled to ship in April 1984, “but the date has slipped to May.” He didn’t mention May of which year.

Apple shipped the Macintosh in January 1984, and Microsoft was heavily involved in its development. Zealots on both sides love to accuse the other side of stealing ideas. But both Mac OS and Windows owe more to Xerox Star than they do to each other, although the lines of inheritance are blurred. Gates himself seemed motivated primarily by seeing VisiOn for IBM PCs at COMDEX in 1982.

Windows 1.01 ran on top of DOS, and its shaky underpinnings frequently shot it down. But its heart of icons, scroll bars, and non-overlapping windowed gold shows through in this screenshot. Windows 1.01 shipped with an “MS-DOS Executive” (basically, the result of a DIR command), Paint, Windows Writer, Notepad, Calculator, Calendar, Clock, Clipboard Viewer, and a game (Reversi) designed to entice users into figuring out that newfangled contraption, the mouse.

Windows 1.01 cost a mere $100 (in 1985 dollars) and required MS-DOS 2.0 or greater, two double-sided floppy drives, and a graphics card. It took up 256KB of memory, but it worked better at 512KB. The mouse was optional -- and quite expensive. Versions 1.02 and 1.03 ensued, primarily adding various pieces of international support, with the final Windows 1.04 being formally released in April 1987. The line wasn’t officially deprecated until the end of 2001. Yep, Win 1.0 was supported for 16 years.

Windows 2.0, Windows/286 (2.10), Windows/386 (2.10), 2.11: Bundled runtime
Credit: Wikimedia
Windows 2.0, Windows/286 (2.10), Windows/386 (2.10), 2.11: Bundled runtime

Two years after Windows 1.01 shipped, on Dec. 9, 1987, Microsoft shipped Windows 2.0. The company invigorated sales by bundling Windows 2 with new Windows applications, Excel and Word: If you wanted Excel or Word for Windows, you got a runtime copy of Windows 2.0, 286, or 386 to support them. That way, every sale of Excel or Word back then counted as a sale for Windows. Fire up Excel or Word for Windows, and DOS brought up Windows 2.x, then launched Excel or Word on top of Windows 2.x. Exit Excel or Word, and Windows 2.x died.

Windows 2.03 introduced the defining feature of Windows 2: overlapping windows. A new application called Control Panel was introduced. Windows 2.0 could support VGA color graphics -- albeit at 16 bits. Another application, Clipboard viewer, let you see the contents of the clipboard -- a feature that’s sorely missed, even in Windows 10.

Windows 2 also marked the beginning of another Microsoft hallmark: confused, almost pathological, branding. Microsoft released versions of Windows 2 with differing dot-revs that ran on 286 and 386 machines, resulting in mixed-up references to all Windows 2 versions scattered throughout the archives. A definitive rundown on Windows/286 and Windows/386 internals appears in William Hall’s PC Magazine article from Oct. 2005.

All of the Windows 2 standalone versions sold for $100, although many people who ran Windows 2.x received their copy when they bought an application that required Windows -- Excel, Word for Windows, and Aldus PageMaker, among others. (PageMaker first ran on Windows 1.0, but few people tried.) Windows 2, like Windows 1, was supported until the end of 2001.

Windows 3.0: Memory magic
Credit: Deborah Szebeko via Flickr
Windows 3.0: Memory magic

Still bound to DOS at the wrists and ankles, Windows 3.0, released in May of 1990, brought a near-magical ability to use all of an 80286 PC’s memory, unhampered by the old 640KB memory barrier. The new Program Manager and File Manager replaced the DIR-like MS-DOS Executive, with folders replacing directories, and icons for programs. Along with the 2.0 applications, Solitaire appeared. Its creator, intern Wes Cherry, never made a dime from royalties.

Under the hood, David Weise and Murray Sargent figured out how to get Windows 2.0 to run in protected mode, breaking the old 640KB memory barrier. That was the fundamental breakthrough that led to Windows 3. Protected mode let Microsoft write Windows programs that could take advantage of all of a machine’s memory, run “normal” Windows programs in upper memory, and in a related move, create virtual device drivers that could be shared by all running programs. Application developers could build programs that used much more memory without having to manage their own memory allocations.

Device drivers automatically gained multithreading capabilities. Graphic cards that could support it suddenly became capable of displaying 256 colors simultaneously. It was a core golden age.

Microsoft rewrote its bottlenecked routines, changing from C to assembler, and that made Windows 3.0 run like a slow tail wind on a downhill run. Windows 3.0 also brought the Win32 API, giving developers solid hooks into the OS.

