The Chessmaster 2000 (1986)
It was a big deal when The Chessmaster first released. This game marked a leap forward in chess video games and would be ported to most mainstream home computers of the time. As such it was widely available and soon became a staple for nerds who liked both chess and early computer tech.
Its AI was refined for the time. It would wipe the floor with any rookie, defending its pieces dutifully while seizing on strong opportunities. It could also surrender in the case of an unwinnable match, though I am not skilled enough to make that happen. Though the AI is an unrelenting foe, Chessmaster did come with a manual that provides an elaborate introduction to chess and its rules. Even providing instructions on how to get better at the game. You can also have the game play back classic matches from across chess history, so that you might learn from the greats themselves.
What hasn't aged so well is the game's own response times. It frequently needs up to half a minute to figure out its next move, slowing gameplay down significantly. This also cuts into the appeal of having a digital version of chess to begin with. If a computer needs more time to think than a real player would, then you'd probably just want to play a real game of chess instead. Right?
The Fidelity Chessmaster 2100 (1986)
Adding only a measly 100 to the game's title undersells the major improvements that The Fidelity Chessmaster 2100 brings to the table. It's everything the first game was, now with upgraded visuals and a far more accessible interface. Content like the classic matches, once hidden away behind complex commands, can now be effortlessly loaded and replayed with normal buttons.
Fidelity also makes major strides in teaching people chess to begin with. Instead of tucking away 20 pages of chess history in a manual, there is now a comprehensive in-game tutorial. You can learn about the rules, what each piece does, and how to perform the more complex strategies. During actual play you can also request tips or undo a move you regret.
The Chessmaster 3000 (1991)
Building on the solid foundation of 2100, Chessmaster 3000 is an another all-around upgrade. Its most prominent improvements are cosmetic. Besides the usual 2d, 3d, or war room views, players can now choose between a variety of board designs and chess sets. This includes fancy options like giving the game a fantasy look. 3000 also introduces sound-effects, though these can get quite repetitive.
That is not to say that gameplay has languished. With Chessmaster 3000, we finally got full mouse control. God Bless! The AI has also continued to improve, particularly in regards to its responses times. It decides on a move much faster now, while still being as intelligent as it has always been. Chessmaster 3000 also introduces AIs other than the Chessmaster himself. You can pick from a number of personalities which will play entirely different. This also includes weaker options like the Newcomer, who makes a much fairer match for any rookie chess players. Finally this series wasn't restricted to just experienced players anymore.
Also neat is the new tournament mode, though I prefer to play singular matches myself.
The Chessmaster 4000 Turbo (1993)
Chessmaster 4000 brings us to the awkward time period where emulating games becomes particularly difficult. You can't just run the game straight from DOSbox nor will it install on modern operating systems, even if you apply tech wizardry to it. I had to set up a Windows 98 virtual machine and install the game to that. I want you to appreciate just how many hoops I had to jump through for this.
The leap in technology is not immediately apparent in gameplay though. The graphics are crisper and there are even more boards to pick from, but there are trade-offs. The game is once again on the sluggish side, with opponents regularly freezing up for no apparent reason. There is a dedicated button to force them to hurry up and I used it a lot.
4000 does further expand on the customization of the AI. You can now tweak your opponent's behavior and level of skill extensively. This game also marks the introduction of chess puzzles to the series, though your options here remain scarce for now.
The Chessmaster 5000 (1996)
Acting as the series' 10th anniversary, Chessmaster 5000 is a major leap forward. Both in terms of graphical capabilities, as well as the underlying tech and data on which the game is founded.
The core of the game benefits from the all-new engine which was designed for speed and greater graphical fidelity. While there is still a lot of waiting between moves, I now get the feeling that this was artificial rather than technical. If that's the case, I sure wish I could turn it off by now. The game and its interface have also been updated for Windows 95 now, which comes with many added benefits. Menus are a lot faster to control for example and everything has context-sensitive tooltips now.
Chessmaster 5000 is also exceedingly proud of its improved mentoring tools. Tutorials are clearer and more in-depth than ever before. The game now also defaults to the coaching view, which provides you hints on what moves to make and why they will benefit you. 5000 also comes with an exhaustive database of historical chess games and hundreds of guides to study. It's the perfect Chessmaster for newcomers to match the mass-market appeal of Windows 95.
Chessmaster 5500 (1997)
Releasing a year later, Chessmaster 5500 is only a minor upgrade over its predecessor. Basically the same game repackaged, but with additional sound. A synthesized voice can either narrate the whole match or read aloud whatever move was just made. Chessmaster 5500 also tied in with Chessmaster Live. An online service where you could take on real players across the web. While a significant update, it is a shame that they had to make their anniversary game redundant in order to implement it.
Chessmaster 6000 (1998)
Another year, another solid upgrade. Chessmaster 6000 incorporates and builds on the improvements that 5500 brought to the table. There are even more tutorials and the (voice) assistant is even more helpful. It narrates your moves, it explains why certain actions are illegal when you try to make them, and you can even get excellent advice on what moves to make. It's honestly quite impressive at how well Chessmaster 6000 can interpret the context of your matches and provide tailored hints. No matter how non-standard of a position you worked yourself into.
Also neat in this edition are 14 recorded matches narrated by international master Joshua Waitzkin. Just watching a classic match play out was always a neat feature of the Chessmaster games, but it's a lot more educational AND fun thanks to Joshua's explanations and tangents.
Chessmaster 7000 (1999)
This is actually the version of the game that I owned back in the day. I could not have asked for a better introduction to chess.
