The 50 best things Microsoft has ever made

This week, on April 4th, Microsoft turns 50 years old. The company has gone through sweeping changes over that time — from two guys in New Mexico to more than a quarter-million employees worldwide, from making text-based operating systems to holographic video games — but through the decades, it’s remained a foundation of the tech world.

Microsoft has made a lot of products over its 50 years, ranging from file formats and PC accessories to cloud servers and design languages. A great many were duds — it’s hard to nail everything over five decades — but a lot were memorable, fascinating, or simply excellent products that would go on to be used by billions of people or change the industry in their wake.

For Microsoft’s 50th anniversary, The Verge spent time sorting through all of those products to decide on the 50 best — the ones we loved, the ones that changed the tech world, or at least the ones we couldn’t get out of our heads.

Our general rule was this: everything on the list had to be a consumer product or otherwise something consumers engaged with. (Sorry, Azure.) The specific version we mention also has to have been made or published by Microsoft at the time of its release. (Minecraft is great, but it was an acquisition.)

We ended with a shortlist of more than 200 products to consider. After whittling it down, arguing over the rules, and re-ranking things more than a few times, here’s our take on the best stuff from Microsoft over its first 50 years.

I can probably trace my hatred of modern AI writing assistants to this dreaded paperclip. Clippit (as it was known before Microsoft conceded that “Clippy” was catchier) was the default character option for the Office Assistant feature that was introduced in Office 97. What was supposed to be a cute guide to help new users get to grips with software features was actually so widely criticized for being annoying, unhelpful, and intrusive that Microsoft itself eventually mocked the feature. Ben Waldman, the head of development for Office 97, even embedded the acronym “TFC” into Clippy’s source code. The “C” apparently stood for clown, and… well, you can infer the rest.

Nearly three decades later, it’s much easier to look back on Clippy as an icon — and a perplexing precursor of what was to come. — Jess Weatherbed

As the internet made having a home PC even more appealing, Microsoft introduced Bob in 1995 as a less intimidating front end for Windows 3.1, 95, and NT. Application icons appeared as random objects around a virtual cartoonish home. Clicking a pen and paper on a desk would open a word processor, while a clock accessed the calendar. Bob is considered one of Microsoft’s more memorable failures (although Rover, an animated dog assistant it introduced, would later be revived as a search companion for Windows XP). — Andrew Liszewski

If you’ve ever completed a Microsoft certification like the Microsoft Certified Solutions Expert (MCSE), you’ve probably come across Contoso, Fabrikam, Northwind Traders, or Datum Corporation. These are all fictional Microsoft companies that are used in product demos and training materials. Contoso is probably the most widely used, as Microsoft has invented a Contoso bank, hotel, pharmaceuticals company, consulting firm, and many more made-up Contoso businesses. — Tom Warren

47. Metro design language

Microsoft’s Metro design language put a heavy focus on typography and simplified icons, creating a stylish, distinct look that could make any interface feel fresh. Microsoft leaned into Metro with its Zune interface, and the software maker eventually debuted the full Metro interface with Windows Phone 7. The design heavily influenced iOS and Android, and Microsoft later brought the style to Windows 8, Outlook, and the Xbox One dashboard. — Tom Warren

46. Internet Explorer for Mac

Internet Explorer for Mac landed at just the right time, with Microsoft locking in a deal to make it the default browser on Apple’s computers a year before the launch of the iMac. The iMac G3 — the computer that saved Apple — was designed around internet connectivity. And that meant getting online through Internet Explorer. — Jacob Kastrenakes

Microsoft’s brown Zune was one of the coolest-looking gadgets ever released. Yeah, you heard me right. Its edges gave off this greenish glow effect that I’ve never seen replicated in other products. And the Zune Pass, which let you permanently keep a few songs each month along with your all-access subscription, was ahead of its time. The Zune’s onboard software was impressively sleek — especially for Microsoft during that era — and similarly, the Zune HD never got enough appreciation for its terrific industrial design and forward-looking OLED display. — Chris Welch

Why’d Microsoft have to give up on its Surface Headphones after just two tries? Look, I won’t tell you they were ever a strong contender in the sound quality department, but everything else about them was genuinely good. First and foremost, the dial controls were ingenious. You’d rotate one ear cup to adjust volume, and the other controlled the level of active noise cancellation. It seems like such an obvious idea, and more headphone makers need to copy it if we’re never going to get a pair of Surface Headphones 3.

