The Ultimate Smart iTunes Playlist

If you’re like me, you never listen to the radio because you’re very particular about the music you hear. Thankfully, this is the age of the iPod, when someone can carry their entire music library in their pocket, and you don’t have to worry about hearing a song you don’t like.

However, that doesn’t mean you’re always in the mood for certain songs. And if you have lots of single songs or old classics in your music collection, listening to them means you have to search for them. Just turning on the shuffle option in iTunes doesn’t cut it, because it’s a little too random; a song will be chosen regardless of whether you just heard it an hour ago or a year ago, and regardless of how much you like it.

really smart iTunes playlists

The solution is a smart iTunes playlist: a playlist that will not only have a mix of new music and old classics, it’ll adjust according to your tastes. That means you won’t need to interact in selecting or skipping songs, and a song won’t play over and over again, unless you want it to.

Another advantage of a smart playlist is that you can put on some music quickly, without having to decide what you feel like. If you tend to get focused on projects for hours at a time, it’s nice to not have to constantly be choosing the music to play in the background. And whether you’re taking a 5-minute walk to the grocery store, or a 5-hour drive out of town, a smart iTunes playlist will fill the time with music perfectly.

Here’s how I do it.

Organize by rating

The first thing you need to do is rate the songs in your library. You don’t need to rate all of them, but the more you have rated, the more will be in rotation in your smart playlist. Here’s my rating system:

  • 1 Star — These are songs I don’t like; usually part of an album, which is how they found their way into my collection. Rating a song with one star is more of a way of noting that I’ll probably delete it from my library eventually.
  • 2 Stars — These are usually transition pieces in an album, but important pieces nonetheless because the album can be disjarred and unpleasant without these tracks. In other words, songs you want to keep but only want to hear in the context of other songs. Examples are Parabol by Tool (which is followed by Parabola), or Interlude off Absolution by Muse, which fades into Hysteria.
  • 3 Stars — This is the meat of your smart playlist. Also considered songs you wouldn’t mind hearing a few times a year.
  • 4 Stars — These are the songs that stand out as being a better than the rest. Songs you wouldn’t mind hearing more often, but still ones that you may get tired of.
  • 5 Stars — Songs you don’t mind hearing over and over again, and whatever the situation or mood.
Note: these estimations are based on the size of my music collection. If your library only has 8 hours of music and you listen to it every day, you can’t expect to not hear a song more than a few times a year.

Protip: iTunes ratings are stored in your iTunes file, NOT in the audio files themselves. When making backups of your hard drive, make sure you backup your iTunes libary files too, or you may lose all your ratings if your hard drive dies.

Create your playlists

The smart playlist — which I like to call the -station — is actually a combination of four other playlists. These playlists interact with each other to keep your tunes going according to your tastes.

Note: It’s important that all playlists are ordered by number (the leftmost column), and not artist or album. They should also be set to “Match all of the following rules”, the -station being the only exception, which should be set to “Match any of the following rules”. I also keep live updating on all playlists so a song will remove itself from the rotation automatically once it’s played, or if you decide to change the rating on a song.

The Core

the core playlist

The -core is the collection of everything you want in your smart playlist, regardless of rating. You could look at it as a way of filtering out anything you wouldn’t normally want to hear, such as voice memos, TV shows, audiobooks, etc. And if you’re like me and need to be in a certain mood for genres like musicals and ambient, you can filters those out too.

Another way of doing this is to only include the genres you want to hear, instead of excluding the ones you don’t. So if you generally only like listening to electronic music but have a bunch of other genres in your collection as well, you can have “Genre contains dubstep, genre contains drum and bass, genre contains techno…”, etc.

The Infuser

the infuser playlist

The -infuser filters through all the songs in the -core playlist above for anything rated 3-stars. And it’s selecting the biggest chunk of music at 500 songs, so it makes up the bulk of the mix.

The Sprinkler

the sprinkler playlist

The -sprinkler will add in songs that stand out from the rest, rated at 4-stars. The setting for “Last played is not in the last 14 days” means you won’t have heard them in the last two weeks.

The Sprinkler+

the sprinkler+ playlist

The -sprinkler+ will add in any 5-star songs you have, regardless of when you last heard them.

The Station

the core playlist

And finally, the -station takes songs at random from the three playlists you just created for your customized mix.

Protip: You can add a hyphen at the beginning of the playlists in your radio station to keep them organized together.

Extra: Bonus playlists

unrated songs

Unrated: You can make a handy “Unrated” playlist to help with the process of sorting through your songs. When you have over 10 days of continuous music, it can take a lot of time to rate each one, even if you already know how you feel about a song. This is especially helpful if you add a bunch of new music to your library and forget to rate them, because it can then all be found in one place. As soon as a song is rated, it will add itself to the rotation.

favourite songs

Favourites: This playlist is simply any song rated 4 or 5-stars. I like to put this on as a pick-me up in the mornings or when I need an energy boost.

Play station

Once you have some songs rated and your playlists going, all you need to do is play the -station and let it take care of the rest. I choose not to enable shuffle, because I may decide to listen to something like a voice memo and then resume where I left off.

If you have your music synced with your iPod or iPhone and you play the -station from both there and your computer, it’s a good idea to sync up every now and then to update both on which songs have played. I usually go a week between syncs, so I fill my -station with a week’s worth of music.


As your music collection expands, your ratings and tastes may change too, so you’ll need to fine-tune your smart playlist every now and then.

Every person listens to music differently too, and many of these settings are very subjective. For example if you find your -station has too many 3-star songs and you haven’t heard any 5-star in a while, lower the number of songs from 500 song limit in the -core playlist. Or if you find you’re hearing your 4-star songs too frequently, increase the date range for when it was last played in the -infuser playlist.


Much of this article is based on this fantastic post by Adam Knight, and tweaked for my own geeky (and probably OCD) purposes, so much thanks goes to him.


  1. Would like to rotate the following:
    1. Playlist 1
    2. Playlist 2
    3. Playlist 2
    4. Playlist 2
    repeat until 100 songs have been scheduled.
    Playlist 1 is vocals
    Playlist 2 is instrumentals
    Want to play 1 vocal, then 3 instrumentals, then repeat

    Any ideas?

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