Actually, let's leave the Marx Brothers out of it. For me their movies go straight into Room 101. And also forget about Kafka and Sartre, who after all didn't write about the kind of purposefully malevolent state ruled over by a guy like Stalin, for whom death quotas and torture were part of the apparatus of effective government. The torture of existence in a Kafkaesque society comes from running up against people like this.
Okay, so we're talking about truly unrelenting totalitarian regimes. Is there humour to be found there? Any unchallenged political ideology will soon make paranoia the default mental state of the entire populace. To drive home its beliefs against the flow of common sense, the regime is willing and able to twist logic into unrecognizable Escher-shapes. Law becomes corrupt, identity disintegrates, truth is raped and ruined. Living in such a warped society can eventually push anyone to the kind of hysteric laughter where you want to claw your own face off. Satire may thrive, but this article suggests that it's fuelled by an uncomfortable sense of humour with a distinct smack of sweaty fear.
In North Korea, high-ranking officials would dive into the shrubbery when they saw Kim Jong-il coming. Better to risk a grass-stain than to run into the Supreme Leader in a bad mood.. It was a riot as long as he didn’t spot you. Under the bloody rule of the Khmer Rouge, men and women were beaten to death by screaming guards because they were spotted reading the labels on an orange crate, an act of subversion that showed them up to be dangerous intellectuals. See how easily that could become a gag on Mrs Brown's Boys? I don't even want to get on to the excesses of ISIS, wagging a finger in the air on YouTube as they mansplain why sawing people's heads off is a righteous act. The ghastly comedy there is that apparently one under-35 Briton in seven sympathizes with them. Hydra should be out in London recruiting right now.
And there’s an arsenical lacing of humour in novels like Koestler’s Darkness at Noon and Nabokov’s Bend Sinister – even humour of a Milliganesque sort – but that taut grin curdles into a rictus of horror when the characters rebel and the regime exercises its penchant for casual, heart-stopping brutality. It’s Brazil without the comforting zaniness.
So, how to use all this in role-playing? For starters I wouldn't even attempt a sustained campaign, because the players would either have to side with the regime, which will pall pretty quickly, or they oppose it, in which case they will be crushed. (You could allow them to lead a successful revolution, but that would be fake. We all know people like Stalin live to see the good guys buried and then go off to die in their beds.) James Wallis's Alas Vegas provides a good template. There the campaign is planned to run over a set period and to reach a definite conclusion, the way a cable TV drama (say The Shield) aims to tell a given story rather than extend off into infinity like network serials of old (Columbo, etc). The end is going to be bloody, but there are all sorts of ways to die. It's up to the players to find whatever scrap of triumph they can in this scenario.
As for humour, I don't see it as my role to build that into the tone of the game. In fact playing for laughs is the surest way to make the whole experience deeply unfunny. (See reference to Mrs Brown's Boys above.) No, I'd be inclined to run it pared-down and very bleak, like having dinner with Pol Pot when he has a migraine coming on. I'm confident that my players would find humour in the gaps between tragedy and horror - and, arising out of character, that comedy would have the ring of truth. Which is really the whole point of role-playing.