A number of great historical moments took place in 1975. South Vietnam fell, Muhammad Ali defeated Joe Frazier in the 'Thrilla in Manila' world championship boxing match, One Flew Over the Cuckoo's Nest swept the boards at the Oscars, and Glenn Campbell's 'Rhinestone Cowboy' topped the music charts.

And Harvard dropout Bill Gates and his high school friend Paul Allen set up a tiny business to write software for a new microcomputer called the Altair 8800.

Their first product is the Altair BASIC language. At some point during that year, the company is called Micro-soft, and then MicroSoft, before it is ultimately named Microsoft.

From those modest beginnings, that company went on to help give birth to an entire industry, change the way we live and work, and become one of the largest software companies on the planet, creating countless millionaires - and several billionaires - along the way.

As Microsoft celebrates its 35th anniversary, I've decided to take an idiosyncratic and opinionated look at the best, worst and most notable moments, technologies, products, decisions and people in the company's history.

So step into our time machine and read on.

Savviest business deal

In November 1980, Microsoft signed an agreement with IBM to provide an operating system for the still-secret IBM Personal Computer, to be released in 1981.

The operating system would ultimately be called PC-DOS, a rebranding of Microsoft's MS-DOS.

Microsoft didn't actually write MS-DOS; instead it paid to have Seattle Computer rewrite its own QDOS (Quick-and-Dirty Operating System) for the purpose, without telling Seattle Computer to whom the operating system would be sold.

(Microsoft signed the contract with Seattle Computer one day after signing the contract with IBM.)

QDOS was largely based on the CP/M operating system, owned by Digital Research.

Ironically, IBM had originally turned to Digital Research for an operating system for the IBM PC, but the two companies' negotiations broke down.

Too bad for Digital Research. Microsoft went on to use its relationship with IBM as a springboard to develop its worldwide dominance in business operating systems.

Smartest acquisition

In July 1987, Microsoft bought Forethought for $14m in cash. Forethought had developed a presentation program for the Macintosh, initially called Presenter, which it renamed PowerPoint for trademark reasons.

PowerPoint later became one of the core programs of Microsoft Office, which for many years has been the dominant office productivity suite.

Prickliest partnership

In August 1985, Microsoft and IBM signed a deal to partner in the development of an advanced operating system called OS/2.

The operating system never achieved the widespread popularity of DOS - or, later on, Windows - and became a bone of contention between Microsoft and IBM.

Microsoft devoted most of its development resources to Windows and Windows NT, rather than OS/2, and ultimately abandoned OS/2 to IBM, which eventually abandoned it as well.

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  1. We look at the company's best, worst and most notable moments
  2. Most surprising investment
  3. Most reviled OS
  4. Biggest under-the-radar success
  5. Worst server glitch
  6. Best productivity booster
  7. Splashiest product launch
  8. Smartest market targeting
  9. Weirdest company spokesperson
  10. Most favourable court decision
  11. Best use of company billions


We take an opinionated look back at the good, the bad and the ugly of Microsoft's 35-year history

Most surprising investment

In August 1997, long-time Microsoft rival Apple was teetering on the brink of disaster and in desperate need of cash.

Microsoft rode to the rescue, buying $150m in nonvoting Apple stock.

As part of the deal, Microsoft agreed to continue to develop Microsoft Office for the Mac, and Apple agreed to bundle Internet Explorer with the Mac OS operating system as the default browser.

Both parts of the agreement have since fallen by the wayside: IE for the Mac is gone, and although Microsoft continues to update Office for the Mac (usually some time after the Windows version is updated), it isn't required to do so.

Most prophetic memo

In February 1976, Gates issued a public letter berating people who were freely distributing tapes of the version of BASIC he and Paul Allen wrote for the Altair, without paying Microsoft for them.

Here are excerpts from Gates' 'An Open Letter to Hobbyists', sent to the Homebrew Computer Club:

"The amount of royalties we have received from sales to hobbyists makes the time spent of Altair BASIC worth less than $2 an hour.

"As the majority of hobbyists must be aware, most of you steal your software.... Who cares if the people who work on it get paid?

"Who can afford to do professional work for nothing? What hobbyist can put three man-years into programming, finding all bugs, documenting his product and distribute for free?"

Although the term open source hadn't been coined at the time, this letter set the stage for Gates' career-long battle with open-source and free software advocates.

