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I've thought about this a lot in the context of the observation "the left can't meme". The idea is that memes (or jokes more generally) advocating a woke or leftist worldview tend to be less funny than apolitical memes, or memes advocating an anti-woke, classical liberal or conservative worldview. An alternative phrasing applies it to creators of memes rather than the memes themselves, so that even an apolitical meme created by someone known to be woke or left will tend to be less funny than an apolitical meme created by someone who isn't. Anecdotally I think this is a very accurate description, and most leftist memes (and jokes and comedy more generally) seem intended to provoke clapter rather than actual laughter. In some cases, "stand-up comedy" in which the audience isn't supposed to laugh (which we might have traditionally called "spoken-word performance" or "lectures" or "sermonizing") is the explicitly intended point.
For argument's sake, let's assume the premise of the meme. Why is woke/leftist comedy less funny than other kinds of comedy? Your point is essentially my explanation for the phenomenon. Effective comedy and humour depends on creativity and the element of surprise. Wokeness depends on absolute ideological conformity and rigorous adherence to a set of linguistic prescriptions which are essentially arbitrary ("coloured people" is out; "people of colour" is in), vary depending on the perceived identity of the speaker (who has "N-word" privilege? Does the one-drop rule apply?), and subject to a euphemism treadmill which seems to accelerate every year. It should come as a surprise to no one that comedians cannot reasonably be expected to serve two masters.
And it's no good telling these comedians "just write the funny jokes, then go through them with a fine-toothed comb and replace all the naughty words with items from this official list of PMC and HR-approved ones". Replacing a single word in a punchline can be the difference between uproarious laughter and dead silence, as any skilled standup comedian knows. But at a deeper level than that, we're talking about habits of mind. Once you get into the habit of obsessively overthinking and analysing everything before you say it, walking on eggshells for fear of saying anything which could be taken as offensive, the funny jokes simply won't occur to you anymore. It's impossible to write a funny joke when you're living in mortal fear of your career being destroyed because you couldn't remember whether you're supposed to say "unhoused person" or "person suffering from unhousedness" this month.
Comedy is, by its nature, subversive. It doesn't have to be politically subversive necessarily, but it needs to subvert expectations. Taken to its extreme, like Andy Kaufmann, it can even subvert the idea that a comedian is supposed to tell jokes.
The problem with woke comedians is that they are limited. Their worldview is dominant. So woke comedians like Amy Schumer are boxed in. They can't tell jokes about politics. They can't tell jokes about society - not funny ones at least. So they try to mine the existing sources of taboo they can find, for example toilet humor. But it's all been done a million times. We basically expect female comedians to make jokes about their vagina nowadays. That's why those jokes never land and Amy Schumer is cringe as fuck. But it was probably mind-blowing in the 1970s or whatever.
Being against the current paradigm lets you be funny in a lot of different ways. Being for whatever's cool now is by definition not funny.
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By and large no-one can meme, at least if the goal is to meet the exacting humor standards of extremely online weirdoes who have fried their brain with a mental diet of years of image boards and other social media.
Your modal right-wing meme is not "dissident humor", it's a boomer uncle posting a picture of laughing Minions with a Comic Sans text "How is it that the Left wants to tell you what to think, when they can't tell a girl from a boy?"
Speaking as an extremely online weirdo who has fried his brain with a mental diet of years of image boards and social media, it really isn't that hard to make me laugh, chuckle or smile. If I scroll through my Instagram feed for ten minutes, I can reliably expect to laugh at at least one image I see, whether it's a meme or a screenshot of a tweet or a silly video. (I would say the overwhelming majority of content that makes me laugh isn't political at all.) And yet this is a bar that explicitly woke/leftist memes, jokes and standup consistently fail to meet. Oftentimes the purpose of the ostensible joke seems less about making the audience laugh (even in a supercilious "ha ha our opponents are so lame and stupid" way) than merely signalling allegiance to the cause i.e. clapter.
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Even assuming wokes and dissidents are equally endowed with humour, the political domination of the former creates a selection effect. Any leftist joke, funny or not, is allowed to spread. People repeat it, if only to signal conformity and obedience. But non-cathedral-approved funnies face suppression, and only the most laughable survive. One will share them only if their quality outweighs the social cost imposed on the sharer for outing themself as enjoying egregious entertainment.
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