2. Weezer - Pinkerton
https://www.youtube.com/watch?v=Iza2jJQb4iw When: 11th Grade Why: My friends are better looking than I am Number of relatives asking me about my college plans: All Boy howdy was this a rocky one to say the least. What began with an awkward hello in front of school and ended with me vomiting a crudely mixed ginger ale and vodka in a Chipotle bathroom can be summed up in one word: Pinkerton. Pinkerton is the second and most unique Weezer album. it was conceived after Rivers Cuomo (or Jason Bateman, who can really tell) entered both Harvard and a deep depression. He painted his walls black, read Madame Butterfly, and recorded the most heart-wrenching pure break-up album ever. Every trope of the romantic teenage boy is examined here: from the "married in my mind" disorder (which, to be fair, I totally suffer(ed) from at the time) to the pains of a long distance relationship. Pretty much every song on this album represents some element of the protagonist totally f**king up, and walking through those steps as I f**ked up my own quasi-relationship certainly prepared me for dark times ahead. Even the melodies resonate with the heartbroken: especially the delicate piano in "Across the Sea", to the hard rocking on "Why Bother". But what sinks in the most is the stunning accuracy of Cuomo's lyrics (it actually did "happen to me twice before"!). However anyone feels about their ex lover can be described by at least one of these songs. But the really messed up ones should go ahead and check out all of them.