The Chessmaster Died in 1997

August 27th, 2012 by Benj Edwards

The ChessmasterThe Chessmaster (1916-1997)

This iconic wizened head loomed large over my childhood. It is the image of the Chessmaster, a fictional chess opponent who stars in a software series of the same name.

That series began way back in 1986 with The Chessmaster 2000, a comprehensive chess simulator that first appeared on 8-bit computer platforms like the Apple II, Atari 800, and Commodore 64. Published by The Software Toolworks, it spawned a series of at least 16 titles that quickly became the best-selling chess software franchise of all time.

Chessmaster 2000 Box ArtMy older brother always loved chess games, so I saw that aged face — a perennial feature of Chessmaster box art — many times throughout the 1980s and 1990s. I always wondered: who was the Chessmaster, really? Who was the real man behind that wise old face? Was he really that old or was he just wearing a wig?

Fast forward to 2006. Thinking I’d write about it on this blog, I emailed Ubisoft (the current publisher of The Chessmaster series) and asked them if they knew who portrayed the Chessmaster. Of course, they had no idea — institutional memory is sorely lacking in most tech companies, and it’s even worse in the software industry. Today I know better than to even bother asking.

Instead of tracking down everyone who worked on Chessmaster 2000 and interrogating them (although I considered it), I figured I’d bide my time and put the somewhat trivial issue on the back burner. The Internet has a way of consuming information and making it available to everyone online, so I thought the answer would pop up one day.

It did.

The Chessmaster Revealed

Will Hare, the ChessmasterWill Hare, the face and hands of the Chessmaster

A few years later, I decided to resume my quest with a quick Google search about the Chessmaster. Sure enough, my patience rewarded me with an answer to my question. There, buried among the links, lay an IMDB biography that revealed the Chessmaster’s true identity.

The man who portrayed the Chessmaster in that iconic photograph was an actor named Will Hare, who appeared in over 50 film and TV roles between 1948 and 1997.

Judging from his IMDB entry, it seems that Hare mostly played minor, supporting roles — although sometimes they were in big movies. For example, he portrayed Old Man Peabody in the 1985 blockbuster film Back to the Future. And he did it not too long before he portrayed the elderly Chessmaster.

Will Hare in Back to the FutureIn fact, Hare really had the “old man” role cornered around that time: the photo above is a still from Silent Night, Deadly Night (1984), where he played “Grandpa.” He also portrayed characters named “Old Man” in Tales of the Unexpected (1984) and The Aviator (1985).

Immediately after discovering the man behind the Chessmaster, I wondered if he was still alive. Could I call him up and ask him what it was like to be a chess symbol?

No, I discovered. Will Hare suffered a heart attack in 1997 while rehearsing a role at The Actor’s Studio in New York. He died on stage at the age of 81.

According to his bio, he would have been about 70 years old at the time of the Chessmaster photo session. So he really was old enough to be the Chessmaster. That might not be a wig.

Unsolved Mysteries

The sudden and unfortunate death of Will Hare 15 years ago leaves many unimportant and non-pressing questions unanswered.

Who took the Chessmaster photo? (Are there any outtakes where he’s playing checkers?) What were his contract terms? How much was he paid? Did he frame a copy of the box art and keep it on his wall? Did he know that his image would live forever in the distinguished hall of haunting computer game memories?

If anyone out there knows the answers to these questions, contact Robert Stack please leave a comment below. Heck, even if you’re just a fan of The Chessmaster series, I’d love to hear from you. Together, we will complete the true story of the Chessmaster.

Rest in peace, Will Hare…or should I call you The Chessmaster?

See Also: Ask the Chessmaster (2011)
See Also: VC&G’s Halloween Video Game Costume Ideas (2008)

19 Responses to “The Chessmaster Died in 1997”

  1. MadPlanet Says:

    Well, I can’t claim any inside knowledge of Chessmaster, but I was a big fan of Chessmaster 2000 on the C64 and a few years back rediscovered my love for the franchise with a dirt cheap copy of CM 10th Edition I found at Half Price Books. So I quite enjoyed the writeup. Thanks!

  2. Jason Says:

    Nice research. I agree that the Chessmaster photo is one of the most memorable examples of computer game box art ever, though I doubt the people who created the box thought much of it at the time.