Most people who bought Windows 3.00a with Multimedia Extensions 1.0 (Oct. 1991) got it bundled with a shiny new CD player and a sound card. Ka-ching. Microsoft’s first Entertainment Pack for Windows gave us Minesweeper (by Robert Donner and Curt Johnson), Tetris (by Dave Edson), and a Mahjong variant known as Taipei. All told four Entertainment Packs were released, at $40 each. Ka-ching. Ka-ching.

Windows 3.0 fetched $150, or $80 for an upgrade. Microsoft sold more than 4 million copies of Windows 3.0 in its first year. As Brian Livingston explained in the Oct. 21, 1991, issue of Computerworld, “Today, a company with no PCs that run Windows is almost like a company without a fax machine.” Imagine that. Ultimately, Win 3.0 hit 10 million copies. Microsoft became the richest software company in the world.

Support for Windows 3.0 ended at the end of 2001.

Windows 3.1, Windows for Workgroups 3.11: Big times and nascent networking
Credit: Wikimedia
Windows 3.1, Windows for Workgroups 3.11: Big times and nascent networking

Windows 3.1, code-named Janus, arrived in April 1992 greatly improved and designed to take on IBM’s OS/2 head-to-head. Good-bye 8086; hello 80286, at a minimum, with full support for 80386 Enhanced Mode. Icons could be dragged and dropped. Multimedia was built into the system. The Registry made its first appearance, forever sealing advanced users’ doom. In exchange, Windows 3.1 users got Minesweeper at no additional cost.

Steve Gibson, writing in InfoWorld, noted that Microsoft sold 3 million copies of the Windows 3.1 upgrade within two months of launch, calling it a “strong success.”

Having mowed over the consumer market, Microsoft turned to businesses, rolling peer-to-peer networking and a handful of utilities into the mix. Windows 3.1 for Workgroups consisted of Windows 3.1, packaged with real mode networking software and a few utilities. Windows for Warehouses (as we deridingly called it) didn’t flourish until Microsoft was able to move the networking pieces into upper memory, freeing the lower 640KB for “regular” programs.

In Aug. 1993, Microsoft released Windows for Workgroups 3.11, a full-fledged (if at times very frustrating) networking operating system and come-from-behind competitor to the then-dominant Novell NetWare. WfW 3.11 required heavy iron -- at least an 80386SX processor -- but offered remote configuration, Remote Access Services, its own file system and cache, and later, a downloadable TCP/IP stack called Wolverine.

TrueType: The font plot thickens
Credit: Wikimedia
TrueType: The font plot thickens

Windows 3.1 brought TrueType, a new technology that changed the face of modern computing.

I’ll never forget the first time I bought a font. I paid Adobe $119 for a copy of the Tekton font family. Hard to believe that Windows-addled font fanatics like me used to shell out amounts like that for a font -- even for a gorgeous typeface from David Siegel.

Of course, TrueType wasn’t even developed by Microsoft. It started as a feature of Mac OS 7, in May 1991, to wrest control of the digital font world from Adobe. Apple wasn’t interested in paying for Adobe PostScript Type 1 font licenses for every LaserWriter sold -- even though Apple owned a 15 percent stake in Adobe at the time.

Bill Gates introduced TrueType during the Seybold conference in 1989. Adobe co-founder, PostScript co-inventor, and former Xerox PARC employee John Warnock followed Gates on stage, calling the TrueType effort “the biggest bunch of garbage and mumbo jumbo.... These people are selling you snake oil.”

Snake oil it may have been, but TrueType found a home in Windows, and it’s been a cornerstone ever since.

Windows NT: Once again, from the ground up
Credit: Microsoft
Windows NT: Once again, from the ground up

In Aug. 1988, Bill Gates hired Dave Cutler, head architect of DEC’s VMS operating system, and 20 of Cutler’s closest engineering friends to build the next version of IBM’s OS/2. What resulted were two efforts: one that produced Windows 3.1, and the other, a ground-up rewrite of Windows that finally liberated Windows from its shaky DOS roots.

Windows NT 3.1 shipped in July 1993. There were two versions, Windows NT Workstation for the high-end client market, and Windows NT Server for the corporate server market. With NT, Microsoft made the strategic decision to stick with the Win32 API, albeit in a modified form.

Windows NT wasn’t designed to appeal to the masses. It was designed to free Windows from the chains of DOS. Aside from copious problems with drivers that had to be rewritten and a few problems around the edges, NT was (and is) solid as a brick. NT brought a host of well-planned features, including Group Policy, the NTFS file system, BitLocker, Windows Update, and Hyper-V. It also introduced Active Directory, a feature that’s kept tens of thousands of admins fully employed for a couple of decades.