Most beloved OS

Two operating systems stand out in Microsoft's long history as having more than their share of fans: MS-DOS 5 and Windows XP.

Released in 1991, MS-DOS 5 was stable, fixed the worst problems of its notoriously buggy predecessor, MS-DOS 4, and for the first time broke the 640K memory barrier for DOS, allowing memory beyond that to be used for programs, drivers and so-called Terminate and Stay Resident (TSR) programs.

With 2001's Windows XP, Microsoft finally merged its consumer and business lines of Windows, essentially building a consumer-oriented operating system on top of the stable Windows NT kernel.

It also finally stopped using DOS as the base operating system, making Windows XP far more stable and reliable than previous versions of Windows.

Some people believe XP was too much of a success, because Microsoft has had a hard time getting people to give it up for newer Windows versions.

In 2008, more than 200,000 users signed a 'Save XP' petition, run by PC Advisor's sister magazine InfoWorld asking Microsoft to continue support for the aging operating system.

Which is the most beloved? I'll give the nod to Windows XP. MS-DOS 5, as good as it was, ultimately led to a dead end - it was the best operating system in a line that eventually died out.

Windows XP, in contrast, lives on not only on many people's computers, but in the heart of Windows 7, which still retains its predecessor's merged business and consumer lines.

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  1. We look at the company's best, worst and most notable moments
  2. Most surprising investment
  3. Most reviled OS
  4. Biggest under-the-radar success
  5. Worst server glitch
  6. Best productivity booster
  7. Splashiest product launch
  8. Smartest market targeting
  9. Weirdest company spokesperson
  10. Most favourable court decision
  11. Best use of company billions


We take an opinionated look back at the good, the bad and the ugly of Microsoft's 35-year history

Most reviled OS

Here you've got to choose among MS-DOS 4, Windows Me and Windows Vista.

Released in 1988, MS-DOS 4 was notoriously buggy, and many applications refused to run on it. Users commonly reverted to MS-DOS 3.3 or jumped ship to Digital Research's DR-DOS 3.41 to avoid MS-DOS 4, Microsoft's first serious misstep in operating systems.

Windows Me, released in 2000, was buggy as well, and plagued by installation problems and a plethora of hardware and software incompatibilities.

But I give the 'most reviled' crown to 2006's Windows Vista, which proved to be far more of a fiasco than Windows Me or MS-DOS 4.

The five-year gap between the release of XP and Vista was the longest gap between versions of Windows ever, so people had high expectations for Vista. Unfortunately, it was plagued by hardware incompatibilities at launch, it wouldn't run on older hardware, and many people disliked its resource-hungry user interface.

Making matters worse, many PCs that were tagged as 'Vista Capable' couldn't run the full version of the operating system - a situation that led to a class-action lawsuit against Microsoft.

Best follow-up OS

Again we've got a toss-up here, between DOS 5, which fixed DOS 4's many problems, and Windows 7, which cured Vista's. I'll choose Windows 7, which is the OS that many people believe Windows Vista should have been.

It is faster than Vista, does not have the same hardware incompatibilities, dumps some useless applications, and delivers some nice tweaks, including an innovative, much-improved taskbar.

The proof is in the pudding: both businesses and consumers are finally beginning to let go of nine-year-old XP and make the jump to Windows 7.

Furthest-reaching OS

In July 1993, Microsoft launched Windows NT.

Designed for businesses rather than consumers, NT was constructed from the ground up, not built on top of DOS as previous versions of Windows had been.

More stable and more secure than Windows 3.1, NT was the first completely 32-bit version of Windows.

Its first release was called NT 3.1 to match the consumer version of Windows, but it was put on its own development cycle with its own naming conventions, culminating in Windows 2000, which was released in 2000.

Ultimately, the business and consumer lines of Windows were merged in Windows XP, released in 2001, and the NT kernel became the core of XP and all subsequent versions of Windows - which means that except for a scattered few diehards still using the Windows 3.x and 9x lines, all of today's Windows users are using a direct descendant of NT.

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  1. We look at the company's best, worst and most notable moments
  2. Most surprising investment
  3. Most reviled OS
  4. Biggest under-the-radar success
  5. Worst server glitch
  6. Best productivity booster
  7. Splashiest product launch
  8. Smartest market targeting
  9. Weirdest company spokesperson
  10. Most favourable court decision
  11. Best use of company billions


We take an opinionated look back at the good, the bad and the ugly of Microsoft's 35-year history

Biggest under-the-radar success

A lesser-known product success story is Microsoft SQL Server, which has a somewhat ropey history.

