Six-Chamber Champion

You’re in for an illegal game of Russian Roulette—you leave a millionaire or you don’t leave at all. The referee and the crowd sees to it that you and your opponent play by the rules.
For obvious reasons, even at its longest this game is very short.

Only, I’m not sure that this really is what you would call a game. It is, however, one of a growing number of IF works where you play a character with goals (or motivations or preferences or values etc.) that you, as player, find objectional and are unwilling to promote even in and for the sake of gameplay, works whose value resides in something other than being fun.
Gijsbers’s The Baron and nespresso’s rendition are, perhaps, the most famous and infamous examples, respectively, of this trend (if it be a trend) of IF.

Not being fun presumably has little to do with the objectional character of what (fictional) actions the player needs to let the PC take: you may, e.g., not feel the least tempted by a life like Niko’s in GTA IV but still enjoy the game; or you may honestly disapprove of Lottie’s schemings (and never actually have gone to quite her lengths yourself to secure your career) and still findBroken Legs great fun: rather, I suppose, it has to do with gameplay.

I.e., the author of this kind of IF has to do the opposite of what is usually done in games. He has to make sure that the player will not be so immersed in the gameplay, i.e. so keen to win the game, that he/she starts having fun (which would make the player insensitive to the moral issues of in-game actions). This does not mean that the reader/player can’t be allowed to be interested in the story as told nor identify or sympathize with the PC.
And, of course, even though such a piece of work mustn't be fun it needs other good-making characteristics to make it worth playing.
So, the player needs to be at once (sufficiently) alienated from gameplay but not from the game itself (or he/she would just quit playing it).

One way to achieve this is to make a rather ordinary game but basing it on actual events that still retains a traumatic impact on people’s minds—indie video games such as Super Columbine Massacre RPG! and Operation: Pedopriest tries this. The trauma serves to alienate you, but ordinary gameplay lures you on (with perhaps some social message or satirical lashes added for good measure). The end effect, I guess, is that the player oscillates in and out of an awareness of the abhorrent character of the PC’s actions.

The Baron works quite differently. The estrangement here comes, I think, from a feeling of disappointment in or betrayal by the PC; whereas what makes you keep playing/reading is partly the story (you want to know how it ends) and partly (perhaps mainly) an interest in the exploration of the complex moral issues raised by the … game(?).

In Six-Chamber Champion, as in rendition, the alienation from gameplay is rather more thorough than in the above examples. Even game mechanics serve to alienate you from it, being mostly repetitive or variations on a very limited theme. The rules of russian roulette just don’t allow a vast range of subtle tactics. (And rendition doesn't give you much choice either.) Also, you are given hardly no background at all to what brought the PC into the situation in either of these works.

So what remains? Why play such a game?

Well, in the case of rendition, there is of course the political message, but having a political message is hardly enough as far as good-making characteristics go. Actually I never could bring myself to play very far into rendition. Perhaps it’s an interesting experiment rather than good IF.

Six-Chamber Champion I found worth playing through, though.
The reactions of the blood-thirsty audience, the anguish of your opponent, and the heavy cool of the referee are all very well characterized (I was not equally convinced by the PC), and most actions you are likely to take is appropriately implemented.
I doubt that I would like to play my way through a whole tournament of russian roulette like this—even if fictive. But this piece is wisely confined to a single round. Small, in this case, is beautiful … or at least a virtue. Despite the limited size of the work it contains a number of possible endings, and I replayed the whole thing a couple of times to find them.