So I realized I should make one for future reference, so I can just link people. I thought I had one but I can't find it. Note that because I read a lot, things that are written for genre savvy people obviously have an advantage here, because I get the jokes and it's great to see things that are fresh.
Anime/Manga -
Here is Greenwood/Koko wa Greenwood: A character-driven slice-of-life, with great, competent characters being put into situations from school festivals to encounters with chocolate alien androids (that won first place in the art contest!). Written on the awesome kind of crack, embodying the random serendipity of life with lots of extra awesome and heartwarming. Nine-volume manga & OVA are licensed, there's also a live action. I read and watch this over and over.
This is also a fantastic manga for genre savvy people with a sense of humor, even if you're not normally a Clamp fan.
Record of a Fallen Vampire: Nine-volume manga by the author of Spiral. Incredible plot twists, deep characters and a heart-wrenching great tragedy. Seriously, normally I don't care about spoilers, but this actually made my jaw drop. The art gets better after the first volume. Other great dark fantasy shojo/josei manga are Vampire Princess Miyu (manga, OVA, anime: anime's not as good as the other versions) and Ayashi no Ceres, which by the author of Fushigi Yuugi except it doesn't suck. It's like she went, "So, they like melodrama? Let's really give the protagonist something to cry about."
Majin Tantei Nougami Neuro: Do not watch the anime, it butchers the female lead's character by making her a typical shonen weak female, and that really destroys the series because she's so important. A shonen manga series where the male supernatural lead gets weaker instead of stronger ad absurdum that really focuses on the female viewpoint character's development and levels in badass. Neuro is alien enough it's practically xenofiction: an amazingly original series that breaks so many genres and cliches I adore it.
Mega Man Megamix and Gigamix should be required reading for every fanfiction author. This is how it's done. Adorable, badass, thought-provoking (robots have been used as a race issue metaphor in sf since the beginning) and full of attention to detail and real love of the source material.
The Lucifer and Biscuit Hammer - How did I forget this one when I originally made the list? So, so fucking awesome. Just... just wow. So many powerful and amazing moments that just grab you by the heart, gut and mind, but it doesn't fall into the 'trying too hard' trap, either. "An adorable lunatic who wants to smash the world to bits, a shut-in who'll do whatever she says, and a talking lizard. These are our heroes."
Books -
Villians by Necessity by Eve Forward - Especially if you did Dungeons & Dragons, etc. at all.
The Coldfire Trilogy by C.S. Friedman
Almost everything by Roger Zelazny, although the first half of the Chronicles of Amber is relatively underwhelming.
Archer's Goon by Diana Wynne Jones - one of the fantasy greats, but this is her 'how we got here' mystery approach at its best.
The Phantom Tollbooth & Terry Pratchett - seriously, these are required reading.
James White's Sector General series. Kind of like House, except the complete opposite of misanthropic. An anti-war series that conveys its message by simply showing what happens when people aren't jerks. An antidote to stupid people and stupid preachy Broken Aesop works, to read when faith in universe needs restoring.
Video Games -
Shin Megami Tensei: The press turn icon system is murdering love. Nocturne was my first RPG, and sadly it set the bar incredibly high. I didn't encounter another as good for years. Until SMT: Devil Survivor came out. If you're a fan of mythology at all, the person who introduced me to this series called it a 'mythorgasm,' and that's a good description. Cosmic horror, too. You will learn a lot from these games. Including that if you don't think, you will die. Except for Strange Journey, it's about strategy, not grinding. If you like these, look into Shadow Hearts, a cosmic horror series that went towards the crack form of insanity over the trilogy.
Tales of the Abyss because Jade. And Luke. And... Great characters, who you will want to murder almost all of before it's over, and/or bury them in hugs. This thing will repeatedly stab you in the heart, and do it well. Hate or love them, it's impossible to be indifferent to these people. A fantastic tragedy, even better on second playthrough+ when you can see all the foreshadowing and know what's coming and how much it's going to hurt. Hard to believe Luke once had an n_n face...
Mana Khemia 1. Not 2, 1. Great battle system, incredible characters. Done by the same people as Ar Tonelico: Great choral music, the first game is incredibly uplifting. The second... has a few good characters. Avoid every part of the third except the soundtrack. The Atelier Iris trilogy is also good, except for Atelier Iris 1's Lita.
Dragon Quest: I actually do prefer this series to Final Fantasy. The best games are IV-VI, the Zenithia Trilogy (released on DS) and VII: 8&9 are really 'Square tries and fails to capture what made Dragon Quest great.' Being literally railroaded by an exposition fairy? That, that right there is fail. Before that, though, Dragon Quest V has a sequence that shows the potential of video games as a storytelling genre. The main character's father is in a dungeon with him, and he asks if the boy is alright and heals him after every fight. It shows the love there, and then what happense next...
Lunar: Eternal Blue is the game a lot of vastly inferior RPGs rip off for their plot elements. Silver Star had someone who is probably the first White Haired Prettyboy in gaming. About halfway through EB, I said to myself, "Why don't more RPGs do ____, because it is awesome," and then I realized that a lot of RPGs had tried to copy said plot point, but completely failed to recognize what made it so awesome in Eternal Blue. A video game that actually shows characters getting closer! And it has effects on both plot and gameplay instead of being a tacked-on romance! Have I mentioned that I love gameplay-story integration? Both from a history of gaming perspective, and to see a ton of JRPG tropes done right, this game shouldn't be missed. It's also a lot of fun to play, of course.
Film -
Speed Racer "The most expensive avant garde film ever made." Normally, film isn't something that occurs to me as an artistic genre, since it's inferior to most other methods of conveying story and meaning. Since I can't read most facial expressions and body language, the subtleties of acting are lost on me, and since that's really the one advantage it has as a narrative form over books and animated things like games? Those others are better genres for me since they're not focusing on sending information along a channel I don't get. However, this movie? The color pallette, the commentary on the artist's experience by putting it in terms of 'low-brow' things like car racing, the use of actual narrative techniques... This is the one film that made me go, "Wow, movies actually can be art."