If I had to guess, I think I have listened to the Siamese Dream album by the Smashing Pumpkins more than any other album ever made.
Probably 5 years ago, I came across Billy Corgan's myspace profile. Ah, shut up. He had used the opportunity to post a link to a Livejournal account to which he was semi-secretly posting huge chapters of autobiographical writing. He started in early childhood and detailed year after year of strange, faltering, confusing experiences. Some of them were profoundly sad. He left off around the time that he was writing his first album. They weren't famous yet, and he was sleeping on a couch in a storage unit or something. He was still having his strange and sad experiences then, and I would guess that he still is now.