Kanye West - Heartless

Mr West has being getting a lot of negative publicity the last few days and rightfully so. Though this is a great take on why despite his unrivaled ability to behave like a dick, he's one of the most important artists of his generation. For my money, if your talking about people who have combined commercial success with a willingness to push artistic boundaries over the last decade you've got Jack White, Kanye West and that's pretty much it.
This song is just fucking amazing. That whole album is mental, but here's where it all comes together. He takes autotune, which is reviled for sucking the emotion out of singers voices and over uses it to the point it starts to make a desperate sort of sense. One thing you can never accuse the man of is a lack of emotion. This song also highlights that for all Kanye's monstrous self obsession, it is undercut with an unflinching honesty.
'Heartless' is all about how he cannot believe that this woman would treat him badly, cause, you know he's Kanye. But he still manages to fess up in the song that he fooled around on her. He may well be self obsessed to the point of delusion but the fact he can't conceal anything makes him strangely endearing.