It began in 1988 as a joint venture among Microsoft, Sybase and the now defunct Ashton-Tate, and was designed for the troubled OS/2 operating system.

The product was largely a port of Sybase SQL Server 3.0, which ran on a variety of operating systems, including Unix and VMS. Microsoft and Sybase ultimately parted ways, with Microsoft developing SQL Server for Windows NT and Sybase changing the name of its version to Adaptive Server Enterprise.

These days, SQL Server has grown to become the third most popular database software in the world, behind those of Oracle and IBM.

Smartest software bundling

Clearly the smartest software bundling move Microsoft ever made was combining Word, Excel and PowerPoint into Microsoft Office, first for the Mac in 1989 and then for Windows in 1990.

Microsoft Word, which Microsoft originally (internally) called Multi-Tool Word, was released in 1983 for MS-DOS, in 1985 for the Mac and in 1989 for Windows.

Excel was launched in 1985 for the Mac and in 1987 for Windows. Also in 1987, Microsoft released PowerPoint for the Mac, essentially a version of an application called Presenter that was created by Forethought, a company Microsoft had purchased that year.

In 1990, PowerPoint for Windows was released.

Excel fun fact

When Excel was first developed, Microsoft already had a spreadsheet called MultiPlan, but it was not selling well on the MS-DOS platform.

The company decided it needed a much better offering to compete against Lotus 1-2-3, the best-selling spreadsheet program at the time.

Thus, Excel was originally code-named 'Odyssey' because it was intended to eat Lotus.

(In Homer's Odyssey, Odysseus' crew members ate the narcotic lotus plant in the Land of the Lotus.)

Microsoft's bundling of Word, Excel and PowerPoint into the Office suite emphasised the company's commitment to business desktop computing.

It proved to be a huge success, ultimately leading to the downfall of onetime market-leading applications Lotus 1-2-3 (spreadsheet), WordPerfect (word processor) and Harvard Graphics (presentation program) - and to a near-monopoly for Microsoft Office in the business world.

Sneakiest software bundling

I'll give the award for sneakiest software bundling, hands-down, to Windows Genuine Advantage (WGA), Microsoft's antipiracy software.

WGA warns people when they do not have a paid-for and registered version of Windows, and certain updates can't be installed unless WGA is installed and has verified that the copy of Windows is genuine.

In mid-2006, Microsoft began sending WGA to users' computers along with security updates via Windows Update; the company even labelled the WGA download as ‘high-priority'.

Unbeknownst to users, though, the update had nothing to do with security or stability - it was WGA, sneaking onto their hard disks.

Scot Finnie from Computerworld, PC Advisor's sister magazine, wrote in July 2006: "Microsoft is preying upon people's ignorance - and their strong desire to install security updates. It's clearly wrong for Microsoft to use its security updating channel to install software that has no security benefit, and no benefit at all to its customers".

Users were frustrated enough that a lawsuit was filed, although the suit was recently dismissed.

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  1. We look at the company's best, worst and most notable moments 
  2. Most surprising investment
  3. Most reviled OS
  4. Biggest under-the-radar success
  5. Worst server glitch
  6. Best productivity booster
  7. Splashiest product launch
  8. Smartest market targeting
  9. Weirdest company spokesperson
  10. Most favourable court decision
  11. Best use of company billions


We take an opinionated look back at the good, the bad and the ugly of Microsoft's 35-year history

Worst server glitch

As if users weren't annoyed enough about Windows Genuine Advantage, from August 24 to 25, 2007, the antipiracy validation system accused thousands of paying Windows XP and Vista customers of being software pirates.

According to Microsoft, the WGA servers went on the fritz, and users were tagged as running non-genuine versions of Windows.

Even worse, Vista systems were stripped of important features, such as the Aero interface. The meltdown lasted for 19 hours.

Most embarrassing product glitch

When you use formulas in Excel, you expect them to do the maths correctly - after all, what is a spreadsheet for?

But in September 2007, an Excel 2007 bug had Microsoft execs red-faced with embarrassment because of an apparent inability to do simple multiplication.

