Bill Gates: top ten greatest hits (and misses) - the Microsoft years

Damn, Bill, you have come a LONG way. Look at you there back in '82, you handsome devil. As part of our tribute, let's take a quick look back at the top ten greatest (and not so great) products created on Bill-time, shall we? Don't worry, it'll only sting a little.


Internet Explorer (IE)
Introduced 1995

It's really easy to simply remember "Internet Exploder" as the standards-breaking, web-forking, buggy, monopoly-causing app that helped shape Bill's old image as the evilest baron of all technology companies. But it's also the app that led to the creation Ajax-based web apps through the XMLHttpRequest spec, and the kludgey early popularization of CSS. Love it or hate it, IE's gotten more people on the web over the years than any browser, and that's definitely got to count for something.

Media Center
Introduced 2002

Despite TiVo's DVR dominance and competitors that came and went over the years, Media Center has always been an underrated standout product. Even Bill admits that the company's long struggled with usability, but Media Center is a beacon of hope not only for 10-foot UIs everywhere, but also for the company's ability to create powerful, advanced, user-friendy products. Between its online integration, extensible plugin architecture, ability to stream shows to nodes around the house, and now CableCARD support, the only real downside to Media Center is the fact that you still need a full-blown PC to run it.

Introduced 1981, discontinued 2000

It was arcane and nigh-unusable to mere mortals -- but the early cash-cow was one of Bill's most strategic moves, and helped Microsoft define the concept of software licensing. It also helped launched Mossberg's career as crusader of user-friendly technology. But most importantly, MS-DOS was still the OS an entire generation grew up learning, so del crticsm.* for a second because our autoexec.bat and config.sys were so very well crafted, and extensively tweaking Memmaker for a few extra KB of usable RAM definitely ranks amongst our top most formative geek moments.

Introduced 1989 (on Mac), 1990 (on PC)

Word, Excel and PowerPoint certainly did well enough on their own, but when Microsoft combined 'em into the tidy (and pricey) package that is Office -- first on the Mac in 1989, interestingly -- it had a selling point that would prove irresistible to many a productivity-obsessed middle manager even today. The addition of Outlook and its support for the (for some) nigh-indispensable Exchange only further solidified its foothold in the corporate computing world, and that's where Bill knew the real money was. That's certainly not to say that it hasn't been without its share of problems and annoyances, though -- we're looking at you, Clippy.

Introduced 1982

Microsoft has always been a software company first, but it's been cranking out high-quality peripherals for over 25 years -- long before the Xbox and Zune were even a twinkle in Bill's eye. Not only that, but it's been a reliable innovator in the field, with a string of devices that were first, early, or just simply popularized technologies like the wheel mouse, force-feedback joysticks and controllers, the modern optical mouse, and the ergo-keyboard. The division has gone through some bumpy times -- the SideWinder line was killed off for a while there, and there've been some questionable designs along the way -- but it's been riding high as of late, and it doesn't show any signs of slowing down soon.

Windows 3.1 / NT 3.5
Introduced 1992 and 1994

It took a few versions to come into its own, but by the time Windows hit 3.1, Microsoft finally had a product that was able to pull PC users away from the command line (for some of the time, at least) and give them a real taste of things to come. Windows NT may not have had quite the same appeal with the average consumer, but it did bring the operating system into the 32-bit world and pave the way for enterprise desktop computing as we know it today. (Plus, it had the NT file system (NTFS), which to this day continues to carry on the legacy in its own little way.) We really wish they'd made a sequel to the Pirates of Silicon Valley, because we'd love to have seen the dramatization of Bill overseeing the first popularized verions of Windows -- especially '95, which came out just a couple of years later.

Windows 2000 and XP
Introduced 2000

When thinking of Microsoft and the new millennium, few people are able to keep the crinkles out of their nose. Thankfully, Windows ME wasn't the only thing that arrived in late Y2K, as Windows 2000 rushed in to rock the socks off of suits everywhere. The whole Win2K thing went over so well that Gates and company decided to base its next consumer OS, XP, off of it. Some may argue that the resulting product still stands as the last great OS to ship out of Redmond.

Windows CE / Mobile

Introduced 1996

As two of the most ubiquitous projects to come out from under Bill's command, both Windows CE and Windows Mobile are almost impossible to avoid when it comes to handhelds or phones. What began as a mishmash of small components has grown into the adaptable -- though sometimes maddening -- mobile OS that resides on just about every kind of device you can think of. Really, we mean every kind of device, from PMPs to enterprise-level stock-keeping systems. The slimmed down and restructured micro-Windows is at the very least one of the more flexible offerings the company has ever produced. Say what you will about its usability, there's no denying the massive impact it's had on portability and convergence.

