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Perhaps my first thought about many identity-left people when I've spoken to them has been "Why are the things they like and find entertaining so weird". It was like peering into a mindset and a type of culture that was entirely alien to me and that I still don't feel like I understand well on a base level, and this might be the first comment which I've seen acknowledge that the tastes of many people in the left are extremely distinctive and reek of an attempt at social signalling (to others, as well as to themselves).
A huge portion of their entertainment shares these ironic, deconstructive, absurdist characteristics you mentioned, sometimes with a very heavy dose of blink-and-you'll-miss-them references most of which exist primarily to confer insider/outsider status. The same goes for many of the memes they enjoy, which are these weird maximalist parodies of memes that kill my brain and seem almost exclusively like an assessment of whether one exists on a sufficiently high level of irony to understand the joke or not. Quite honestly, my level of disdain for a good amount of this kind of entertainment is off the charts, and I can't imagine anyone enjoying it or engaging with it on any real level. My disdain for it is not inherently because it's "nerdy" or exists outside of the mainstream - there are many strange cult pieces of entertainment I very much enjoy, probably more than the vast majority of mainstream entertainment - but rather because the types of entertainment I'm referring to don't seem to serve much of a purpose outside of denoting those who consume them as being an outsider. There doesn't seem to be much genuine love or vision behind the piece of work itself.
As you note this attitude also jives with the general viewpoints of the woke left, too. Their entire political worldview exists in opposition to any stable or traditional cultural structures, and continues to do so even after these cultural structures bend to them. They see themselves as being politically ascended in some sense, having "realised" that the overarching culture is intractably patriarchal and white supremacist, and thus they have to take it upon themselves to educate the unwashed masses about how everything they do perpetuates prejudice because of their superior understanding of social dynamics. Red-tribers especially are portrayed as being reactionaries, which is a very meaningless term in my opinion (since opposing change isn't inherently negative) but in the Blue Tribe the implication is that any pushback against the supposedly unequivocally positive changes they want to implement exists simply out of ignorance or fear.
The particularly notable thing to me is that much of these leftists' sense of being an outcast who looks down upon the normies can persist long after their viewpoint and sense of aesthetics become culturally entrenched. That type of self-aware, absurdist, deconstructed entertainment has become fairly widespread, but these creators and their audience do still try to portray themselves as being on the cultural fringe, the very same way wokesters think of themselves as being counter-culture revolutionaries despite their beliefs basically being the dominant view within the mainstream at this point. They would think of me as being part of the cultural hegemony and them as being outside of it despite the fact that the very opposite is true. They're perpetually able to look down upon the mainstream, even when they are the mainstream.
Could I ask you to name some names regarding what's popular with the woke?
In my last brush with the New Orthodox Woke during the start of the pandemic, the stuff being pushed was Infinite Jest, Waiting for Godot, Blue Velvet, and anything Southern if it was to do with a black person, ideally a black person who had been lynched. Also, they keep saying they love D&D, but then refuse to play because the setting contains racial prejudice.
I do think there are certain things which are pretty appealing in a widespread manner. However, when you see the types of entertainment that does have a huge skew where the fanbase appears to primarily be of one political tribe, it's very notable how distinct they are.
I wasn't going to bring up specific examples because I think any specific discussion will invite some very vehement disagreement by people who happen to enjoy anything I lambast, but here we go.
So I used to be pretty involved in music communities, and a genre with one of the most overtly woke fanbases I can think of is PC Music/hyperpop (the most notable of these artists being SOPHIE). Example here. For those who are unaware of what this is, it's basically an ironic/post-ironic caricature of pop music which exaggerates every single one of the criticised elements of pop. The aesthetic of their music and music videos and entire public image exemplifies sterility, artifice, almost sickly cuteness and has a very strong undertone of cynical parody to it - basically nothing about it sounds genuine, and I think that's the point. Another factor that also probably helps to attract leftists is that a huge proportion of the artists making PC Music are part of the rainbow community.
Other artists that have a bit of a strange outsider aesthetic, even those I like, also tend to have a primarily leftist fanbase. I can testify to being kicked out of an Autechre discord server after expressing wrongthink once during a political conversation (which I did not start). While I enjoy their music quite a lot myself I can also testify that a huge amount of their fans are extremely woke and also tend to be quite the pretentious type.
Then there's games. I'm currently watching a friend play through Disco Elysium (a game with a fairly strong leftist bent to it that kind of plays out like a postmodern novel) with a group of other left-leaning friends. It's got style in spades, and I don't doubt that care was put into this, but at the moment my perception of it is that it's a pretty slow and artsy game which I can't help but regard as being quite difficult to like. It comes off as a bit of an unfocused mix of political satire, philosophical musings and absurdist nonsense all of which don't really blend into the murder-mystery narrative well. My opinions might change later, but I'm not too optimistic about that.
For film, I’ll just refer to a huge portion of A24’s output. Their films resonate with that same audience, the type who like artistic slow burns.
There are more I could include, but these are the first few examples that come to mind. And it's not even that they're always bad, either. It's just that in most of these cases, the people who consume them are often the type who tend to like distinguishing themselves from the normie crowd, and who see themselves as being part of a distinct, unique, subversive subculture that is new and revolutionary, one which is simultaneously aesthetically superior to and yet ignored by the normies. There's a certain amount of elitism that comes with the territory which doesn't seem to have been nearly as prominent in OG nerd culture.
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I like weird stuff, but I don't consider myself that far to the left. I guess political lean could proably be weakly predicted by tolerance for weirdness in media (I say weakly because the more esoteric parts of the right (such as the Dissident Right) seem to be...well, rather strange).
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So, I do want to make it abundantly clear that I am a genuinely passionate decades-long fan of Weird Al’s work, and if you’re accusing him specifically of lacking a sense of love and vision, I think that accusation is baseless. I’m intimately familiar with the world of pretentious, artificial status-signaling art you’re referring to, but I cannot stress enough that Weird Al’s work, like his life as a whole, has always been characterized by a palpable sense of joy and authenticity. The people in that room last night were, overwhelmingly, not there to impress anybody or signal status. Al’s work is far too lowbrow and affable to appeal to genuinely pretentious “artsy-fartsy” people, and being a Weird Al fan carries no cultural caché. He’s basically only respected by a) comedians, who largely revere him both for being a legendarily nice and wholesome human being, and b) Gen X and millennial white nerds who wouldn’t enjoy an arthouse film or post-modern novel any more than you would.
Your points as a whole are astute and absolutely well-taken, but I cherish Weird Al too much to let anything I’ve said give the false impression that he himself is a sneering progressive MAGA-hater. I’m confident that his personal politics are standard-issue Gen X California liberalism, but he’s certainly not shoving that down anybody’s throat, and he happily plays to audiences in Red states and Blue. I’m just saying that his work carries a set of implicit themes that naturally appeal to a subset of the population to whom culturally-left politics also appeal, whether or not he has any conscious intent for that to happen.
I did pick up on that and am not accusing Weird Al specifically of anything (I wouldn't be able to, anyway, since I am not familiar with him or his content whatsoever). For my part, I'd also like to clarify that there's content I enjoy myself that shares some of the deconstructive/absurdist characteristics which appeal to the cultural left, but the ones that appeal to me are those that seem to have more substance and where the creator has something to say outside of dead-eyed detachment. It's the stuff that seems entirely hollow and alienated that I have a serious disdain for and exemplifies all the worst things about that kind of aesthetic.
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