One of my favorite all time movies is About A Boy, which is a movie that came out around this time of me being 14 years old. The entire soundtrack is done by Badly Drawn Boy, who has remained one of my favorite artists. I don't listen to him all that much but when I do, I'm naturally transported back to certain memories.
"The Hour of the Bewilderbeast" is a great album that reminds me of the winter of my freshman year in high school. The song "Everybody Stalking" reminds me of having my 'heart broken' the first time by some boy that lived over by Hwy 36 and had a crazy family life. He didn't go to my high school and I was so 'in like' with him, his green hair (or was it pink? i don't remember.) his Weezer obsession and his crazy stories of having a father who died of a heroin overdose. Many nights talking on AIM into the wee morning hours and I'd always listen to Badly Drawn Boy. He told me weeks later to basically fuck off (in a nice way, i think, i don't remember) and I was devastated. It was that whole new experience of what a 'heart break' felt like. That hole in the stomach, sinking rejected feeling we all know by now but the first time is always the weirdest. At least I had a cool soundtrack.