In July 1996, Windows NT 4, which followed Windows 95 chronologically, brought us the DirectX multimedia API, native font anti-aliasing, the “My” terminology (“My Documents”), high color icons, full window drag, Task Manager, the Blue Screen of Death, and many of the Windows 95 programs, including the pinball game Space Cadet from the Windows 95 Plus! Pack. NT 4 moved graphics and printer drivers into the kernel, to speed things up, and that created endless headaches for driver stability.

Windows NT became the starting point for Windows 2000.

Windows 95: Start me up
Credit: The Mother of all Windows 95 books
Windows 95: Start me up

Anybody who lived through the ads remembers the Rolling Stones' endorsement of Windows 95 -- the “Start me up” campaign in Aug. 1995. Paul McNamara, writing in the June 29, 2011, issue of NetworkWorld, quotes Microsoft COO Bob Herbold as saying that Microsoft paid about $3 million to use the song, although rumors at the time ran from $8 to $14 million.

Microsoft legend Brad Silverberg ran the engineering team, and Brad Chase ran marketing. Together, they created the “perfect storm” -- a product welcomed and loved all over the world. Win95 sold more than a million copies in four days, at $90 a pop, 40 million copies in its first year. Would-be testers shelled out $20 to join the Preview Program.

Stephen Manes at the New York Times famously declared: “In many ways this is an edifice built of baling wire, chewing gum and prayer, but you will probably end up living there.”

The list of innovations in “Chicago” goes on and on: The Start button, Start menu with cascading submenus (missing in Windows 10), Plug and Play peripherals, the task bar, fully fleshed out Win32 API, long file names, a much improved UI with shortcuts, notification area, volume control, Program Manager, Active Desktop, Windows Explorer. The service packs brought new features: Internet Explorer 3 and then 4, FAT32 file support, DirectX, and USB features.

But it still ran on DOS, and it still suffered from DOS stability blues.

Microsoft dropped support for Windows 95 at the end of 2001.

Windows 98, 98SE and ME: Say goodnight, DOS
Credit: Microsoft
Windows 98, 98SE, and ME: Say goodnight, DOS

One of Microsoft’s pivotal power struggles found its way into Windows 98, and it resonates to this day. A confrontation between Jim Allchin and Brad Silverberg resulted in Microsoft’s commitment to moving Windows to the Internet waning and its focus on traditional PCs and networks expanding. Allchin wanted IE integrated into Windows. Silverberg wanted a separate IE, capable of working on other platforms, and not tied to the Windows ship cycle. Allchin won, Silverberg left, and the result can be seen directly in Windows 98, 98SE, ME, and 2000.

In June 1998, Windows 98 rolled in all Win95’s OSR improvements and added Task Scheduler, System File Checker, multiple monitor support, and hibernation for the first time. Dubbed the “first version of Windows designed specifically for consumers,” Win98’s new Quick Launch toolbar improved the interface slightly, but other consumer-oriented improvements (other than 3D Pinball) were sparse. Win98 integrated Internet Explorer 4.01, which led to the U.S. v Microsoft antitrust case.

Less than a year later, Microsoft released a barely improved Windows 98 SE, best known for its inclusion of IE5 and Internet Connection Sharing, which allowed one PC to share its Internet connection with others on the network.

Windows ME (Millennium Edition) was the last version of Windows based on DOS -- truly a triumph. Notably, notoriously, Windows ME introduced Automatic Updates into the Windows lexicon. The rest, as they say, is hell, er, history.

Windows XP: DOS and NT pedigrees finally melded
Credit: Nick Perla via YouTube
Windows XP: DOS and NT pedigrees finally melded

Skipping lightly over Windows 2000 (Microsoft’s first attempt to use the NT kernel on a general-purpose machine), we arrive at one of Microsoft’s stellar accomplishments, Windows XP. More accurately, XP (Oct. 2001) was the precursor to one of Microsoft’s true stellar accomplishments, XP Service Pack 2 (Aug. 2004). XP was the premiere version of Windows for five and a half years, and it was supported for almost 14 years.

Windows XP brought a bundle of new features, including a new cascading Start menu, ClearType subpixel rendering, better handling of taskbar icons, fast user switching, Shadow Copy, System Restore, Remote Assistance, Remote Desktop, Windows Media Player, Windows Movie Maker, and a more adaptable Windows Explorer with native Zip file handling. It was faster and far more stable than the DOS-based Win 9x series. The first version of XP was bundled with IE 6, Outlook Express 6, and Windows Messenger. Windows XP also started us down the road of validation and the “genuine” experience.

Windows XP Professional added the ability to join a Windows domain, Remote Desktop server, Encrypting File System, Offline files and folders, Group Policy editor, and a handful of more esoteric features.