Let’s not talk about the Surface Earbuds, though. Those were an unmitigated disaster. — Chris Welch

43. Jon M. Chu’s “Movement” commercial

Though Microsoft was never known for making super memorable commercials, you could feel the company locking in when it tapped Jon M. Chu to direct its “Movement” spot for the original Surface. It was easy to knock “Movement” for focusing on dancers rather than detailing the Surface’s specs and how much it would cost. But watching the ad now, it’s like looking into another reality where companies want their gadgets to seem fun. — Charles Pulliam-Moore

Before becoming the default font for passionate graphic designers everywhere, Comic Sans aimed to make computers seem less intimidating for younger users. Microsoft designer Vincent Connare created Comic Sans in 1994 to contrast with more formal fonts at the time and was specifically inspired by the lettering styles used in The Dark Knight Returns and Watchmen — two notably violent comic books that aren’t recommended for children. It became recognized as a meme after routinely being used in situations where a more serious typeface would have been more appropriate. Even Google is in on the joke — try typing “Comic Sans” into Search. — Jess Weatherbed

Microsoft found its business model fast: after the success of its first BASIC interpreter in 1975, the company reworked it for PC makers across the industry. The result was an early industrywide reliance on Microsoft to make core PC software — a role it’s gladly served ever since. — Jacob Kastrenakes

Windows Hello lets you sign in to a PC with just your face or fingerprint. It’s a great addition to Windows that just works, to the point where I can’t even remember the last time I signed in to my laptop with a password. — Tom Warren

A version of Word so good, people refused to leave it behind. Word 5.1 for Mac was a legendary release, with a clean interface, stable performance, and all the features a mid-90s writer could ask for. After the disaster of Word 6, some Mac owners refused to upgrade for over a decade. — Jacob Kastrenakes

Microsoft’s range of PowerToys have existed since Windows 95, offering up more customization and flexibility for power users. I loved Tweak UI during the XP days for editing Internet Explorer settings, and FancyZones is a great little window manager if you have multiple monitors or a giant ultrawide one. — Tom Warren

Microsoft’s Courier was a prototype dual-screen tablet that the company had been working on in secret before a video leaked online. The prototype tablet, developed by Xbox creator J Allard, had two seven-inch displays with a flexible hinge to make it feel like you were opening a book.

The leaked concept video had many onlookers pining for a tablet like Courier, but the hardware was powered by a custom version of Windows CE that never saw the light of day. One report suggests that Bill Gates stepped in and killed the Courier project. Microsoft eventually announced a Surface Neo dual-screen tablet years later, but just like Courier, it also never shipped. More than a decade later, foldables have taken up the mantle, but we’re still left dreaming of what a dedicated notebook-style tablet could offer. — Tom Warren

I wish Windows Movie Maker still existed. As a teenager, I used the app to learn the basics of video editing and to quickly create videos to share with friends and family or publish on Facebook and YouTube. It was never as fully featured as Adobe’s Premiere Pro, but it was free and easy to use. Microsoft eventually discontinued Windows Movie Maker in 2017, before acquiring Clipchamp to become its default video editing tool in Windows. — Tom Warren

Developer Chris Pirih writes on his website for SkiFree that he created the game for his “own education and entertainment.” But after a program manager for the Microsoft Entertainment Pack saw him messing with the project at work, it ended up being included with Windows 3.0.

I’d argue SkiFree is less a game than a metaphor for the futility of ambition — no matter how good I got at hitting ramps and dodging trees, I was forever destined to be eaten by a yeti in the end. — Wes Davis

It’s easy to forget that Microsoft Windows was originally a failure, that it was one of the very first pieces of “vaporware,” and that the overlapping windows we all associate with Windows weren’t actually part of Windows at its November 1985 debut. Instead, it shipped as a tiled operating system, with each of its windows automatically resizing to fill the remaining space on your screen — much like the Snap feature that shipped with Windows 8 and beyond to help place apps side-by-side.

