Next month, Microsoft will be turning 50, and that’s made me wax nostalgic over the various Microsoft games that have come out leading up to this semicentennial celebration (you don’t use that word every day).
During the last half-century, Microsoft has played a historical role not only in tech but within the more niche world of video game software.
I’ve taken time to list the top seven classic Microsoft games from the pre-Xbox era that have had the most impact. So, this won’t include any games technically published by Xbox Game Studios, only titles published under Microsoft or Microsoft Games.
Let’s see if you recognize all seven and let me know in the comments if you agree with my ranking.
7) Microsoft Adventure (1979)
While I don’t have any personal experience with Microsoft Adventure, seeing as how this game was released 11 years before I was even born, it’s undeniably notable since it was the very first game Microsoft ever published, even if it was an adaptation of Colossal Cave Adventure from 1976.
The basic premise is that you are exploring caves and can earn points after successfully solving puzzles and collecting treasures.
In early video game fashion, Microsoft Adventure is a text-based experience, sans graphics, where players read about their environments and then can type in word commands like “South” or “Get rock” in order to travel to different places or interact with in-game objects.
It might not be as popularly played as it once was, but Microsoft Adventure was an important stepping stone that would pave the way for Microsoft to publish additional titles.
6) Microsoft 3D Pinball: Space Cadet (1995)
Included with Windows 95, an audience of people in the 90s and 2000s had instant access to it.
I’m not entirely sure when I first became aware of Microsoft 3D Pinball: Space Cadet (also called Microsoft Pinball), but it would eventually become one of the most revisited games on my ’90s cream-yellow computer.
The premise is the same as with most pinball games — pull back the spring-loaded launcher to set the ball in motion, and then try to hit the metallic sphere up into the scoring areas using the flippers. It’s one of those games that just about everyone who grew up in the 90s with a Windows PC has played, even if they don’t talk about it.
My older brothers would compete to get the highest points and laud their short-term victories over each other until the other took first place. Being age seven in 1995, I never tried to improve or beat my scores. I was simply entranced by the impressive 3D graphics, reactive sci-fi noises, and flashing lights.
Unfortunately, while this beloved Pinball game came with both Windows 95 and 98, it was not included in 64-bit versions of Windows XP (2001). Rumors made it sound like the game was removed for legal reasons.
However, an official Microsoft blog post written by Raymond Chen explains that the tough decision to exclude it was due to a bug encountered on the 64-bit build that couldn’t be rectified by the Microsoft team.
At any rate, it was a sad thing for many when the game didn’t come with later versions of Windows.
5) Crimson Skies (2000)
This tabletop-turned-video game was created by Jordan Weisman and Dave McCoy, developed by Zipper Interactive, and published by Microsoft.
The story is set in an alternate reality 1930s, where flight is the main mode of travel in Northern America, and pirates roam the skies.
After successfully completing a mission and gathering treasures, the main character, Nathan Zachary, discovers that his pirate gang, the Fortune Hunters, has all gone missing.
The story revolves around him undertaking various missions and experiencing dogfights, explosions, betrayal, and more while searching for his crewmates.
Adding to the game’s overall tone, Crimson Skies tells its story like a dramatized radio program, which creates a playful, campy style somewhat reminiscent of a comic book.
What helped Crimson Skies stand out was its creator’s desire to make a fun action game rather than a life-like aviation game. So, it was meant to fulfill adventure fantasies rather than have realistic physics.
There hasn’t been a new Crimson Skies video game in over two decades since Crimson Skies: High Road to Revenge was released for Xbox 360 in 2003. That said, this series still holds a place in many people’s hearts and helped show that the experience and not necessarily realism was more important when it came to gaming.
Of course, Xbox Game Studios currently owns the Crimson Skies IP (intellectual property), so there’s a chance Microsoft could revive it sometime down the road. Until then, you can enjoy Crimson Skies: High Road to Revenge on Xbox Game Pass.
4) Microsoft Flight Simulator (1982)
Yep, another aviation game appears on the list.