In some specific cases, if a formula resulted in the number 65,535 or 65,536, Excel would instead display the result 100,000.

The problem, according to Microsoft, was not that Excel failed maths; it was a display issue. Excel actually performed and stored the calculation properly, the company claimed, but displayed the wrong results.

Microsoft fixed the bug, and Excel has known its multiplication tables - and how to display them - ever since.

Smallest annual revenue

In 1975, its first year in business, Microsoft recorded a total income of $16,005, all from the BASIC program it wrote for the MITS Altair 8800 computer.

The total did not include $14,405 that Microsoft was still owed for the final quarter of 1975.

Largest annual revenue

In its 2008 fiscal year, Microsoft raked in $60.42bn in revenue, a whopping 18 percent increase over what it had earned the previous year.

Worst year-over-year performance

Microsoft has turned a profit every year since its founding, and it enjoyed year-over-year increases in revenue and profits every year ... until 2009.

For its 2009 fiscal year, which ended June 30, 2009, the company reported revenue of $58.44bn, a 3 percent decline from fiscal year 2008.

Its operating income was $20.36bn, down 9 percent from 2008; net income was $14.57bn, down 18 percent; and earnings per share was $1.62, down 13 percent.

Most annoying productivity tool

In November 1996, Microsoft launched Office 97, which featured the Office Assistant, an animated character in the form of a paper clip nicknamed Clippy.

(There were other characters as well, but Clippy was the default and the most annoying.)

The Office Assistant was supposed to help people get work done more easily by popping onto the screen and offering tips from the application's Help system related to the task being performed.

It was intrusive, intensely annoying and widely reviled.

Even people within Microsoft hated Clippy. Steven Sinofsky, now president of the Windows and Windows Live Division, wrote this in his blog: "The Office Assistant was famously named TFC during development. The 'C' stood for clown. I will let your active imagination figure out what the TF stood for".

In fact, Microsoft used the widespread hatred of Clippy to its advantage by launching an anti-Clippy website as a way to promote Office 97's successor, Office XP, because Office XP had the Office Assistant turned off by default.

The site received some 22 million page views, according to USA Today, and allowed users to do things such as shoot rubber bands at the hated animated character.

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  2. Most suprpising investment
  3. Most reviled OS
  4. Biggest under-the-radar success
  5. Worst server glitch
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  7. Splashiest product launch
  8. Smartest market targeting
  9. Weirdest company spokesperson
  10. Most favourable court decision
  11. Best use of company billions


We take an opinionated look back at the good, the bad and the ugly of Microsoft's 35-year history

Best productivity booster

In March 2006, Microsoft released Office 2007, which featured a brand new interface.

Gone were the familiar menus and toolbars, replaced by the Ribbon, which put the most commonly used commands on a series of tabbed panels.

Although some people hate the Ribbon, many users find it easier to use than the old interface once they've gotten used to it.

Microsoft claims that research shows that the ribbon is a productivity booster - so much so that the company has decided to incorporate elements of it throughout its entire product line, including the Windows operating system itself.

Most inexplicable advertising campaign

Microsoft has spent untold millions of pounds on advertising through the years, but one campaign stands out above them all for its sheer incomprehensibility - the series of ads in which the odd couple of Bill Gates and Jerry Seinfeld do mundane things such as search for cheap shoes at a bargain basement discount store and annoy a family for no apparent reason.

Launched in September 2008, these ads were widely criticised in the advertising and tech worlds.

They lasted only a brief time; Microsoft was smart enough to can them quickly.

Most effective advertising campaign

Microsoft clearly learned from the Seinfeld ad fiasco, because the company in early 2009 followed that campaign with what may have been its most effective series of ads - the Laptop Hunter commercials.

The ads portrayed attractive, personable young people searching for laptops and buying Windows-based machines because they found them to be more powerful and less expensive than Macs.

The ads hit Apple where it hurt, on price, at a time when the economy was tanking. The image-measuring firm BrandIndex found that the campaign raised Microsoft's ranking of value perception among 18 to 34-year-olds from zero to 46.2 in a few months, while Apple's plummeted from 70 to 12.4 in the same time period. (The highest possible value was 100.)

Most underwhelming product launch

Windows 1.0's release registered as barely a blip on the computing world's radar.