Overlapping windows arrived with Windows 2.0, and it wasn’t until Windows 3.0 that the operating system really took off. But in hindsight, we can already see the underpinnings of what the power user OS would become, both good (multitasking!) and bad (memory woes).
Here’s how Bill Gates introduced the OS in its original press materials: “Windows provides unprecedented power to users today and a foundation for hardware and software advancements of the next few years. It is unique software designed for the serious PC user, who places high value on the productivity that a personal computer can bring.” – Sean Hollister

With an interface as bland as a pair of golf pants, Microsoft Golf captured the feeling of hitting the links for an early generation of gamers. There’s still something delightful about its crisp sound effects, crunchy trees, and checkbox-heavy gameplay. — Jacob Kastrenakes

I loved Windows Home Server. As a teenage geek, I used to use different versions of Windows Server to enable easy file sharing, printing, and remote access to my home network, but Windows Home Server made this a lot easier. Microsoft put a lot of effort into simplifying PC backup, file sharing, and remote access with this version of Windows, and although it didn’t last very long, it was an important addition ahead of Microsoft’s push into cloud computing. — Tom Warren

Forza Horizon 5 has a soundtrack that’s so good I included half of it in my wedding playlist. The driving is pretty decent, too. Joking aside, with the variety of activities and distractions, I spent days playing Forza Horizon 5 without ever seeing a checkered flag. Instead I would just blast tunes cruising around Mexico, drinking in the scenery, and plowing through the odd cactus patch. — Alice Jovanée, Polygon

The HoloLens wasn’t commercially successful, but Microsoft’s now-defunct mixed reality goggles (not to be confused with the essentially unrelated Windows Mixed Reality platform) were one of the first consumer-level products to demonstrate the form’s promise and grapple with its limitations. Unlike Google’s anemic Glass headset, they did genuinely impressive stuff — projects like HoloLens Minecraft remain almost untopped for sheer cool factor.

Microsoft valiantly tackled problems that high-end AR still hasn’t cracked: heavy hardware, clunky controls, a small field of view, and the fact that wearers look ridiculous. But it never solved them, and HoloLens was dealt a major blow when project lead Alex Kipman allegedly harassed employees and then stepped down. If spatial computing goes mainstream, we’ll probably look back on the HoloLens as ahead of its time; if it doesn’t, the goggles will be a reminder of what — with a few more technological breakthroughs — could have been. — Adi Robertson

In the early days of PC gaming, nothing felt quite as powerful as piloting a mech or flying a plane with a SideWinder joystick. Sure, the future turned out much simpler, but using WASD is a whole lot less fun. — Jacob Kastrenakes

Almost “deprecated” in 2017 but saved by an “outpouring of support and nostalgia,” MS Paint is still kicking, since 1985, living long enough to be injected with “AI tools” that do way more than the once pixel-y canvas ought to be capable of. Though I never modded any Minecraft textures, or created any work-in-progress graphics for my myriad primitive websites, or did anything remotely useful with it at all, I have definitely created some god damn masterpieces (I think). And that’s what MS Paint is best for. Catharsis. Intent. Squiggles. — Marina Galperina

Microsoft complemented its big and bold Windows XP theme with a default wallpaper named Bliss. The photograph of the rolling hills and blue skies of California was initially a stock photo before Microsoft acquired the rights to it and used it to heavily promote Windows XP. As it was the default photo on millions of Windows XP devices, many have speculated that it’s the most viewed photograph in the world. — Tom Warren

26. Bill Gates as Austin Powers

During the ’90s and early ’00s, Microsoft used to host a variety of silly videos on its internal “winweb” corporate intranet. Among them were many videos of Microsoft co-founder Bill Gates dressed up as Superman or Austin Powers, alongside former Microsoft CEO Steve Ballmer playing along, too. This was an era before internet usage was widespread and the ability to send a video to millions of people at the click of a button was possible, so many of them have made their way to YouTube these days. — Tom Warren

25. Xbox Adaptive Controller

Microsoft’s Xbox Adaptive Controller, a controller designed for people with disabilities, came close to never being released. But teams across Xbox and Surface worked together regardless of budget constraints to make the Xbox Adaptive Controller a reality, delivering one of the most capable pieces of accessible hardware in the gaming world. It has encouraged other companies like Logitech to build accessories for the controller, and Microsoft has even gone on to launch an Xbox Adaptive Joystick, too. — Tom Warren

