Characterization. It's the strongest part of Melancholy, yet having said that, the story is filled with endless caricatures, of individuals without depth. In fact, the only two real characters in the story are Kyon and Haruhi herself - everyone else is a reflection of a particular trait or aspect of the world around them. I suppose that makes sense plot-wise - after all, everyone else was essentially conjured up by the sheer boredom of Haruhi. Instead, Melancholy replaces quantity with quality, sharing with us two pristine examples of how characterization should be done, not only in anime, but in all stories in general.
We learn of the events of the story from Kyon, a sarcastic, wise-cracking high-schooler, much like you or I might have been at that age. He's cynical, yet a hopeless romantic, blasé, yet still deeply caring when he wants to be. In essence, he's imperfection personified: a true, down-to-earth human being who is already struggling with just living out his own life (you can just hear the pressure in the tone of his voice) without having to deal with some crazy psycho-lady who believes in the existence of aliens, espers, and all that jazz. His interactions with Haruhi are akin to an older brother playing along with the facile fantasies of an overimaginative younger sister. Yet, within his nonchalant annoyedness during the escapades of the SOS Brigade, his side of caring shines through. You could imagine Kyon to be one of those guys who gets dragged along by his overbearing girlfriend to a bunch of things he doesn't really care about. While you can tell that they really don't want to be there, day after day they're still by their lady's side.
Kyon's lady is not your average lady though. Take the most out-of-touch, fantasy-dwelling, "I'm a superhero" five year-old you know, and then square that, and you might have someone who can come close to comparing with the eccentricities of Haruhi. We shouldn't blame her though, she's just vocalizing everything that we each have wondered or questioned ourselves at some point in our lives. She is frank, if nothing else, yet at the same time, much like Kyon, an image of imperfection. Haruhi is exceedingly selfish (or, more correctly, self-absorbed). At the beginning, she can't seem to fathom when anyone would not think of the world in her terms, and places all those who can't (i.e. the rest of the human race) in a category that is below her associating with. Perhaps part of that is because we normal humans cannot identify with the candor of Haruhi in our conscious state, but whatever it is, Haruhi begins the tale obsessed with only finding out who in her high school is a time traveler, or esper, or alien. Haruhi's evolution throughout is really the subject of this anime, and the way that the world is truly opened up to her by Kyon suggests the cure to all of our melancholies. By the end, she's softened up considerably, and while she still has her unique quirks of searching the universe for strange beings, she is also more responsive to the people around her in the "real world".
Unfortunately, the perfection reached by Melancholy in the characterization process is marred by the faults made elsewhere. Most notably is the anachronistic presentation of the episodes. Many fans of the Haruhi series have stated that by presenting the series out of order, it opened up avenues of creative freedom for the writers to fully flesh out the characters in a plot-limited environment. While that is true, and the development of the characters progress mostly linearly throughout the series, the time gaps and discontinuities created by the at times haphazard ordering of episodes tends to present a distraction to the viewer, rather than supporting the overarching development of the plot and characters. The most glaring fault in the continuity is dialogue - too often characters refer to events that have already happened, but have not yet been shown. And these aren't just casual references, you're actually supposed to figure out what's going on in a given episode by the back references to events that you (as the viewer) know absolutely nothing about. I still think that the series could have been presented in the way that it was, but some rewriting of the references are definitely in order, so that there is some linearity in dialogue at least, if not in plot.
My recommendation though is still to watch the series in broadcast order. Having watched it in chronological ordering, the series loses the charms of the character development. Give the wacky, loopy plot presentation a chance, and you will be rewarded by the anime with the greatest character development since, well, forever.
