2008's Flower, Sun & Rain for the Nintendo DS is such a cool little game. You play as Sumio Mondo, and he's a searcher. Basically, he's a guy you contract out when you need to find something--lost persons, things, etc. Basically a hide and seek detective. When the game starts off, Sumio is contracted out to the Hotel Flower Sun & Rain on a tropical island called Lospass to track down a bomb. This bomb has been hidden somewhere on the island, and the terrorist will use it to blow up a plane if you can't find it. What ensues is one of the most surreal, dreamlike video games I've ever experienced. During this adventure, you will fail at your mission some-17 times, be shot and killed, get made fun of by almost all of the characters, and interact with a pink crocodile named Christina who may or may not be god.
The gameplay itself is tedious, you walk everywhere on this big expansive island with a slow walking speed (you gain a run button later on, long after you'd have finished the game). The puzzles along the way are extremely obtuse, and include riddles, philosophical questions and highschool-level math. A lot of players interpret the meaning of this play style as a de-construction of playing a video game, or as the game hating you (a la Takeshi's Challenge). I don't think it's either of these though, I think the game is trying to convey an emotion less than fun. I see this game as a reflection of the impostor syndrome. You walk around this almost unrecognizable island and interact with people who have lived their whole lives there in one way or another, you being one of the only outsiders. Every character seems to really have their act together, while it becomes evident that Mondo is only faking his cool guy persona. Hell, in the beginning, he even addresses the player and says that if you can't figure a puzzle out, just to guess and eventually you'll get it! As the player, you're dropped into this nonsensical story with no idea of what's going on, and can only come to understand it through bits and pieces of things made clear. It's the ultimate crystalization of how it feels to be the new kid in town, the new guy on the job, etc. It's a game that I feel understands me, and that's not something I can say about most games out there. It might just be my favorite of all time!
Oh also the musicis totally rad!