Begun in 1981 and initially dubbed 'Interface Manager', Microsoft's first graphical operating system was announced in 1983 but not released until 1985.

It didn't run as a standalone operating system; instead, users had to launch it from within DOS. And by the time it was released, its thunder was stolen by Apple's Macintosh computer and graphical Mac operating system, which launched in 1984.

Most game-changing product launch

In May 1990, Microsoft brought graphical computing to the masses with the launch of Windows 3.0.

Versions 1 and 2 of Windows were underwhelming, underpowered and largely ignored, except by people who needed a runtime version to operate software that required windows, such as PageMaker. But the third time was the charm.

Although windows-based operating systems were in use elsewhere, notably on the Mac, Windows 3.0 was a revelation for PC users, with a graphical interface, multitasking and copy-and-paste, among other features. Finally, a reason to buy a mouse!

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  1. We look at the company's best, worst and most notable moments 
  2. Most surprising investment
  3. Most reviled OS
  4. Biggest under-the-radar success
  5. Worst server glitch
  6. Best productivity booster
  7. Splashiest product launch
  8. Smartest market targeting
  9. Weirdest company spokesperson
  10. Most favourable court decision
  11. Best use of company billions


We take an opinionated look back at the good, the bad and the ugly of Microsoft's 35-year history

Splashiest product launch

In 1995, Microsoft launched Windows 95, with an advertising campaign that was estimated to have cost $300m and was said at the time to be the biggest in history.

Microsoft is rumoured to have paid $12m just to buy the rights to the Rolling Stones' ‘Start Me Up', which was Windows 95's theme song and inescapable anthem.

In addition to a massive television-radio-and-PR blitz, Microsoft draped a 300-foot Windows 95 banner over Toronto's CN Tower, paid for a print run of 1.5 million copies of The Times and distributed them for free, and had New York's Empire State Building lit up with Microsoft's corporate colours of yellow, red and green.

As David Segal wrote in The Washington Post on August 24, 1995: "You can hide under a bridge, row a boat to the middle of the ocean or wedge yourself under the sofa, cover your ears and then hum loudly. But get near a newspaper, radio, television or computer retailer today and you will experience the multimillion-dollar hype surrounding the launch of Windows 95".

Best and worst browser launch

In September 1997, Internet Explorer 4 launched, cementing Microsoft's browser dominance and ultimately killing Netscape Navigator as a competitor.

With the introduction of IE4, Microsoft also tied Internet Explorer more deeply to Windows.

This came back to haunt the company when it was sued by both the US government and the European Union for anticompetitive behaviour, including using Windows to force people to use Internet Explorer instead of competing browsers.

Worst interface

Go to any list of the worst software ever written, and 1995's Microsoft Bob will be on it.

Designed for Windows 3.1 and later Windows 95, it was supposed to be a user-friendly interface to help non-techies use computers.

Instead, it was so cloyingly cute that, in comparison, photos of big-eyed puppies appear to be deep and meaningful.

Bob was also confusing to navigate; sucked up system resources, reducing computers to a crawl; and was widely derided in the general and tech press. Users stayed away in droves.

Microsoft Bob was overseen for a time by Melinda French, who was Bill Gates' girlfriend at the time and later became his wife.

If you want to see Bob in action yourself, check out this video of Bob (Warning: The video contains extreme stupidity, horrendous interface design and a nonstop stream of intense monotony.)

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  1. We look at the company's best, worst and most notable moments 
  2. Most surprising investment
  3. Most reviled OS
  4. Biggest under-the-radar success
  5. Worst server glitch
  6. Best productivity booster
  7. Splashiest product launch
  8. Smartest market targeting
  9. Weirdest company spokesperson
  10. Most favourable court decision
  11. Best use of company billions


We take an opinionated look back at the good, the bad and the ugly of Microsoft's 35-year history

Smartest market targeting

Microsoft's earliest products were for individual users, rather than for IT departments, but the company knew that ultimately it would have to sell products aimed at enterprises if it wanted to thrive.

On June 11, 1996, the company launched Microsoft Exchange Server, which was originally written to handle Microsoft's internal email.

(Previously the company used a Xenix-based email system.)

Exchange Server was first released as Version 4.0, apparently to continue the numbering convention of the earlier Microsoft Mail product, which was at Version 3.5.

Exchange has since expanded to include other communications functions such as mobile device syncing and email/voice-mail consolidation, and it has become a cornerstone of corporate IT departments.

