"Working Class Hero" (John Lennon)

"Working Class Hero" from the raw/honest/anti-pop John Lennon/Plastic Ono Band (1970) may well be the most personal song that John Lennon ever wrote.  In fact, its spare Dylan-esque guitar and lo-fi production make it feel more like eavesdropping on a private session with his psychoanalyst than a song meant for public consumption.
Lyrically, he's questioning conformity and the status quo while sardonically looking at his own lot in life as a "working class hero."  It's clear that he sees himself as anything but a hero.
Whether you agree with the sentiment or not, you can't deny the man is telling the truth as he sees it, which is what makes it so compelling and timeless.