It’s the night before my first day of high school, and I’m feeling some feelings. Anxiety. Curiosity. Nostalgia for what I’ve left behind. Excitement for what’s to come. Just 12 hours from my first day in a brand-new school, I don’t know whether I should be scared shitless about diving into the deep end, or reveling in the anticipation of everything that comes with a new start. I know I might lose myself in the great big unknown I’m journeying into. But I also know that there’s opportunity for growth and reinvention and self-discovery waiting somewhere out there. And so, I’m staring down the first day of the rest of my life and trying to sort out the good from the bad. It’s enough to drive any 14-year-old boy mad. Thank goodness, then, for the soundtrack, which might just be the only thing keeping me sane.

I’m fond of saying that my favorite traditions are music-related traditions. I love marking different points of the year with different songs, or albums, or playlists. Holidays; anniversaries; seasonal shifts; specific runs or drives; daytrips to certain places. All these things, for me, can be tied to specific musical cues that become rituals or traditions. Every year when it gets warm enough for a windows-down car ride, for instance, I am, by personal law, required to take a drive with Jack’s Mannequin’s Everything in Transit playing very, very loud. It can’t be summer until I’ve done precisely that.

My favorite musical tradition of all time dates back to that Labor Day evening in 2005, right before I headed off to high school for the first time. I’ve always held that there is no melancholy quite like the melancholy of the last day of summer when you’re young. It’s a bit like the peculiar sadness of a Sunday evening, when you know that you have to head back to work or school the next day, but wish the fleeting freedom of the weekend could last a little longer. Except for that, in summertime, as a kid, the freedom does last a little longer – so long that it seems it might last forever. I’d felt that peculiar melancholy before – the mix of sadness at summer’s end and anticipation for the start of something new. But I’d never felt it quite as strongly as I did that day, when it seemed like I might be at the end of what constituted my true “childhood.” It felt momentous in a way, and it needed a soundtrack to capture what I was feeling: the end-of-summer ethos, the melancholy, the finality, the excitement. No one album felt fitting, so I made a playlist.