Chessmaster 7000 overhauls the UI entirely. Instead of tucking away everything in drop-down menus, this game actually boots up to a home menu. You can go to the Game Room for a game of chess, a library for reference books or classic games, a database for game records, or the Classroom for tutorials, exercises, and Joshua's narrated games. Entirely new is the Kids Room, which features more accessible learning tools for younger players. Here you can also find some of Joshua's narrated matches, but besides the tactical explanations he also hosts lessons on sportsmanship here. A valuable addition indeed.
Besides accessibility and UI, 7000 maintains the series' high standard for AI. The computer responds to your moves very quickly, so you're never left waiting like in the olden days. Combined with the personalities and other difficulty settings, you have all the freedom to set up games exactly to your liking.
Chessmaster 7000 is also the first game in the series that will run decently well on modern PCs running Windows 11. It's unstable and you're probably better off emulating it, but you can run it natively without too much trickery.
Chessmaster 8000 (2000)
Entering the new millennium, we got Chessmaster 8000. The first entry in the series to be published by Mattel Interactive shortly before it was swallowed up by Ubisoft. This release doesn't add much new, but has some worthwhile tweaks.
You get more of something that was already good. The graphics are a wee bit sharper, there's even more lessons, an even bigger database, and more opponents. The chess engine has also been updated and is now compatible with xboard, allowing you to import more content into the game. It's an update for the real chess fanatics out there. Casual players, however, would find that it was otherwise the same game with the same interface and features.
Chessmaster 9000 (2002)
Welcome to the future! Chessmaster has now moved into the 3D era. You can now freely zoom in on the board and rotate the camera to your heart's content. Unfortunately, this feature is prone to visual bugs where the game isn't sure what goes on what layer. Resulting in pieces melting together and making it needlessly difficult to grab the correct one. Ironically, this makes it more appealing to play on the 2D sets with a top-down perspective.
Besides that, Chessmaster 9000 is also significant because its the only version of the game that was kept in circulation. For years it was the only game in the series available on GOG, while the rest became Abandonware. It was eventually retired from the store, but you can still download it if you purchased it before.
This also makes it the most stable, "modern" incarnation of the series. It runs smoothly on Windows 11 without crashes or other shenanigans. The engine is super fast and there's once again more of everything. More tutorials, more classes, more boards and artstyles. The game now even lets you track your rating.
If you can put up with only playing in 2D, then this is the best version of the game so far.
Chessmaster 10th Edition (2004)
With the 10th edition came a massive streamlining of the Chessmaster experience. The game again went through a massive overhaul, simplifying its main menu down to the 3 core categories of Play, Learning, and Fun. Matching the shiny new look, a lot of the cosmetic options have been discarded in favor of a cleaner, professional feel for the boards and pieces. It is... a mixed bag.
Sure I am pleased that the 3D features now work properly, but it looks dull now and lacks coherence. "Fun" is what used to be the Kids Corner, but there's nothing. You can learn the basics of chess there, which should be rightfully under the Learn tab. You can play a practice match with more visual aids, but there's also a Practice mode with similar features under Play. That just leaves the chess puzzles, which should rightfully be split off into their own thing. The game is also less responsive. Opponents take longer to make their moves and there is a lag to using the menu.
On a positive side, I do appreciate the continued improvement of the educational features. 10th Edition has a wealth of info available both in databases and learning tools, as well as in dynamic tips. The game can show all legal moves or point out weaknesses to exploit. Even have it alert you when you're about to make a blunder yourself. After each match you then get an analysis of how it went and generate an even more thorough report if you're curious. It's not the best it can be, but if you're serious about wanting to improve at chess then this release has amazing features for that purpose.
Chessmaster Challenge (2005)
The next year, a slimmed-down version of 10th edition was made available as a downloadable title. Chessmaster Challenge only contains the basic chess gameplay and chess puzzles. Learning has been cut down to just your standard tutorials on how chess works, eliminating Joshua's long-standing contributions to the series entirely. Addtional lessons were eventually made available as a download, but now narrated by Yasser Seirawan instead.
It's not much, but if you just want to play chess without too much fluff, then Chessmaster Challenge is certainly an option. The core gameplay is perfectly fine.
Chessmaster: The Art of Learning (2007)
The final mainline release in the esteemed Chessmaster series. 21 years of chess gaming history. Capped off by the Raving Rabbids.
In all seriousness, ChessMaster: The Art of Learning—also known as Chessmaster 11 or Chessmaster: Grandmaster Edition—was a fine game to end the series on. It retains the modernizations of the 3D era, but also marks the return of many beloved features from older titles. Joshua and his tutorials are back, as are many of the (silly) customization options that got scrapped in 10th edition.
After years of innovation, it's almost staggering how rich in features Chessmaster has become. It lets you toggle all manner of menus and graphs to customize your experience. You can tweak the chess engine on the fly or set up a custom personality for your opponent. There are mentors, alerts, and other educational features that will help you improve as a player. Chess puzzles are back and there are all-new minigames for the youngest players. Whatever you may need, this game has you covered. And if you just want to play chess without any hassle, then that's fine too. Setting up a new game is fast and the default interface is relatively clean.
It is unfortunately Abandonware. Ubisoft (needlessly) pulled the game from store shelves and the online mode is no longer available. The 3D animated boards are also a tad unstable on modern systems, though it otherwise runs smooth.
Older versions of Chessmaster have a lot to offer, no doubt. If you want the best possible chess experience though, then there's no denying that The Art of Learning is a tough act to beat.
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