Best hire

Love him or loathe him, there is no doubt that Steve Ballmer's hard-driving, relentless style and laser focus through the years have helped Microsoft become the world's most successful software company.

Ballmer, who knew Gates from their Harvard days, came to Microsoft in June 1980 as one of the young company's few employees with real-world business experience.

He had worked for Procter & Gamble after graduation and had attended Stanford Business School for one year before joining Microsoft.

Worst waste of visionary talent

Ray Ozzie is one of the technology industry's true visionaries. He worked on the first spreadsheet, VisiCalc, and developed the Lotus Symphony office suite.

And that was only the prelude: he launched Iris Associates, which developed the software that would become Lotus Notes, and later Groove Networks, which developed the collaboration software Groove Virtual Office (now called Microsoft Office Groove).

In April of 2005, Microsoft bought Groove and Ozzie became Microsoft's chief technical officer. In June 2006, he was promoted to chief software architect, a title previously held by Bill Gates.

Many industry watchers had high hopes for Ozzie's influence at Microsoft, but he has done little to change the company's direction, software or culture, particularly when it comes to his specialty, collaboration.

Beyond adding Groove to the Office suite, Microsoft has done little to develop it, sell it or make it central to the company's strategy.

The upcoming version of Office for the web doesn't even have basic synchronisation features, and the 'Live' brand is a mess, consisting of an odd mishmash of downloadable software and web-based services, with no real connection between them.

Why hasn't Ozzie made his mark? Some postulate that there's a dog-eat-dog culture at Microsoft, with too many people protecting too much turf, and he's never managed to adapt.

NEXT PAGE: Weirdest company spokesperson

  1. We look at the company's best, worst and most notable moments 
  2. Most surprising investment
  3. Most reviled OS
  4. Biggest under-the-radar success
  5. Worst server glitch
  6. Best productivity booster
  7. Splashiest product launch
  8. Smartest market targeting
  9. Weirdest company spokesperson
  10. Most favourable court decision
  11. Best use of company billions


We take an opinionated look back at the good, the bad and the ugly of Microsoft's 35-year history

Weirdest company spokesperson

Most companies like their public faces to be sober, measured and thoughtful - but then, most companies don't have Steve Ballmer at the helm.

Although he's been a boon for the company overall, Ballmer has also been prone to public fits of behaviour that at times appear to be just plain strange.

The most well-known of these is the infamous 'Monkey Boy dance' in which, center stage at a conference, Ballmer danced, howled, screamed and generally acted the madman to show his enthusiasm for Microsoft.

Another YouTube favourite is the 'Developers' video, which captured him soaked with sweat, screaming "Developers, developers, developers, developers..." until his voice gave out.

Best company spokesperson

Bill Gates - his geekiness and intelligence eventually won over the press, and he became a near-ubiquitous magazine cover boy before his retirement in June 2008.

Worst PR disaster

In February 2008, extremely embarrassing internal documents were released in what's known as the Vista 'junk PC' lawsuit.

The class-action suit against Microsoft charged that the company misled consumers into buying Windows XP computers that were marked 'Windows Vista Capable' - even though those PCs couldn't run the most important features of the then-new operating system.

Over several months, internal Microsoft documents became part of the suit, including one from an unnamed employee, who wrote in an email: "Even a piece of junk will qualify" to be called Windows Vista-capable.

And in another email message, Mike Nash, who is now a corporate vice president for Windows product strategy, wrote :"I PERSONALLY got burnt.... Are we seeing this from a lot of customers?... I now have a $2,100 email machine".

Jim Allchin, who at the time of the Vista-capable PC push was the co-president of Microsoft's Platforms and Services Division, wrote in an email: "We really botched this.... You guys have to do a better job with our customers".

Later emails revealed that Microsoft may have launched the marketing scheme in order to help Intel sell low-end chips that were not capable of running the full version of Vista.

Most stunning court decision

On April 3, 2000, a US federal court ordered that Microsoft be split up.

As a result of an antitrust suit filed in 1998 by the US Justice Department, Judge Thomas Penfield Jackson ordered that Microsoft be broken up into two companies: one that would develop and sell operating systems, and another that would handle other types of software.