If Halo put the Xbox on the map, creating the template for console first-person shooters for years to come, Gears of War put the Xbox 360 on the map. A third-person, cover-based system seller that was simultaneously the calling card for Epic’s Unreal Engine 3, Gears of War was the blueprint for a modern AAA blockbuster. Why Gears of War 2 on this list then? Horde Mode fans know what’s up. — Chris Grant, Group Publisher, The Verge and Polygon

23. $150 million investment in Apple

In 1997, Steve Jobs returned to Apple and took charge of a company that was months from bankruptcy and in desperate need of help. He found a surprising ally in Microsoft, which agreed to invest $150 million into Apple at a rock-bottom share price. The agreement saved Apple, helped to keep antitrust regulators off Microsoft’s back, and teed Microsoft up to be a key software maker on the Mac for years to come. — Jacob Kastrenakes

If you had internet access in the late ’90s then it was almost certainly via a dial-up service provided by The Microsoft Network (MSN) or America Online (AOL). Either way, the shrill, eye-watering screeching sounds it made are now incredibly nostalgic for a certain generation of individuals. It may surprise you to know that MSN dial-up is actually still available to this day from $21.95 per month, offering rural regions that have yet to adopt broadband connectivity a (somewhat inconvenient) way to get online. – Jess Weatherbed

21. Surface Book keynote presentation

Microsoft has never had the swagger of Apple, never quite been able to blow away a keynote crowd like its competitor could. But at one very memorable presentation in 2015, Microsoft’s then-hardware leader Panos Panay and the Surface team managed to do it. Panay ran through a seemingly complete introduction of the new Surface Book laptop, even announcing a price and release date. And then, when he should have wrapped up, he doubled back and reintroduced the product, revealing that it was actually a tablet capable of splitting in two. The product line would only last for three generations, but it was a compelling-enough idea with solid-enough execution that we still wish Microsoft would bring it back. — Jacob Kastrenakes

Every company starts somewhere, and this is the start for Microsoft: a BASIC interpreter for the Altair 8800 that was so good, it led to a whole line of BASIC interpreters and the foundation of one of the biggest names in tech. — Jacob Kastrenakes

19. Microsoft Flight Simulator 2024

Microsoft gained the Flight Simulator license from Sublogic in 1982 and, by now, it’s clocking in as one of the longest-running game franchises of all time, all for a very specific kind of enthusiast. It’s evolved from wireframe graphics to incredibly precise details — down to that tree line at some small airport in Nowhere, USA — while consistently outpacing other flight sims. The latest 2024 release features changing seasons (and, subsequently, physics), wildfires, and tornadoes to better reflect that real life you’re trying to escape while pretending to fly a plane. – Marina Galperina

Microsoft made sweeping interface changes to Office 2007 that have gone on to influence more than a decade of Office and Windows releases. The biggest and most controversial change was the addition of the Ribbon interface, a section of tabs that houses all of Office’s features. Paint, File Explorer, and many other parts of Windows still use variants of the Ribbon UI. Office 2007 also introduced the Office Open XML format that is still used by cloud-powered Office apps today. – Tom Warren

Launched for the Xbox 360 in 2010, the Kinect was like the cool, older sibling to the Nintendo Wii. You didn’t need any sort of controller for the device to pick you up — you were the controller. It was truly unlike any other gaming accessory at the time, as it used just a camera to capture your full range of motion, spurring delightful games like Child of Eden, Dance Central, and The Gunstringer. — Emma Roth

16. Steve Ballmer’s “Developers!” chant

“Developers developers developers developers developers developers. Developers developers developers developers developers developers developers developers. Yes!” — Jay Peters

One of the all-time great “Wait, Microsoft had a hand in that’s?” Slate was launched by Microsoft to “bring thought-provoking, high-caliber journalism to the Internet’s World Wide Web,” the company wrote on its 1996 launch day. By the time Microsoft sold Slate in 2004, the publication had long since established itself — and helped to establish the web at large — as a space for both entertaining and thought-provoking original writing and as a launching pad for a generation of up-and-coming writers. — Jacob Kastrenakes

