Spoiler Inclusive
Good points:
1. Back in 1998, Shoujo series followed the format of either Rose of Versailles or Sailormoon. Those were the big too but Kare Kano broke out with the third format that more than half of all Shoujo animes since followed - wacky fun romantic comedy. Gone was the drama and magic, in was the crazy comedy of highschool romance. It might not seem like much as Shounen romance had already begun this shift long ago with Urusei Yatsura in the 80s but for Shoujo anime it was a big leap. And even now, 15 years later, Kare Kano can hold it's head as being one of the funniest Shoujo animes in history.
2. A number of cliched plot points or settings in Shoujo anime was created by Kare Kano, the main one being that a girl has her secret found out by a bishounen, who proceeds to tease her until they start dating. Also Kare Kano started one of Shoujo mangas dreaded trends - after the main couple form, the story focuses on only two things. Firstly on having superficial drama from random love rivals and misunderstandings, which are neither clever or inventive nor interesting. Secondly by having every single character with more than 10 lines find a soul mate as well. This trend is in Lovely Complex, Kimi ni Todoke, Special A, etc. Many good Shoujos that were extended endlessly by this stupid idea. However Kare Kano did not fall into this trap initially. As most of the series occurs after the couple forms, the story maintains its interest with a strong selection of characters and believable problems with proper drama and character development. It's astounding that the original could do what it's copy cats failed to do.
3. Hideaki Anno and Gainax are both Kare Kano's strength and weakness. Getting to the weakness later, the strength they brought is by turning a popular Shoujo series into a Shoujo version of FML, in stylistic view. This was Hideaki Anno not long after finishing End of Evangelion. It might sound impossible to imagine how he would tackle a Shoujo romantic comedy but it is actually very simple - he did exactly what he did for Evanglelion to Kare Kano, while adding Gainax's typical zanniness for comedy. This is what Kare Kano has that few Shoujo since has. It is as brooding, melancholic and thoughtful as it is fun. Hideaki also brought is artistic style for static thematic backgrounds with him, which adds flavor to the series, at first. Hideaki's touch made Kare Kano into something the manga was not, which is both a good and bad thing.
Bad points:
1. Kare Kano's problems start and end with Gainax. I don't know who managed the company's accounts in the 90s but they should have been fired after the fiasco that was episode 25 and 26 of Evangelion. Gainax's budget problems were as legendary as their most famous animes and it reared its head throughout Kare Kano. After the first 3-4 episodes it becomes clear that Gainax realize they are going over budget, so in pops 2-3 minutes worth of recap at the start of each episode. These recaps are at first done with variation in style and voice acting but soon become extremely poor with actions on the screen not matching the speech through the speakers. Entire episodes dedicated for recap and extreme recycling of scenes proceed.
2. Hideaki Anno gave Kare Kano something different with his brooding style, his flavor. However as the budget he had to work with grew smaller his use of that style as a flavoring turned excessive to the point where all one saw was Anno being Anno, like a soup with a little hot sauce becoming only boiled hot sauce. This is a light hearted Shoujo romantic comedy not Evanglelion and the overuse of Anno's sense felt like a mismatch. It doesn't feel right but no one was going to say anything because Anno was able to manage the budget until...
3. The mangaka herself calls up Gainax and says WTF. Her beloved work was being turned by Anno into something it wasn't. She didn't complain when his style improved it at first but thankfully she did when it was starting to ruin it. The result was Anno quit, the recaps and lack of direction followed and all this and a complete breakdown in relations between Gainax and the mangaka lead to Kare Kano getting cut.
Kare Kano is still one of the most unique and interesting Shoujo animes out there but like anything great Gainax did (with the sole exceptions of FML and TTGL) it was hampered by Gainax's lack of planning. In many ways it's a study of taking things too far is bad.
Story 8/10 - Original at the time and still better than many of its iterations.
Art 6/10 - Visually realized at first but grows stale and recycled later on.
Sound 9/10 - A strong voice cast keeps the series and its many recycled scenes alive.
Character 8/10 - Develops characters with Hideaki's touch and thus surpasses the original at first.
Enjoyment 7/10 - a 10/10 for the first half but after Hideaki's resignation and Gainax's cash flow problems it's hard to ignore Kare Kano's failings.
Overall 7/10 - A potential masterpiece by Gainax brought down a lack of communication, budget and planning. Typical Gainax.
