Arts n' Crass
This might be my favorite episode in the entire series. Only "Lane Miserables" and "Boxing Daria" can seriously challenge this one for the top spot.
Despite this, I'll acknowledge that "Arts n' Crass" is actually pretty typical for a Daria episode. It's the standard situation in which Daria and Jane encounter the school's institutionalized stupidity, subvert it, and celebrate with pizza. Where the episode shines is in its execution. The dialogue is on point, the characters reveal their best (or worst) qualities, and the conclusion is satisfying.
The theme of the episode is self-expression, specifically in how it applies to students. Teenagers don’t necessarily have the experience to understand the larger social context in which they live (admittedly, this is true for many adults as well), so their self-expression may be offensive, clumsy, or disruptive. Which isn't necessarily bad—but it can be a problem in an institution like a school, which needs to maintain a certain degree of conformity in order to function.
On the other hand, schools in the US (at least back then) made some pretense to preparing students for living in a free society, which meant they had to appear to encourage self-expression. Hence, the art contest tries to draw in the students' desire for self-expression, and then co-opts it for the purposes of school propaganda.
So you have the forces of free expression (Daria and Jane) arrayed against the forces of censorship (Principal Li and Mr. O'Neill). As is often the case, the former group has to be a lot cleverer in order to win, since they don't have the power. But they can, judo-like, subvert the power structure.
Jane features heavily in this episode, but despite this, it almost feels like she's just along for the ride. The idea behind the painting, and its incendiary caption, all come from Daria.
You can see this in Jane's stammering explanation to Ms. Defoe's interrogation. It's clear that Jane focused on the artistry without giving too much thought to the underlying purpose (granted, she corrects this later on).
It's interesting to see Daria become so invested in this. Though she came up with the concept, Jane did a lot more of the actual work.
I think this says something important about the characters. Self-expression is essential to Jane. There are aspects of herself she wants to explore and reveal, and the mere act of doing so is important to her.
You can even see some cases of this that don't involve art, like her transformations in "The F Word" and "Life in the Past Lane". Likewise, she tends to lose some interest if the art isn't hers. That's the big problem she runs into in "Art Burn".
So is the painting in "Arts n' Crass" really Jane's? She only made it because Ms. Defoe asked her to. Including Daria seems almost like a way for Jane to stave off boredom. Daria is the one who becomes more invested in the work. Jane goes along with her, since the painting still reflects her worldview and interests, but she doesn't think it's truly hers because it isn't.
Also, consider that Jane's the one who seems to come up with the idea of defacing the painting. Enthusiasm dawns on her face the moment she suggests breaking the system. In a real way, the defacing is the first time in this episode in which she's able to express herself. She can defy both the schools constraints on her art, and Daria's interference.
Daria is much more analytical and critical than Jane. While Daria may not have a strong emotional connection to the outside world, she's definitely interested in it as an object of study. Thus, for her, Ms. Li's interference feels a lot more personal. Daria used Jane's painting to say something, and it's essential that this message is communicated.
Except I'm not sure Daria communicated her message all that well. When Ms. Defoe sees the painting, she initially assumes that it's mocking or judging those with eating disorders. Those are not unreasonable conclusions. Nothing in the painting or the caption offers sympathy for the girl, or explicitly critiques the social system that would drive her to bulimia.
In fact, given Daria's penchant for dark humor, I can't help but think she intended it as mockery, if only subconsciously. Consider the painting's genesis: all the ideas Daria and Jane come up with involve criticizing and insulting the aspects of school that they hate. Their goal is more to subvert the school propaganda than to make any statement actually supporting those with eating disorders.
But Principal Li and Mr. O'Neill aren't really any better. They don't object to the painting being unclear or mean-spirited. Rather, Li doesn't want the school to look bad, and O'Neill just wants to avoid conflict. Their desire to interfere is selfish. Ms. Defoe was the only one who actually saw the problem, but she didn't follow up on it.
There's plenty of cynicism to go around.
- Interestingly, Principal Li and Mr. O'Neill act as a mirror image to Daria and Jane. Li is all about the message (specifically, the honor and glory of Lawndale High), while O'Neill acknowledges the value of self-expression, but screws up due to his noxious half-measures.
- Both Jake and Helen have great moments in this episode: the former in his defense of Daria's artistic integrity, and the latter in her epic takedown of Ms. Li.
- Upchuck is a surprisingly skilled artist.
- I'm pretty sure this is the first actual episode of Daria that I watched. As someone who's been a Type 1 diabetic since age three, Jane's "Not if you're diabetic," line made me a fan for life.