How has this one not come up yet as a classic?
Paranoia Agent
Trigger warnings on this one. Dark, surreal, and, I feel, becoming a more and more accurate representation of the world we live in. It starts as a mystery, moves into psychological thriller, then becomes a supernatural metaphor for modern society and escapism. It has a decent sized cast with interesting characters, a nice mystery, good animation, and a good pay-off at the end. Oh, and it was created by the late Satoshi Kon, who also directed Tokyo Godfathers and Paprika.
It starts off simple enough. The main character is attacked by a boy with roller skates and a golden bat. Soon other people are also getting attacked by this hoodlum. However, he only seems to attack people that are under a lot of pressure and can't cope.
Is the fast pace of society getting a little too fast for you? Are the pressures of living overwhelming you? Is the 24-hour Newscycle driving you mad? Is the other side on the political spectrum making you hate humanity? Are your personal failings weighing you down?
Do you just need to escape?
Lil Slugger wants to help.
Trailer: https://www.youtube.com/watch?v=PzeddeDLouw