I’m currently watching High Fidelity, the TV show, because I love the movie and the book, and precisely because of that, I never got around to watching the show for reasons of not wanting to ruin a good thing. But a friend recently recommended the show, and given that it’s half-hour episodes, I said why not. 

High Fidelity is a show about breakups — or more specifically, about one breakup — but it’s also a show about playlists and Top 5s.

And that got me thinking about my Top 5 breakup songs. 

A couple of years ago, I made a playlist after a particularly bad breakup. There are 44 songs on it. And at the risk of sounding hyperbolic, it was a healing experience making that playlist. And almost every time I listened to it at the time, I cried. 

A few years after that, I had another breakup, and I tried listening to the playlist again, and of course it does not work. The playlist was coupled to that particular breakup; that particular person. And instead of helping me connect with my feelings after the new breakup, it took me away from them.

Songs are tied to emotions, which are often tied to moments, which are tied to people. And once those things are entangled, it’s hard to disentangle them. The emotion can randomly bring up the song, which can then summon the person. Or the song can bring up the person which can then leave you, all of a sudden, drowning in the emotion.

So I don’t think there’s such a thing as a contextless breakup playlist. At least not for me. But because I have not made a breakup playlist since that last one, here are my 5 favourite songs from that playlist in no particular order: