Is there a solo computer chess program where you can play against imaginary/fictional/historical characters (and maybe win once in a while)?

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Chessmaster is such a program. It is a bit outdated now, but still very usable for the majority of people. The skill cap for the game is well beyond what most club players will ever reach in their lifetime. Some examples of opponents you can play

  1. Imaginary - You can play in a Human vs Orc arena, against a commander of the opposing army. There are limited difficulties in this level, so you may have problems playing against the harder opponents. It is also not explicit about which opponents are hard, and which ones are easy, so you will have to test this yourself.

  2. Fictional - There are hundreds of fictional people to play against. Each of them have a biography (if you care to immerse yourself) and a picture of a person to help you believe you are playing against an actual person. There are a wide variety of playing styles to help simulate the different kinds of human players you might play against.

  3. Historical - There are many famous players who have been simulated into the game, including various versions of Josh Waitzkin at the age of 6 and beyond. Most of the historical players however will be playing at the maximum skill level of the game, since it will be trying to simulate the strength of Grandmasters.

I'd recommend playing against the fictional players, as they are entirely beatable once you learn the rules. You will start out with a rating (around 800 if you are new) and your rating will adjust as you play a few games.

Don't be disheartened if you lose your first few games, this happens to everybody. If you are serious about improving, you will learn something from each loss and eventually your rating will improve, and you can play against stronger opponents.

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