In popular media, "Harvard" is cultural shorthand for an elite institution, a place where genius congregates, and if its a comedy, it's usually a distinction between uptight self-serious frauds, and a graceless accidental genius. In this way, popular classics like Legally Blonde or even like Gilmore Girls drills down to the real problem with the Ivy League in the first place without really going into how all this comes to be (which isn't the job of media like this to do– that it's an unflattering character study about the people isn't terribly problematic to me). The locale in these media are so generalized that most people who think they know what Harvard looks like are probably more familiar with the University of Toronto campus or community colleges in the Pacific Northwest that stand in for it, in this media, and that's also fine, again, not really the point.
The alternative is media that not only has little respect for the people, but the institution as a concept, and the media produced in this vein is probably much more relatable to the average person, which is decidedly an anomaly when you discuss comparisons of relatively niche publishing to blockbuster movies or shows that Netflix has made millions on in streaming old episodes of. I have a couple of example of this genre: Teddy Wayne's novel Loner, Elif Batuman's The Idiot, and we could even look at something like Keith Gessen's All the Sad Young Literary Men.
What these novels share is just an incredibly mundane locale, much like any college, it reminded of my own (state) college I attended, much like it probably did anyone who attended not just Harvard but any school from the 90s through probably 2010 or so. The point being that the school was no big deal, notable for attracting a mix of sociopath social climbers (Wayne), self-serious but ultimately kind of off-putting former gifted kids (Batuman), or those who relish the space to be academic while ultimately the enrollment being an exercise in coercive professional networking (Gessen). All these books are about so many more things than this, but these aspects are present. To the extent that each of these books has failure from those who expected to never struggle again, at least not in the way normal people do (Gessen, for example, famously always felt the life of a writer was one that rarely was glamorous, but there's actual normal people failure depicted in the novel for example from many of its Ivy educated characters). In Batuman's book it's a lot of people realizing the conceptual basis of imposter syndrome, and the various responses some have to it (dangerous overconfidence to compensate, over-self-criticism, etc.), and in Wayne, it's the story of a maladjusted incel-type personality. All of these share very authentic depictions of the experience of attending such an institution, if all the critiques are to be believed as well.
As a spectator, just as you might cheer on some rich failson who would otherwise graduate into a profession where they could coast on their pedigree forever being steamrolled by Elle Woods, these stories ultimately make entertainment of these people simply falling flat on their face. Less the case in Gessen, where the failure is more existential, less abstract, and less about pedigree as much as being normal people doomed to normal people failure while also having the misfortune of needing to compare yourself to the daughter of a Vice President for example, which is its own kind of rewarding if you dislike the idea that one can simply traverse the right social labyrinth to wind up being thought better of than someone who probably worked harder, the Wayne text is overtly about someone who thought Harvard would make him appreciated, but as he learned, he's just genuinely unpleasant to be around and, as it turns out, a really big piece of shit who gets preyed on by someone with an equally challenged moral compass. Different brands of sociopathy, one that Harvard can pretend to discourage while allowing to continue and one that must be prosecuted criminally, but sociopathy nonetheless.
Ultimately, you feel the most bad for the characters in Batuman's novel because it's genuine, you understand the mental traps they've fallen into throughout the narrative even if nothing really makes you feel good that it happened to them. It's not that you want these people to suffer, one could speculate the people who do consume this type of story as entertainment do so because it is equalizing, humanizing (rather than, someone self-serious might argue, dehumanizing in gathering to laugh), you realize they're being encouraged systemically/institutionally to be a certain type of sicko at the top of a given field after graduation at some point in the future. It's the least amount of pressure for many of these people that generates the most stress that drives a lot of these people insane; the protagonist in Wayne's novel is a good example of this, the experience of leaving an elite institution for some of the characters in Gessen, and just the uncertainty and doubt about of Batuman's characters' decisions are they weigh passions and what they feel they should do either by careerist lenses or peer scholarly value.
The flip side of all of this, with ostensibly the same moral message (that you're a human and worthy of respect and love and moments of triumph amidst nothing but objective, by the standards of your society, failure) are films like Little Miss Sunshine or The Way Way Back where people if you had their lives you might actually be more content with than your own, but in the framing of the film, you're meant to understand their lives are something they feel is substandard, something broken to some extent– the suicidal Proust scholar of Sunshine being an example of the kind of failure I'm describing in the first part of this piece, ironically enough- but healed by experiencing trauma and struggle together only to realize their sense of self-worth shouldn't be informed by failing to meet an aggro-sense of needing to meet a moving goalpost, but informed by the enrichment of your life by your loved ones, and theirs by you.
Stalin once wrote, “It is not heroes that make history, but history that makes heroes.”– this is the stock position of historical materialism, and it applies to the class struggle of Americans, both to whom it treats favorably in general and those it decidedly never does. It makes you feel pleasure at seeing those who would relish and be enriched by your failure become failures themselves, but it makes you feel love for one another to see those who embody you make something from nothing but pain and struggle, and as Stalin also said, “I believe in only one thing,the power of human will.”– what does a class of those who suffer and only have each other to rely on stand to build, what do they stand to gain; virtually everything required of a rich human existence, it turns out.
In both these sets of media, there's a qualitative argument to be made– the means and ability to either thrive at an elite institution, or toil in obscurity, or just exist as a person who deserves a home and care and community, as Stalin puts it, “Quantity has a quality all its own"– and so it does; the material conditions of each of these stories plays a role in shaping the perspective of each of these Harvard students (a working class immigrant, an immigrant who is the child of scholars, a middle-class kid from middle-class American parents) or of the family in Little Miss Sunshine (regular people who are all brilliant in their own ways, and absent access and resources, feel they cannot be more than they are given).
What motivates all of these characters, whatever motivates the reader or viewer, I think the sentiment is the same; we are loathe to participate in this society, some tolerate it better than others, some tolerate tolerating it better than others, some tolerate rejecting it better than others. In the prologue of Open, Andre Agassi writes what I think is the most succinct expression of why anyone does anything in our society, when they hate it or they love it, describing himself in pain unable to join his family at the breakfast table and trying anyway:
"Hate brings me to my knees, love gets me on my feet."