Bill Gates, looking at the sorry state of Windows XP security, instituted his Trustworthy Computing initiative in Jan. 2002. The initiative directly led to a massive walkthrough of XP code and the re-issuing of XP as what we now call Windows XP SP2. The Trustworthy Computing Group closed down in Sept. 2014.

Other XP versions have thrived in niche markets, while Windows XP itself became nearly ubiquitous, selling 17 million copies in its first two months, according to Microsoft. Ubiquity, however, made XP a massive target for malware. SP2 addressed the security problems but didn’t solve them. IE6 grew a popup blocker, but also rolled out ActiveX, which became a magnet for attacks.

Windows 7: Less is more
Credit: Windows 7 All-in-One for Dummies
Windows 7: Less is more

The struggle to get Windows 7 out the door spanned a major reshuffling of troops, negative reactions to Vista, enormous pressure to not upset drive compatibility, and a dev team of about a thousand programmers.

Steve Ballmer tapped Steve Sinofsky to rescue the project. Fresh off repeated successes with Microsoft Office, Sinofsky moved his entire management team to Windows 7, turning out a highly respected product in three years, in Oct. 2009.

Win7 introduced all sorts of innovations: Libraries, HomeGroups, federated search, significant improvements to the Start menu and taskbar -- which shows thumbnails and jump lists -- Aero snap, desktop gadgets, themes, better access to the Devices list, major DirectX improvements, big performance improvements, solid-state-drive support, many more multimedia formats, a Windows XP Mode that actually works, and much more.

One of the best innovations: Windows Live. Microsoft realized the Win7 effort was being weighed down by the development of add-on programs that could easily be distributed independently of the OS. Four applications in Vista -- Windows Mail, Calendar, Movie Maker, and Photo Gallery -- were yanked and relegated to downloadable status on the Windows Live website. Microsoft abused the Windows Live moniker for years, but the idea of separating Windows from the apps -- and updating each independently -- became a key strategy in Windows 8 and 10.

Windows 7 SP1, released in Feb. 2011, has become the Windows version to beat.

I never trusted any Windows 7 sales figures, but two years after launch, it was on roughly half a billion machines.

Windows 10: A truly mixed bag
Credit: Windows 10 All-in-One for Dummies
Windows 10: A truly mixed bag

Windows 10 version 1511 (aka the Fall Update, TH2, or build 10586) shows lots of innovation, but the jury’s still out on whether Win10 will become as usable as Win7. Problems with forced updating, undocumented patches, tracking, and unwanted advertising have many Windows 7 customers wondering which way to jump.

The triumphs of Windows 10 are attenuated by the uncertainties. They’re also, by and large, works in progress, with promised fixes still in limbo.

Windows 10 manages to meld the Win7 Start menu with the Win8 tiled interface, keeping most of the touch-friendly features of Windows 8. Its new browser, Microsoft Edge, may someday be useful: The fact that it’ll knock IE into obscurity is its single greatest redeeming factor. The voice-activated personal assistant Cortana holds great promise, but seems limited so far. Windows Hello will make sign-in authentication more secure than ever, if we can get the hardware working right. Continuum remains more of a buzzword than a product, but some day we’re assured we’ll be able to take our phones to a docking station and have all the comforts of home.

The Win10 Universal apps -- Win7 gadgets all grown up -- are slowly getting better. OneDrive is still a huge disappointment. The three Skype apps work, but they’re not as good as the phone versions. Mail and Calendar work -- finally. Groove Music and Movies & TV are still primed to convince you to spend money. And so on. The Windows Store is still a wasteland, but there are occasional signs of life.

The others
Credit: Microsoft
The others

What, you may ask, about Windows Vista, Server 2000/2003, Windows Home Server (my favorite), and Server 2008/2012? Here’s a quick overview of the key triumphs in each:

Windows Vista (Nov. 2006) brought the Windows Aero GUI (which I still prefer, so shoot me), security improvements (remember User Account Control?), Windows Calendar, DVD Maker, and IE7. None of those are particularly noteworthy, let alone “triumphs,” and Vista itself had all sorts of problems.

Windows Server 2000 implemented Active Directory, Terminal Services, and several Win98 features, while Server 2003 brought improved security and, with 2003 R2, tools for managing branch offices.

Windows Home Server brought many server functions to lightweight servers, such as automatic backup and restore, file duplication, and media sharing.

Windows Server 2008 incorporated Vista’s improvements and, with 2008 R2, many of the features in Win7. 2012 took a detour to the Win8 tiled side, but 2012 R2 seems to be back on track.

And with that, a big happy birthday to Microsoft Windows. Here's to many more.