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. This is awe­some! I’m going to do this when get home.

    My library is in des­per­ate need of clean-up too, so I’ll have to devote some time to that. I had shuf­fle on while I was play­ing Torchlight this week­end and some real crap came up.

    • You could sim­plify –core to just use “Media Kind” is “Music”.

      • You’re right, thanks for the tip…I’ve updated the screenshot.

  2. I’ve always wanted this but have never got­ten past the stage of rat­ing the songs because… well I move on to other things that inter­est me more than orga­niz­ing dig­i­tal files.

    Maybe I should get Brent to do this for me. Whenever he sees that only half my tracks have art­work and the titles/artists aren’t all cap­i­tal­ized in the same fash­ion he takes my stuff and ‘fixes’ it for me.

    • But you only need to orga­nize them once and then they’re all clean and pretty! I guess it all comes down to priority…I’d clean my music files before I clean my bathroom.

      Glad to hear Brent is as much of a stick­ler about that stuff as me. That’s prob­a­bly be the only thing we have in common.

      • You actu­ally have more in com­mon than that. Let me think:

        –you both have musi­cal instru­ment play­ing as hob­bies
        –You are both into hav­ing a very neat and tidy house (I’m assum­ing this since your house has always been tidy when I was there)
        –you are both dudes

  3. Thanks for this post! I have never rated my songs because as I tend to be up, down, or in the mid­dle, I have about seven playlists that fol­low those and other cri­te­ria; never thought of doing it this way. I’m going to cull my lists soon and then clean it up with this.

    The sad part for me is that I now real­ize since I no longer com­mute, I rarely am able to lis­ten to more than a half hour of music at a stretch, every morn­ing, while play­ing with my grownup face­paints.…. that’s SO not enough music per day. I need to increase my quota.

    • I’ve noticed the same thing about chang­ing com­mutes. I used to have over an hour bus ride to work, so I used to lis­ten to albums that would last that long. And since I was stuck with­out any­thing else to do, that meant I had a lot more tol­er­ance for pro­gres­sive rock songs that go on for over 15 minutes.

  4. Wow, I’ve never thought to orga­nize a playlist this way! I usu­ally just go by a mood or a theme or just plain “songs for dri­ving” and end up with a ton of repeats.

    • I used to lis­ten to my music based purely on mood too. I had sev­eral playlists orga­nized as such, but even­tu­ally I found it much too tedious to sort my songs into each one cause it’s not some­thing you can do quickly and eas­ily when you’re on the go; with the star rat­ings, it’s some­thing you can do right on your iPhone or iPod.

      Eventually, I found the ulti­mate smart playlist to be good enough.

  5. Thanks for shar­ing this idea! I adjusted my core list to allow the Soundtrack genre and fil­ter out spe­cific tracks within that genre using the 2-star rat­ing. Some sound­track albums con­tain actual songs, not just the instru­men­tal back­ground music from a movie. “Austin Powers: International Man of Mystery” and “O Brother, Where Art Thou” con­tain songs that were pop­u­lar in their own right prior to the film, and the “Out of Africa” sound­track includes Mozart’s Clarinet Concerto in A Major, a piece which holds a 5-star rat­ing in my library!

  6. Can you write the fol­low­ing smartlist for me. I can’t seem to get it. I want two rules. One play higher rated songs more often. Play songs once a week. i look for­ward to your reply. Using Itunes for Mac OSX 10.4 ver­sion 6

  7. I do some­thing very sim­i­lar, except that I limit my unranked playlist to 25 songs picked at ran­dom. Gives me more incen­tive to do it when it’s only 25. Anyway, When I rate a song of course it goes away and a new one pops in, and the song would skip to the next song in queue. In iTunes 11, it stops the playlist now :(

  8. My library out­grew my 160gb ipod a year ago and I’ve been putting off find­ing a work around since then. Thanks for such a clear and excel­lent post.

  9. Hey there. Amazing arti­cle. I do exactly the same thing.

    What I rec­om­mend too is a list
    “Songs of the moment“
    ie. songs added in last 12m, lis­tened too over 5 times and rat­ing 4* or over.

    I love this playlist and picks up always good tunes.

  10. Hey Jeff — this is a great arti­cle! I had no idea that itunes has this kind of capa­bil­ity. You’ve basi­cally fig­ured out how to built your own rec­om­men­da­tion engine! I too have the shuf­fle woes where I feel like I skip 50 songs in a row and give up.

    One thing I won­der — is it easy to share these pre­built playlists between itunes users? I like to throw out­door par­ties and it would be cool to have dif­fer­ent friends stream to my sound sys­tem, and give me their pre­pro­grammed list if I like it.

  11. Hi Jeff, I love the sys­tem you have put in place. I do have one ques­tion for you, how do you deter­mine the rat­ing dis­tri­b­u­tion. What I mean is do you set your­self an amount (or per­cent­age) of 5 stars vs 4 stars vs 3 stars. I always end up hav­ing too much of one or the other either because I tend to overrate.

    • Hey Alex, I don’t have a ratio sys­tem to keep a bal­ance of 3 vs 4 vs 5 star rat­ings. If you feel like you’re end­ing up with too many of one type in your sta­tion, try adjust­ing the “Limit to X items” option for both the Sprinkler and Sprinkler+ playlists.

  12. Question for you…

    I like ran­dom­ness and don’t want to hear the same artist two times in a row and prefer­ably once every 5 songs.

    Do you have any idea to make the fol­low­ing rule: “artist not played in last 5 songs” ?


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