Microsoft certainly made a splash when it announced the Xbox Series X at The Game Awards in 2019, and I still think the Xbox Series S looks awesome. But the consoles haven’t proven as popular as the PlayStation 5, and Microsoft now seems to be looking beyond just its own hardware to represent what an Xbox can be. I’ll always have a soft spot for these boxy Xbox Series boxes, though. — Jay Peters

Klondike, who? Windows Solitaire is celebrating its 35th anniversary this May, and it’s the first video game I ever remember “winning.” Really. I could watch those cards spread and bounce across the screen for a very long time. Microsoft intern Wes Cherry originally programmed the game — I guess the lesson here is never underestimate your interns. – Marina Galperina

Microsoft might be ending support for Windows 10 later this year, but a lot of people will still be using the OS for years to come. Windows 10 returned to the traditional desktop interface after Microsoft’s failed attempts at overhauling the UI in Windows 8. Microsoft focused on Cortana integration, Xbox features, and its Universal Windows Platform to let developers build apps that could span across PCs, phones, and Xbox consoles. While Microsoft’s universal app plans never really took off, Windows 10 is widely regarded as one of Microsoft’s best versions of Windows. – Tom Warren

Windows Phone was a glorious failure. It was a bold reimagining of the Windows Mobile interface and platform, thanks to a Start screen interface full of colorful Live Tiles. Microsoft wanted Windows Phone to feel alive, with tiles for apps animating and updating with live information. If you ever used a Windows Phone, your biggest complaint was probably the lack of apps, which doomed Microsoft’s efforts to make a dent in Apple and Google’s mobile dominance. – Tom Warren

Years ago, I was consulted by a worried relative who knew I worked for a tech publication. Their pre-teen son had acquired an email account that ended in “hotmail.com,” and they wanted to know if it was a real email account or some kind of porn service. I assured them that the “hot” was not meant to be lurid but was apparently a reference to the HTML markup language (“HoTMaiL” — get it?) and that the service was indeed legit.

Hotmail, one of the earliest free web-based email services, was developed in 1996 by Sabeer Bhatia and Jack Smith, and it was acquired by Microsoft a year later. It was branded MSN Hotmail, renamed Windows Live Hotmail around 10 years later, became Hotmail again a few years after that, and was finally rolled into Microsoft’s Outlook suite. You can’t get a Hotmail account anymore — but if you have one, you can still use it. Most of the people I know who used to have an account have since moved to Gmail, but I still occasionally come across somebody who stubbornly sticks with their favorite Hotmail address. — Barbara Krasnoff

There was a time not long ago when you had to go to the library and use an encyclopedia if you wanted to learn something new. This was how many-a 90’s kid wrote papers about photosynthesis until Microsoft Encarta came along. It was released in 1993, but I have core memories of the Encarta ’95 splash screen that must have come bundled with a family PC. It wasn’t long for this world, what with Wikipedia coming on the scene in 2001, but it was a game-changer in more than one way.

I’m sure I learned plenty of stuff about mitochondria from Encarta that I failed to retain, but I have absolutely not forgotten its included game: MindMaze. In it, you had to answer trivia questions as you clicked through different rooms of a medieval castle for reasons that never quite made sense. There was a court jester? And matches you could use to illuminate the castle map for a few seconds at a time? It was barely a game at all, if I’m being honest, and I doubt it helped me learn anything new. But playing a game that came with your CD-ROM encyclopedia was a particular kind of thrill that had plenty of staying power — much more than Microsoft Encarta itself.

8. Microsoft Ergonomic Keyboard

I’m not a “keyboard person” like many of my colleagues at The Verge. I like to keep it simple and comfortable. That’s why I keep Microsoft’s ergonomic keyboard on my desk every year. It did the job and was a pleasure to clack on for hours on end. But a couple years ago, Microsoft decided to exit the peripherals market altogether. Incase made a deal with the company to release some of Microsoft’s last designs. I can’t vouch for the quality of those models, but Logitech’s Ergo K860 has slotted in nicely as a substitute so far. Still, the Ergonomic Keyboard’s demise will eventually be what pushes me into a mechanical keyboard habit. — Chris Welch

