I’ve been having so much fun with a new iTunes Smart Playlist for the past month that I’ve just got to share it. The basic premise is to relive my entire musical history in rough chronological segments, with the goal of drifting through the highlights of the various eras of my musical life. Contemporaneous songs are grouped and played near each other, creating a nostalgic soundtrack to your life.

It’s proving to be a fun trip down memory lane as I associate particular songs with particular moments, like that 10th Grade state science fair trip (powered by grunge supergroup Mad Season), Christmas vacations, the first mp3 I ever downloaded, that first year of college (where my early pop-rock leanings begin to mix with my discovery of electronic music), that first Stereolab track and other sundry milestones.

As I’ve been working my way through the playlist for about a month, each day ha brought great tunes and great memories.

Before we get going, some initial statements about the playlist though:

• For best effect, you should have a fairly significant musical history. Mine stretches back seventeen years and just going through “the best” songs it’s taken me about a month to listen through the first six of them. The slowness is part of the journey for me though.
• Chances are, if you have a long music history, you also have a rather large library. Part of the fun that I’m having with this project is the anticipation as I wonder what song will be played next. So, while a large library isn’t necessary for this project, it will be more fun if you have a large pool to draw from.
• I keep bringing it up, but yes, this works best when the songs in your iTunes Library have the proper Date Added: the date you actually acquired the music, not just the date you added it to your iTunes Library. It’s the backbone of the playlist, really. If you’ve been building your iTunes Library since it came out in 2001, you should be good. If you’ve been collecting music longer than iTunes has been around, see how to back-date your songs. It’s tedious, but worth it.
• A considerable portion of the songs in your library should be rated. The goal of this playlist is not to listen to every song in your library, but only your favorites from past to present. The star rating is how we filter all the best tunes.

That all said, how do we create this wondrous playlist? It’s actually a very simple couple of selectors.

Making the Smart Playlist

Start a new Smart Playlist and add the following criteria:

click to enlarge

My Rating: 5 stars
This makes sure only your favorite songs enter the playlist.

Last Played is Before {today’s date}
This selector initializes the playlist. Any song played before this date is eligible for inclusion. And songs are automatically removed from the playlist after you listen to them.

(Optional) Playlist is masterPlaylist
I use a master playlist to make sure my tunes are on the up and up. It filters my library so that only songs that are properly tagged, with correct date added, etc are included in other playlists. If you don’t have or want a master playlist, you can leave this selector out.

Finally,
Limit to XX items selected by Least Recently Added
This is what really makes the Smart Playlist work. The number you use for XX really depends on the size of your library and how large a “slice of history” you want to listen to at any given moment. I keep mine between 50 (when I’m listening in iTunes) and 100 (when I’m out with my iPod for the day). The Least Recently Added selector adds the earliest songs (according to Date Added) to the playlist and automatically replaces played songs with the next earliest ones.

Using the Playlist

The most effective way to use this playlist is via iTunes’ Party Shuffle Up Next feature (Party Shuffle is no longer part of the latest versions of iTunes). What I like about this method is that as songs are removed and replaced from your nostalgia playlist, the new songs become immediately available to Upnext, allowing for some really smooth musical transitions. The downside is that you’re chained to iTunes for all your listening.

But you can take that playlist on the road via iPod (or iPhone). It works just like any other playlist. Keep in mind though, that for the true “river of time” experience, try not to listen to the entire playlist in a single sitting when mobile. This has the effect of creating a hard break in the listening by completely clearing out all the oldest unplayed tunes, then replacing them with the next batch of songs. It divides the experience into chunks rather than the “smooth river” that I find so appealing. My solution is to listen to, at most, half the playlist during any given session. That way, when go to update the playlist, the new songs are intermingled with the unplayed ones.

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Well there it is, the most fun I’ve had with a playlist in quite a long time. Hopefully, your nostalgic adventure will be as rewarding as mine has been.