I asked this question because I was listening to an album recently that I have had since I was in 5th grade or so, one of my long-time favorites. And I only realized recently that it tells the story of my life in a way that I couldn’t have understood when I first listened to it. It’s far too embarrassing to reveal, however. ROFL. Suffice to say it helped me realize that I am a feminine mostly gay guy, haha.
Less embarrassing albums would be “Soundsystem” or “Evolver” by 311.
But as for books, I’d have to say The Perks of Being a Wallflower might be it. I grew up with that book (yes, yes, I’m a youngun), I have turned to it for solace many times, and each time I’ve re-read it, it has taught me something new about myself. The first few times I read it, I wasn’t even able to understand that the main character had been abused, because I did not know that about myself at the time.