Before Windows, there was MS-DOS, the simple, text-based operating system that powered computers from IBM and other manufacturers in the 1980s and continued to underpin the earliest versions of Windows. In 2014, the Computer History Museum dubbed MS-DOS, “the bedrock upon which thousands of application programs running on millions of IBM PCs and PC clones depended.” — Jacob Kastrenakes

Microsoft deserves more credit than it gets for innovations it brought to the humble computer mouse. When the original IntelliMouse debuted in 1996, it was one of the first to have a scroll wheel. Three years later, the IntelliMouse Explorer made mousepads obsolete by trading a rolling ball for an optical sensor offering improved accuracy and reliability, and it introduced additional reprogrammable buttons. It was so popular that Microsoft revived the Explorer version in 2017 with a model that worked on glass surfaces but still retained the USB cable. — Andrew Liszewski

Windows XP was so popular that some ATMs are still using it to this very day. Microsoft overhauled the UI of Windows XP with a new green and blue theme named Luna, which many at the time described as Fisher Price-like due to the colorful changes to the start menu and taskbar. There was even a media center edition of Windows XP that was designed for home theater PCs, a special tablet edition for Bill Gates’ dream of tablet computing, and an x64 edition to usher in the era of 64-bit computing. — Tom Warren

The Xbox 360 was Microsoft’s most important Xbox console, cementing the company as a serious competitor to Sony and Nintendo. It had faceplates for customization, different hard drive sizes that you could remove, and plenty of models to choose from. Despite the red ring of death problems, the Xbox 360 was a top seller in the US and turned titles like Call of Duty 2, Gears of War, and Halo 3 into hits that sold millions. — Tom Warren

The Surface Pro started off as an intriguing combination of laptop and tablet, but it took a few attempts until the Surface Pro 3 nailed the formula. The bigger, thinner, and faster Surface Pro 3 was designed to replace your laptop, and the success of Microsoft’s unique design has heavily influenced laptops and tablets over the past decade. — Tom Warren

On November 15th, 2001, Halo: Combat Evolved changed gaming forever. It was the killer app for Microsoft’s first Xbox game console, putting Microsoft on the game industry map. It launched one of the best-selling video game franchises of all time and arguably rebooted the first-person shooter gaming genre.

Before Halo, games like Half-Life gave players a finite amount of health, encouraging them to cautiously poke around corners. Halo broke the mold, giving players a regenerating shield so they could charge into battle like a supersoldier and then retreat before taking permanent harm. And yet, the game’s AI put up a fight anyhow, with the Covenant Elites among the most intelligent foes that gamers had ever seen: dodging your assaults, taking cover, and retreating, only to charge back in with devastating melee attacks.

When Halo 2 arrived three years later, anticipation was so high that many stores held launch parties, almost unheard of at the time, including a notable one in New York City’s Times Square. That game became the killer app for Microsoft’s Xbox Live multiplayer gaming service, which itself went on to become one of Microsoft’s biggest competitive advantages for the Xbox 360.

It’s funny to think Halo came close to becoming a Mac game instead of an Xbox one, though. Steve Jobs personally introduced the game at Macworld 1999. — Sean Hollister

30 years ago, Microsoft was putting the finishing touches on one of its most important operating systems of all time. Windows 95 introduced the start button, taskbar, and notification area, and it even made the leap to 32-bit computing alongside all of its GUI improvements.

Windows 95 set the stage for many parts of Windows that we still use today, including the familiar desktop, File Explorer, My Documents area, and Recycle Bin. Windows 95 also included important changes like the Device Manager and plug and play system to make it easier to install device drivers and connect up peripherals.

There were so many changes to Windows 95 that Microsoft held a public preview program to test out the operating system ahead of its release, under its Chicago codename. Testers paid $20 for access to the beta, which was delivered on 3.5-inch floppy disks.

Windows 95 was so highly anticipated around the time of its release in 1995 that people were even lining up outside stores to buy a copy of the OS. Microsoft spent $1 billion on the marketing campaign for Windows 95, including a commercial featuring the Rolling Stones’ song “Start Me Up” to highlight the new start button in the OS. Microsoft sold a million copies in just four days, setting the stage for three more decades of Windows’ dominance on the desktop. — Tom Warren