Before Microsoft got involved, developer Sublogic created the first FS1 Flight Simulator title in 1980, and then Microsoft acquired them in 1982.
Shortly after this acquisition, Microsoft Flight Simulator was released for IBM PC. The main gameplay has players flying a Cessna 182 aircraft over Chicago, Los Angeles, New York City, or Seattle.
Compared to FS1, Microsoft Flight Simulator offered improved graphics and made flights more exciting by offering both night and day, as well as weather changes.
After releasing the game, Microsoft soon found it had success on its hands, with the Chicago Tribune eventually stating that it was “the most popular game ever on a diskette.” The preeminent title ended up selling about 800,000 copies in its first five years.
These games have helped thousands of people live out their fantasies of being pilots from the safety of their homes. The fantasy gets even more realistic with the use of the best flight sticks and controls.
Depending on how you look at it, there have been 16 Microsoft Flight Simulator games to date since Microsoft got involved.
Now, this aviation series has had its ups and downs and even experienced some initial turbulence with the launch of Microsoft Flight Simulator 2024.
However, it’s still largely considered one of the very best flight sim series out there.
3) Microsoft Minesweeper (1990)
Most of us have heard of Minesweeper (a.k.a. Flower Field), but where did it come from?
While being on Windows 95 made it ubiquitous, Minesweeper was originally developed by Curt Johnson in 1992 for IBM’s proprietary OS/2 operating system but was first released in 1990 with the Microsoft Entertainment Pack 1.
Johnson has acknowledged that he borrowed the concept for the game from a different game (but not Mined-Out), which was pretty standard practice at the time (thanks, Eurogamer).
As with Space Cadet, Minesweeper was a game that came on Windows 95 and soon became one of the biggest sources of workplace distraction in the Windows 95, 98, and XP eras.
Or so I’ve been told. I wouldn’t know firsthand, considering I was seven at the time.
Throughout my childhood, I’d end up watching several adults glued to their computer screens while attempting to beat this game. Those deceptively simple boxes can keep your attention for hours.
Depending on the difficulty, players are presented with 8×8, 16×16, or 30×16 rows of blank boxes and need to determine which ones contain mines and which ones are safe to click on.
If a space has a number 2 on it, then it is in contact with two mines either horizontally, vertically, or diagonally. If there’s a 3, then it’s in contact with three mines. So on and so forth.
By gathering clues, players can slowly clear the field by clicking on safe spaces and marking boxes with flags if they believe they hold mines. However, clicking on even one mine ends the game, which only brings you back feeling unsatisfied and wanting to try again.
It’s not quite as iconic as some of the other games that come with Windows, but it’s still a very popular one that many people have sunk time into.
2) Age of Empires II: The Age of Kings (1999)
I could write a novel about Age of Empires (AoE), but I’ll try to keep this brief.
The 90s was the golden era of real-time strategy (RTS) games like Civilization, StarCraft, Command & Conquer, and more. Even with all of this competition, the original AoE was able to make a splash when Microsoft published it in 1997.
A couple of years later, the medieval-focused sequel, Age of Empires II: The Age of Kings, improved on what already made the original game so great while also bringing new features aboard.
As is a common RTS theme, the goal of Ensemble Studios’ game is to build up a civilization and withstand any attacks made by other players (or the computer). Depending on the mode, you can win by being the last civilization standing or completing specific goals.
To say AoE2 was popular is an understatement.
Not only was AoE2 able to sell over two million copies after only three months on the market, but it stayed in the list of top 20 best-selling video games for the next two and a half years. It would go on to get enhanced and re-released in the years to come on various platforms, including modern PCs and Xbox Series X|S (as seen in my review).
Many people say AoE’s focus on real history set it apart from the many fantasy and sci-fi RTS games of the time. I’m sure this was a factor, but it would be remiss not to mention that AoE2 also offered a wide range of features, extremely competitive yet balanced mechanics, and fully fleshed-out single and multiplayer modes that drew players in.