  3. cifey Says:

    Fortunately his consciousness has been replicated in many different video game disks and will thus live on for quite some time. Definitely a fake wig and beard though.
    Also I’d say his king position is quite precarious in that picture except he seems to have completely wiped out his opponent, though there should be at least the oponent’s king somewhere.

  4. Squarebie Says:

    I`d have been just starting my second decade on this planet when Chessmaster 200 was released and it was AWESOME!! And back then,
    “computer couldn’t play chess”, so it was kind of a big deal, if I remember correctly. I also want to say there was a connection to the future Deep Blue, but it was likely just a pop culture slash fading memory type connection.

  5. Rebochan Says:

    Wow, I was just thinking about this guy the other day. Hell, MST3K even included a “Chessmaster 2000” riff on a look-a-like actor during their hallowed run, so obviously he was quite visible. We may never know whether he was aware of his little bit of fame, but thanks for finding what you could 🙂

  6. jepflast Says:

    That’s awesome that you found him! Very cool to know.

  7. Hugh Jas Says:

    Chessmaster, eh! Sargon chess or get out!

  8. Ben Says:

    I remember that dude from Chessmaster 3000… back in the day when I thought the object was to get your king to the other side of the board… Needless to say, my games never lasted for very long…

  9. Ron Says:

    Far too late to say RIP

    He is handsome like some powerful wizard !

  10. Don Laabs Says:

    Hey, Benj, it’s always great to see that the Chessmaster is so fondly remembered. My name is Don Laabs, and I ran the Chessmaster business from 1988 to 2000 (CM 2100 to CM 7000). Since I’m the one who added the Chessmaster trivia to Will Hare’s bio, I thought it would only fitting to provide some more tidbits.
    Les Crane, Toolworks CEO at the time, had done a lot of work in television and knew Will Hare. The crystal chess set that Will posed with was purchased from an LA store, then returned after the photo shoot.
    Will didn’t have a special contract – he would have just been paid for the day and he likely did it as a favor for Les.
    The Will Hare photo was used until CM6000. There was a version, CM4000 Multimedia version where someone accidentally on purpose reversed the photo, and it looked awful. Never again.
    For CM6000, a new painting by SciFi artist Gary Ruddell was commissioned. Gary Ruddell is based in Marin County, CA and has done dozens of book covers and Magic: The Gathering cards. The painting was based on the Will Hare photo, so it was still Will Hare, but it looked a lot better and more modern.

  11. jepflast Says:

    The Chessmaster has a Bacon Number of 2.

  12. Geoff V. Says:

    Very cool info. I have a copy of CM with the reversed (mirrored) image of Hare. I think it is CM4000 “Turbo” multimedia edition.

  13. Benj Edwards Says:


    It is great to hear from you. Thanks a ton for posting all that info. I was hoping that a post like this would bring out someone with insider knowledge of the Chessmaster, so I’m glad you showed up.

    I wonder who owns the original crystal Chessmaster chess set now. They probably don’t even know they have it.

  14. Charlie Says:

    Why don’t you just track down who his Entertainment agent was, or what agency represented him? If he was a paid (presumable SAG Union) professional actor, he must have had an agent where records were kept….

  15. r1j1k Says:

    Chessmaster on Famicom clone made me love games. “Tha game is a draw” popup and that specific end-turn sound are the best memories deep in my heart.

  16. herbie53 Says:

    I always wanted to know who he was, now I know.

  17. HolyGrail Says:

    The chess pieces they used was the Swarovski Chess Set.

    It was designed by Max Schreck. The glass chess board is 13½” (345mm) square and the chess pieces are made from clear and jet crystal. The chess set was introduced in 1984 and discontinued in 2007.

    Here is a link to some pics of the board.

  18. Marboy Flores Says:

    You are the best teach me how chess.

  19. Chessmaster 1200- Says:

    Going through the images (also because of the MST3K riff from Merlin’s Shop of Horrors… ahem 10 years after this post *cough*) I saw this one a full 2-page spread of robed Hare carrying a chessboard: The Chessmaster 2000 Covers (DOS):,3068/

    P.S. And, Wozniak does indeed rock!

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