Xbox and Xbox 360
Introduced 2001 and 2005

Back in 1999, Bill was all about multimedia convergence, and he said that a new gaming / multimedia device would be Microsoft's trojan horse into the world's living rooms with something coined the "DirectX-box." In 2001, the original Xbox entered gaming territory dominated by Sony's PlayStation with Nintendo's N64. But the clunky machine brought with it the first easy to use multiplayer console service, Xbox Live, as well as a developer-centric model that helped turn the tables. Of course, things look quite a bit different today: the Xbox 360 leads the former market leader's PlayStation 3 in spend and attach rate, and with the relative success of media and content sales on Xbox Live, it seems Bill's dream of dominating the living room wasn't just a pipe-dream after all.

Visual Basic
Introduced 1991, discontinued 1998

It's hard to underestimate the impact of Visual Basic. While the average user might have never heard of the original VB that Microsoft released way back when, the simplicity of the language and its graphical toolset made just about any power user a potential app developer, powering the flood of third party application development Microsoft operating systems enjoyed throughout the 90's. Sadly, Visual Basic met its demise at the hands of more modern languages and toolsets, but with a legacy of making programming accessible to the masses, its place in the history books and in Bill's pocketbook is undoubtedly secure.

Runners-up: DirectX, Flight Sim, Portable Media Center, Solitaire and Minesweeper


Auto PC
Introduced 1998, discontinued 2001*

Riding high on its previously-introduced sister products -- the Handheld PC and Palm PC platforms, now dead and transformed into Windows Mobile, respectively -- Microsoft's Auto PC initiative was promised to herald a revolution for in-car entertainment and productivity. There's no question it was well ahead of its time; in fact, many of the features debuted in Auto PC have gone on to become standard fare in today's cars. Problem was, when it launched your ride was already pimped with a mere CD player. In-car navigation, voice recognition, and MP3 support were still the stuff of science fiction in those dark days (particularly at the four-digit asking price), and the whole thing was doomed to a geeky, spendy niche. Though products were initially expected from several manufacturers, Clarion ended up being the only one to actually produce a head unit.

*The Auto PC lived on in spirit as Clarion's Joyride, but Microsoft's heart was no longer in the project and Clarion had switched to a generic Windows CE-based core to build the product.

Microsoft Bob
Introduced 1995, discontinued 1996

Poor Bob. No one ever gave him a chance. Maybe it had to do with the fact that he was really annoying. And as it turns out, Bill was dating Melinda French, Bob's program manager. Which isn't to say there was any nepotism involved -- Bob suffered an early death in 1996 due to general hatred for the little bastard. Bill offered this to a column in January, 1997, "Unfortunately, [Bob] demanded more performance than typical computer hardware could deliver at the time and there wasn't an adequately large market. Bob died." Thankfully, Billinda's blossoming relationship lived on. Oh, did you hear? They're like the world's greatest philanthropists now.

Introduced 1991 (but never released)

Ask folks to pick one word to describe Microsoft's technology roadmap in the 1990s and you'll commonly get "Cairo" in response. Announced before Windows NT 3.1 was even released, Cairo was occasionally an operating system, occasionally a collection of new technologies -- it depended entirely upon who and when you asked -- but at its core, it was intended to guide Microsoft on the path beyond the architecture introduced by NT. After throwing countless dollars and man-hours at the ambitious project, Cairo was ultimately canned (though mentions of the storied buzzword continued even into this decade). Although Windows 2000 eventually became NT's heir apparent, the fruits of Microsoft's labor weren't entirely for naught, as various Cairo features found themselves implanted into various versions of Windows throughout the years. Even the WinFS file system can trace its roots back to the project -- fitting, because it too has become such an albatross.

MSN Music and URGE

Introduced 2004 and 2006, both fully discontinued 2008

When MSN Music -- Microsoft's effort to build its own PlaysForSure-based subscription music based store -- imploded, headstrong Bill did what he usually does: rebrand, and launch again. When he got up at CES 2006 and announced MSN Music would become URGE with MTV, we were all a little skeptical -- after all, the problem wasn't really the service, it was the overbearing DRM and the fact that consumers simply weren't ready for subscription music. Of course, eventually URGE died as well, and MTV shunted customers to Rhapsody America; naturally, Microsoft had a third PlaysForSure-based store waiting in the wings with Zune, which doesn't appear to be going anywhere any time soon.

