Ever wonder what you were listening to three, four, five or even ten years ago? Or maybe you want to look back and wonder “have I really been listening to this album for that long?”.

Enter The Anniversary Playlist.

By setting two simple Date Added parameters in a Smart Playlist, you can make a self-updating playlist of all the music you were listening to a given number of years ago. It makes a great little time machine.

Here’s one to get you started: 5th Anniversary Tunes.

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No matter how far back you want to go, you only need the Date Added selectors and a little simple math.

First selector: Date added is in the last XX months
This criteria includes every song you’ve added to your iTunes library in a given number of months. Since we’re talking years here, we need to multiply the number years by 12 to get the number of months. 5 years = 60 months. But since we want to have a slice that’s slightly older than 5 years, we add 1. So all music that was added in the last 61 months is added to the playlist.

Second selector: Date added is not in the last (XX – 1) months
But we don’t really want our playlist to include all the music that’s been added in the past 61 months, so we use this criteria to exclude everything that’s newer than 5 years old. This leaves us looking at a window of exactly one month from 5 years ago. As each day passes, the window moves and older songs drop away and are replaced with the more recently added.

Looking at my library, I see a number of songs from March 2004. It seems that it’s now been five years since I discovered Elbow (which makes me wonder the aforementioned “has it really been that long?”) as well as filled out my Stereolab singles collection. Also, Tortoise needs a new album. It’s been five years since the last one.

To adjust the window, simply change the number of months back to look. One year ago would be 13 and 12 months, six would be 73 and 72, and so on.