This followed Jackson's November 5, 1999, findings of fact in which he declared Microsoft a monopoly that used its power to attempt to destroy perceived threats from competing companies, including Netscape, Apple, Sun, Lotus and others.

The court's breakup order ultimately did not stand.

NEXT PAGE: Most favourable court decision

  1. We look at the company's best, worst and most notable moments 
  2. Most surprising investment
  3. Most reviled OS
  4. Biggest under-the-radar success
  5. Worst server glitch
  6. Best productivity booster
  7. Splashiest product launch
  8. Smartest market targeting
  9. Weirdest company spokesperson
  10. Most favourable court decision
  11. Best use of company billions


We take an opinionated look back at the good, the bad and the ugly of Microsoft's 35-year history

Most favourable court decision

This one's a toss-up between two very big decisions. First up is a $5.5bn suit filed in 1988 by Apple against Microsoft and HP alleging that Windows violated the ‘look and feel' of the Mac operating system.

Over the years, the lawsuit was whittled down by a variety of courts, and on June 1, 1993, Federal District Judge Vaughn Walker issued a summary judgement against Apple and in Microsoft's favour.

That was certainly a significant decision, but it ultimately would not have affected the way in which Microsoft did business - Microsoft could have simply paid Apple royalties and continued on its merry way.

An even more important decision for Microsoft happened on June 28, 2001, when the DC Circuit Court of Appeals overturned Judge Thomas Penfield Jackson's 2000 order to break up Microsoft.

Despite the overturning of Jackson's ruling, his findings of fact remained intact, and the case against Microsoft continued dragging on through the courts until 2002.

Biggest relief

On November 1, 2002, the Department of Justice and Microsoft settled the antitrust case against Microsoft.

The complex agreement required that Microsoft share its application programming interfaces (API) with other companies and take a variety of other steps to curb anticompetitive behaviour.

However, Microsoft was allowed to stay intact as a single company.

Worst moment in international relations

On February 27, 2008, the European Union slapped a record fine of $1.3bn on Microsoft for anticompetitive behaviour.

The EU levied the fine for violating the terms of an agreement the company had reached with it in 2004 to curb anticompetitive behaviour 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".

Most misleading product demo

At Microsoft's antitrust trial in 1998, the company backed up its claim that Internet Explorer and Windows couldn't be easily separated with a taped product demonstration showing that removing Internet Explorer from Windows caused system instability and slowdowns.

It was shortly revealed, though, that Microsoft's demo was falsified, as was a subsequent one showing that it was easy for America Online users to install Netscape Navigator on their Windows desktops.

NEXT PAGE: Best use of company billions

  1. We look at the company's best, worst and most notable moments 
  2. Most surprising investment
  3. Most reviled OS
  4. Biggest under-the-radar success
  5. Worst server glitch
  6. Best productivity booster
  7. Splashiest product launch
  8. Smartest market targeting
  9. Weirdest company spokesperson
  10. Most favourable court decision
  11. Best use of company billions


We take an opinionated look back at the good, the bad and the ugly of Microsoft's 35-year history

Best use of company billions

Over the years, Microsoft has made billions in profits for itself and its investors, and that money has been spent in many ways.

But clearly Microsoft founder Bill Gates has put that money to its best use through his founding of the Bill & Melinda Gates Foundation.

The foundation, which has an endowment of more than $34bn, has awarded a total of more than $21bn in grants since its founding in 1994, and it paid $2.8bn in grants in 2008 (the most recent year for which figures are available).

The grants focus on global health issues, global development (such as agricultural development), and a variety of issues in the United States, with a primary focus on education.

Worst nightmare

On September 4, 1998, Stanford University students Larry Page and Sergey Brin founded Google.

Since its launch, Google has dominated internet search, a market that Microsoft initially ignored and now must play catch-up in.

Google has also entered the email and productivity software markets with its Gmail and Google Docs offerings, and it has introduced a browser called Google Chrome and an operating system called Chrome OS.

On top of that, it offers a slew of other services and tools - making it Microsoft's biggest threat in coming years.

  1. We look at the company's best, worst and most notable moments 
  2. Most surprising investment
  3. Most reviled OS
  4. Biggest under-the-radar success
  5. Worst server glitch
  6. Best productivity booster
  7. Splashiest product launch
  8. Smartest market targeting
  9. Weirdest company spokesperson
  10. Most favourable court decision
  11. Best use of company billions