After AoE2’s initial launch, Microsoft went on to release The Conquerors Expansion in 2000, which refreshed the game by bringing four new campaigns and five additional civilizations (Aztecs, Mayans, Spanish, Koreans, and Huns) to AoE2. But that wasn’t the end of AoE2’s expansion packs.
Several years later, in 2015, The African Kingdom’s expansion came to Steam, and then in 2016, we also got the Rise of the Rajas for the Definitive Edition of AoE2.
In the years following AoE2, we also got Age of Mythology, Age of Empires III, Age of Empires IV, a few remakes and ports, and, most recently, Age of Mythology: Retold, which is a step up from being a basic remake. Even after all of these releases, AoE2 is largely considered the best of the group.
With its massive following and Microsoft’s continued support for AoE2 over the years, it’s no wonder AoE2 has become a classic that is “more widely played than ever” in the eSports scene.
Between my childhood and now, I can’t even tell you how many hours I’ve put into AoE2. It was something that I’d play with my friends and brothers religiously during summer vacations, and now it’s something that I still enjoy after a long workday.
Most importantly to my tweenage self, there was a broad array of silly pre-recorded insults that you could taunt other players with while decimating their units or simply stealing their sheep.
“You played two hours to die like this?”
“WOLOLO!”
What more could you want? AoE2 left a lasting impact on a generation, and it’s still going strong.
1) Microsoft Solitaire (1995)
Did you really expect anything else to be at the top of this list?
I honestly wrestled with putting AoE2 at the number one spot, but I’ve put Microsoft Solitaire here instead because it and its later versions are iconic and have been played by just about everyone.
Microsoft Solitaire was initially released on Windows 3.0 in 1990, but the 1995 version that came with Windows 95 is arguably the most iconic.
I don’t think I’m exaggerating when I say that I’m a Nertz (basically multiplayer Solitaire) whiz due to the many hours I spent playing this time-wasting card game growing up.
Microsoft has gone on to include a version of Solitaire on each of its new operating systems, including Windows 11, even if it is tucked in the Microsoft Store now.
In my adult life, I sometimes find myself spending hours playing newer versions of this addictive card game, all so I can repeatedly get the satisfaction of winning and seeing those cards hop around the screen like bouncy bunnies on a green field.
You know the rush I’m talking about.
Going back to the 95 version, everyone in my family had a preferred card design to choose from; I always went with the night castle theme, while one of my brothers chose the robot, another brother chose the clownfish, and my mother chose the beach scene.
I’ve seen coworkers playing it at work, classmates playing instead of taking notes, and individuals playing it on the flights to pass the time. It’s easy to pick up and is more approachable than a competitive game like AoE.
It’s so everyman that it symbolizes slacking off in the workplace, as is evidenced by its use in movies and shows like The Office, Friends, Peep Show, and many more.
This one is a little bit of a stretch, but it still technically counts.
The original Metal Gear Solid game, designed by the legendary Hideo Kojima and published by Konami, was released in 1998 for PlayStation.
It was so popular that it ended up getting remade and ported to various platforms, including Windows.
To bring the adventure stealth game to Windows PC, Microsoft Games stepped in as publisher with Digital Dialect developing.
In case you don’t know, players take on the role of Solid Snake, a gruff military type and former spy who is tasked with infiltrating a nuclear facility to put an end to terrorist schemes.
The series is still going strong, with Metal Gear Solid Delta: Snake Eater launching in August 2025.
So, while the initial creativity and design for the classic game definitely belongs to Kojima and Konami, it was thanks to the efforts of Microsoft Games and Digital Dialect that many people got to play this game on Windows.
Microsoft games helped develop my gaming tastes
Microsoft has had a large impact on my life and the lives of everyone growing up in the last half-decade.
From casual games like Solitaire to more intensive strategic ones like Age of Empires II, the company has even helped shape my gaming preferences.
It all started with Microsoft Adventure, but eventually, the company would publish a popular series with enormous followings.
Of course, there are several game IPs Microsoft hasn’t touched in years, and we can only hope that Xbox Game Studios will revive these someday.
If you disagree with my ranking, post in the comments, and let’s discuss!
