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:

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.