S. F. Sorrow by The Pretty Things (1968)

Considered by some to be the first rock opera (and if not the first, certainly the best among the first few by a wide margin), the fourth studio album by London's The Pretty Things explores the full lifespan of a single character throughout the course of its thirteen tracks.

The initial idea for S.F. Sorrow and its story was inspired by "Cutting Up Sergeant Time", a short story by Phil May about a man fighting in the trenches of World War I. Once the idea was agreed upon, the story began to evolve from there.

According to the story found in the album's liner notes, the lead Sebastian F. Sorrow is born to parents who live in an ordinary factory town on a night when no star is to be seen. As a child he has a strong imagination and often dreams of the moon. As he comes of age he joins his father in the factory but the boom period is over, with many older workers now laid off. He falls in love with "the girl next door" but war is soon declared and out of a sense of duty, he enlists in the army. At the end of the years-long war he finds himself in the new country of "Amerik" and decides to move there, sending a balloon ticket to his girlfriend to come join him. However, just as the balloon arrives it explodes, taking the girl with it and plunging Sorrow into deep grief as he wanders the streets of New York City alone.

One day he is approached by Baron Saturday, wearing a black cloak and tall silk hat. He takes Sorrow's eyes and lifts him to the roofs of the city, where sparrows (prodded by Saturday) carry him on a journey through a hall of mirrors through which Sorrow sees fragments of his past life. At the end of the hall he walks up a spiral staircase to see "the most painful sight yet." Saturday then takes him to the Well of Destiny, after which he begins to search for new, spiritual values in life. However, as he wanders the streets once more he sees people who he believes will not be saved. As new values appear elusively out of reach and his madness slowly builds, it shuts out the light and only darkness remains.

So 60s it hurts, but it the best way imaginable.