Origami / UMPC
Introduced 2006
Note: Intel, please join Microsoft on stage to accept this award

UMPCs... what can we say? Sure, Scoble liked them, but even from day one we never saw the market potential. Fueled by an early and too-successful hype-generating viral campaign of Microsoft's own making, there was no way that these first generation Origami devices would achieve their promise. Overpriced, underpowered, desktop OS-laden (with Microsoft's Touch Pack add-on), and poor battery life all helped ensure drown UMPCs in the wave of "ultramobile lifestyle PC"-hysteria they rode to market. And as UMPCs begin to fade, the shrinking niche between smartphones and laptops can look forward to the sweet release of MIDs -- though that's already been two years... and counting.

Dates: introduced 1987, discontinued 2006

What began as a collaboration between Microsoft and then-partner IBM blossomed into what looked like -- for a time at least -- the logical successor to the DOS / Windows empire. The advanced OS showed early signs of greatness with it's incorporation of the HPFS file system, improved networking capabilities, and a sophisticated UI. But cracks in the relationship between the two powerhouse corporations would ultimately lead to its downfall. With Windows 3 a sudden success, IBM's reluctance to go hardware neutral, and Microsoft's increasing displeasure with code which it called "bloated" (ahem!), the project was eventually swept aside by Gates and the gang to make way for what would become the omnipresent operating system you know and love and/or hate today.

SPOT watches and MSN Direct
Introduced 2004, discontinued 2008

When the concept of an information-enabled watch that automagically received content over unused FM radio subcarriers was first conjured up by Microsoft in the early part of the decade, it seemed like a fabulous idea. So much so, in fact, Bill personally took the project under his wing. But by the time it had launched, it was already doomed by a perfect storm of problems: the devices were uglier than sin and comically oversized, the bizarre ad campaign featured frighteningly hairy cartoon arms, and -- as the mobile web was just starting to pick up steam at that time -- virtually anyone who would've been interested in that kind of product had already discovered ways to get the same information from their phone. The underlying data network Microsoft built out to support the watches, MSN Direct, lives on to this day and sees plenty of use in Garmin's nüvi line, but will it ever be used to beam weather, news, and MSFT stock reports to wrists other than Bill's? Not bloody likely.

Windows Activation
Introduced 2001

Depending on who you talk to, Windows Product Activation is a serious privacy violation, a headache, minimal protection against piracy, or all of the above. Lucky for us, Microsoft is finally seeing (some of) the folly of its overbearing ways, and has gone with a more permissive nagware method with Vista SP1. This as opposed to the regular method of routinely locking users out of their systems, which, wouldn't you know it, tended to hurt legitimate users more than pirates. Perhaps the best example of Windows Activation's legacy was the great WGA outage of 2007, which left 12,000 systems out in the cold due to a few downed servers at Microsoft. It didn't take long for the servers to bounce back, but any shred of reputation the service had at that point went out the window with the uptime.

Windows ME
Introduced September 2000

It's not exactly clear what the point of Windows Millennium Edition was -- our guess is that Microsoft needed to keep up with that year-based product naming scheme it had going at the time, and cranked out this half-baked update to '98 in order to capitalize on the turn-of-the-millenium frenzy. Unlike the NT-based Windows 2000 released at the same time, Windows ME retained its MS-DOS-based core, while managing to somehow get even more slow and unstable than its predecessors 95 and 98. And to add insult to injury, it restricted access to shell mode, rendering many MS-DOS apps incompatible. Thankfully, Windows ME was only inflicted upon consumers for little over a year; it was replaced by indomitable Windows XP in 2001.

Windows Vista
Introduced 2007

Vista doesn't suck. Let's just get that off our chests. In fact, it's a quite capable, secure and sexy OS when you get right down to it. Unfortunately, its problems just loomed too large for many folks to overlook. A multitude of delays and a rapidly diminishing feature list soured people right out of the gate, and once the dust settled people just weren't happy with the minor improvements they were getting in exchange for their hard-earned monies and fairly mandatory RAM upgrades. Mix that in with the standard driver incompatibilities of any Microsoft OS upgrade, and you've got a whole bunch of disgruntled downgraders on your hands -- and plenty of bad press to fill in any remaining gaps. Sadly, improvements to Media Center, aesthetics and even that quirky little sidebar got overlooked in the process. Microsoft's already scrambling to get Windows 7 together to capture the multitude of users that've decided to skip Vista altogether, let's just hope it's not too late.

Runners-up: Actimates, Pocket IE, Games for Windows - Live, Xenix (yeah, Microsoft actually did a Unix at one time!)