Shinkai’s films, while usually breathtakingly beautiful, are all intensely depressing and sad. He has been dubbed “the new Miyazaki” by many in the anime biz, but he considers that to be an exaggeration, as do I. His films are very deep, beautiful and well done, but as such are not really comparable to the generally family fare that comes from Studio Ghibli. They are also all fine for family viewing, if your family likes watching depressing and long anime movies.

The Place Promised in Our Early Days (2004)
Kumo no Mukō, Yakusoku no Basho (雲のむこう、約束の場所) (lit. “Beyond the Clouds, the Promised Place”)

Shinkaisan must have a very depressing love life, because this movie once again portrays a love so deep that it transcends multiple literal dimensions. At only an hour and a half, this movie does unfortunately feel long, but with the superb animation and a love portrayed that quite literally knows no bounds, this film is pretty much guaranteed to not only be worth the ride, but touch you in a non-suggestive way that only such a profound story can. I definitely cried and you probably will too during effthe last few minutes of the movie. Positively beautiful and recommended most for watching with a significant other.

5 Centimeters Per Second (2007)
Byōsoku Go Senchimētoru (秒速５センチメートル)

Another in the line of Shinkai’s depressing masterpieces. This one is split into three unequally sized sections that depict the rather sordid love between a boy and a girl and how the distance and time between them affects their relationship. Don’t expect a happy, happy fairy movie here at all. The first part made me cry a bit, but the entire piece taken as a whole is even more depressing. Very much worth the emotional ride for not only the superb animation, but also the very deep kind of love that only Shinkai seems to be able to depict on screen. The sorrow portrayed through this work is palpable and made very real for the viewers. Not a movie for depressed people, but a stunning piece for the anime buff and romance enthusiast alike.