Smart Playlists on the iPod

As pretty an object as an iPod is, it’s also a lot smarter than the music players that people have used for years and years. From the 78’s, 45’s, and 33’s to the 8-track, the cassette, and the CD, most people have listened to recorded music the same way – cue up recording, listen from start to end, cue up second recording, lather, rinse, and repeat, ad nauseum. The only notable change was when CD players, like my durable old 1988 Sony Discman, could play the tracks on a single disc in random order. As kids, we made mix tapes with such enthusiasm because it seemed so novel to be able to assemble music as we wished and not simply listen in the order dictated by albums. Long before I was Time’s Person of the Year, I was busily mashing up music – except that was more than 15 years before those terms meant anything. The desire to “control our media” is a fashionable way to describe an urge that people have felt as long as there have been media to control, I suppose.

The mix tapes and CDs that I made years ago were great – fun to make, fun to listen to, and fun to give to others. Yet they were static. In terms of capturing a time and place that was great – but in terms of being endlessly different, well, we didn’t dream that big. But with iTunes and an iPod, playlists can be considerably more powerful and clever. There are plenty of tutorials all over the web, and there is one site – – that’s especially helpful. Rather than offer any general comments, I thought I might share my favorite playlist.

Before starting, I have to say this list relies mightily on ratings, so if you wish to borrow from it, you’ll either need rated tunes or be willing to take the time to rate your library. This is a dull task that is well worth the time and effort it takes. iTunes offers a 5-star system, and while there are people who use various hacks to implement half-stars, I have chosen to stick with the stock 5-stars so far. In my scheme, 1 star is reserved for music so awful it should be dumped out of iTunes, 2 stars are for music I may not know well or just don’t like very much, 3 stars are for songs I like okay, 4 stars are for songs I really enjoy very much, and 5 stars are for songs that I love. With this starting point, I tried to create a playlist that would behave like a perfect radio station. Maybe not truly perfect, because it’s not stocked with a cute blond DJ, but one that would play the things I love often, and the things I like a lot frequently, and then array around that music an interesting mix of things that seemed a little less familiar, yet related to the music I know I enjoy.

To accomplish this in iTunes, I use a capability that did not used to be part of the program and offers great power – dependencies among playlists. When married to iTunes’s record of when each track was last played, I can begin to assemble a very powerful instrument. To wit:

  • Four playlists that consist of 2-star songs I have not heard in eight weeks, 3-star songs I have not heard in six weeks, 4-star songs I have not heard in four weeks, and 5-star songs I have not heard in two weeks.
  • Next, for flavor, I add in the last 15 songs I have downloaded from the iTunes store. I chose 15 as the download cards I have been given as gifts come in $15 denominations, so I think of 15 songs as a basic block of iTunes music. These are selected by a filter on file type sorted by most recently added.
  • I also add in the most recent 15 songs I have ripped from my own CDs. Fifteen works here for two reasons – it balances against the downloaded music and it also manages to capture about an album’s worth of tracks, as I usually rip whole albums at a time. These are also selected by a file-type filter and sorted by most recently added.
  • I then add in my 15 least listened to 5-star tracks, which is a good way to make sure that recent additions to this league are in rotation while ensuring shuffle play doesn’t overlook any tracks for too long.
  • I then create a playlist that grabs the seven playlists from the previous entries and removes any podcasts, audiobooks, holiday music, or other nonsense that may have crept in here (who else remembers hearing the chittering nonsense of an unrequested Griffin iTrip tuning track?).

I name this resulting mass of music WRAN, and it’s what I cue up in the car each morning and listen to all day long at my desk. From the several thousand tracks in my iTunes library, it pulls between 1,000 and 1,500 at a time, and I listen to somewhere between 100 and 125 songs on a given day. Now, without paying a dime to the FCC, I get to listen to music that feels like it was selected by a radio program director with tastes identical to mine. I never hear the same tracks in the same order, and each day is a different array of music. If I don’t like something, I skip it, and that skip counts against the track in iTunes. One day I plan to use that information as a way of refining my playlists, but I don’t have enough skip history to make that worthwhile yet.

Anyway, more than you wanted to know. has many suggestions for similar ideas, some more complicated, and some more obvious. I encourage you to browse through their posts and then build a new playlist that will delight you. You’ll wind up loving your iPod even more than you do now. Really.


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