My list:
Tokyo Godfathers
A clever, well put-together grown-up Satoshi Kon black comedy/Christmas film. Save it until this Christmas, I swear you'll enjoy it in all it's unusualness. Three homeless people find a baby on Christmas Eve and embark on a personal journey in the city of Tokyo. It is an ugly, frank portrayal of the characters and lives of the homeless people in the film, but EVERYTHING about the way it's done works for me. I have not seen an anime film like it, Satoshi Kon is a clever man.
Millenium Actress
Another well-told anime film of his, filmed very creatively and very different to Tokyo Godfathers, it's a serious film about the life and desperation of a woman who became a legendary actress, from her childhood to her death, living through important periods of the second half of the 20th century. It is absolutely soul-wrenching in places. And when I say "creatively filmed"... you just have to see it to understand what I mean, I cannot describe it well. This is an anime film with a genuine soul, not worthless dispensible rubbish.
Perfect Blue
Another Satoshi Kon film. If you watch these three films, I think you will be a confirmed admirer quite easily- his films are unique. Perfect Blue is a great surrealist, adult, suspense thriller. It's haunting, and very clever. I think I would recommend the other two films first now, but Perfect Blue is still a classic anime film that's worth seeing for it's disturbing, intense psychological angle.
Patlabor 2
You can watch this film of Patlabor without really knowing the rest of the franchise, and still get a whole lot out of it. If you are a fan of the original Ghost in the Shell film, it's a must. It was the film Mamoru Oshii made directly before that, and it retains the same incredible "realistic" feeling style. Asside from haunting shots of the city and intimate, introspective views into the characters and their inner-turmoil, it reflects the feelings of Oshii himself at the time, as a Japanese man looking back at recent history and wondering where they are going. I am still haunted by some of the things said in the film, and the beauty of something so personal and yet cold. Using the backdrop of a faked terrorist threat on Tokyo and it's real consequences, Oshii explores his and other intellectuals at the time's frustrations with the way those in power behave, with the status of the Self Defence Force, the bubble economy that was about to crash that some could see but no-one would acknowledge, with post-war complacency, with the relationship between war and peace... just everything. It is a film for the end of a century.
In many ways, it is deeper than Ghost in the Shell in a real-world sense. The execution is ever so slightly unrealistic perhaps (could this *really* happen?), but the message is not and it is the thing of real importance. If you have an interest in history, in how the themes and problems relate to our world today, and in normal working people with little power and a tonne of bureacracy to work against still trying to do the right thing, then this is the film for you. Plus I love the Shinobu Nagumo character, a mature female character who is not about looks or super-powers but simply plays the role of a civil servant with a past burden and an unresolved period of her life, and the will to endure and do the right thing. Gotoh is an excellent character, too. Shinobu's sadness and the city seem to resonate with each other in the film. Ignore the giant robots on the cover, this has little to do with them. It's just a very personal, unsettling film. If you watch the film and like it, buy the limited special edition- it comes with a great book that goes into the film in serious depth; I thoroughly enjoyed reading it after being in love with the film all these years.
...okay have I sold this film enough yet?
Macross Plus
Available in film and 4-part series versions (both in one convenient, cheap box), Macross Plus is about relationships and technology, and the damage the past can do to personal connections and childhood friendships. It's about redemption, sacrifice, and those who hold onto their dreams and those who don't. I think the tech aspects are cool (Sharon Apple!), and I like the way the two versions offer subtly different focuses (one more on the test pilot rivals, the other more on AI Sharon and her relationship with the fragile, shattered woman Myung who controlls her). The world it's set in is interesting, the message is inspiring and complex, and even though the main guy is a bit of a dork at times (especially in the dub) I found it didn't mar my enjoyment of the film/series at all. It's both masculine and feminine at the same time, which is a good hit for me.
Boogiepop Phantom
Intelligent, well-executed, unexpected and mature in it's messages and themes. But -if you want a break from anime-
do read the book first (Boogiepop and Others). The story of the novel is clever, it's really a rather interesting look at humanity and people and the way change works (all set in the final years of high school- not a sickeningly sweet or unrealistic anime high school, but one that feels a bit more like a regular average school where people might drop out or get into trouble or have family problems, etcetera). It is exceptionally easy reading- it's classified as a young adult novel, but it has a feel of maturity to it. I think the writer has done a lot of reflection, about people and things in general. After you have read a chapter or two of it, you will find it hard to put down- it tells an extremely clever fractured narrative of a mystery told from different view points- to amazing success! The anime- which is a kind of sequel to the book- continues this wonderfully fractured, quick-fire narrative style; and playing detective with it keeps it engaging.
The story leaves the reader with some good questions. Who really saved the world? Was it the people with special powers, or the normal, every day people who didn't think they had any power? Is the world really saved at all? Read/watch Boogiepop; give it a real chance and you will find out. Don't be put off by the fact that Boogiepop
looks derrivative- the gothy settings, the high school world, the phrase "supernatural horror"... Boogiepop will come to represent itself meaningfully, that is just it's disguise.
Black Jack
Black Jack in both manga and anime forms is quite the unique concept and a real success. If you don't care to see graphic medical procedures (i.e. you are squeemish) you may not care for it, but if not you are in for a wonderful treat; a fascinating collection of anthology stories. Avoid the movie version of the anime for now (it was a little dull), stick to the mangas and the 10-part OAV (both quite different). The manga is coming out in full now, thanks to Vertical publishing. Once you get past the graphic and disturbing first episode of the OAV, the episodes after are much more palatable and intriguing, and each tells a different story. Dr. Black Jack is a world famous surgeon who operates in back rooms, unofficial and unlicensed. He is a stoic and fair man who is happy to let people misjudge him for a devil in order to further his cause. He does not believe in how the medical system operates, and there is a strong sentiment against social injustice in the stories- though it is often executed in the most unusual of ways. He is a kind of medical Robin Hood in a sense, though his battle is often more fought by way of social deviance and finding a way to help people 'despite the system'. If you want to see really unexpected, yet mature things in anime/manga, by all means Black Jack is an excellent thing to get into. It is also the work closest to the heart of "father of manga" Osamu Tezuka, who also trained to be a doctor but never practiced due to his manga career.
Patlabor series
If you want to sample a good anime comedy enjoyable to a larger age range than average, I recommend this series a lot. Not every single episode is absolutely perfect, but when it delivers Patlabor really knows about people, about character development, and it has a warm and quirky soul. It has a varried cast of characters that might appear one-note at first, but go on get explored well over time. Patlabor will make you smile
and not merely talk down to you. There is a kind of wisdom even through the sillier parts. You'll love some of the characters over time. Start out with the original
7-part OAV series though- this one can be treated as a stand-alone, with the TV version expanding upon it. The first episode is gentle, but after that it's on fire with some really clever, fun stuff. Once you get the uniquely Japanese humour (often somewhat dead-pan), it'll be a hit. Even the strange or surreal elements are quite likeable. As an added bonus, Mamoru Oshii also directed much of this gem too. In fact half the time this is basically the same core creative team as the original Ghost in the Shell film- Oshii for direction, Kazunori Ito for writing, and Kenji Kawai for music.
I hope this list helps! It's not exhaustive, but it's my best picks all round. I tried to pick more intellectually-oriented things. I left out a few other things that should be on the list, but for lack of not wanting to go on about them I left them off:
Jin-Roh, Tenshi no Tamago, Serial Experiments Lain...
Other? A minor appendix ...
Have you ever seen
Watership Down? Although it's an English animated film, I really think it was very good too (more of a children's film, yet strangely filled with death and a rather brutal view of nature)...