How-To: Rediscover Your iTunes Music

If you have hundreds or even thousands of songs in your iTunes library, then it’s more than likely there are some songs which you’ve forgotten you even own — you can’t listen to every single one at the same time, after all.

By using iTunes’ Smart Playlist feature, however, you can create a playlist of songs which you haven’t listened to in a while. You can get iTunes to look through your music collection, work out which songs you haven’t listened to in a while, then present them all in a list for you.

  1. Create a new Smart Playlist by going File ? New Smart Playlist. Alternatively, if you hold ?, the + button at the bottom of the window will change to a gear icon. Click this to create a Smart Playlist a bit quicker.
  2. Set up a rule using the Last Played option. Change the second option to ‘is not in the last’, and the text box on the right will change into a smaller text box and another dropdown list.
  3. Enter a period of time using the options on the right. The amount of time you use is totally up to you, although I recommend a shorter amount of time for small iTunes libraries. To give you a sense of perspective, I chose 3 months for a 165 song library, and the playlist ended up only containing 8 songs.
  4. Make sure to keep the ‘Live updating’ box checked, otherwise your playlist won’t update with other songs that match the search parameter after the playlist is created.
  5. When you click OK, the playlist will be created and populated with songs that match you criteria you specified. The name of the playlist will be highlighted, ready for you to type in a custom name for it.

As long as you kept the Live updating option turned on, iTunes will automatically add and remove songs from the playlist as its data changes. This means that you’ll always be able to listen to something you haven’t heard in a while! Just remember to choose a sensible length of time for the playlist; too short, and you’ll end up with a massive playlist that you won’t be able to listen to all of before it changes. Too long and there’ll only be a few songs in there.

There is, however, one thing which will mess up your playlist. iTunes only updates the Last Played field if you listen to the whole song. Therefore if you skip a song you don’t like, it won’t be counted as a play and could ultimately end up in your playlist. To combat this problem, all it takes is one extra rule in your playlist.

If you’ve already created the playlist, you can right-click and choose Edit Smart Playlist to add the rule using the same window from before.

  1. Add a new rule by clicking the round + button to the right of the first rule.
  2. Change the first option to Skip Count and the middle option to ‘is less than’, then type a small number such as 2 or 3. This accounts for any accidental skips you may have done.
  3. Click OK and any songs with a skip count higher than the number you chose will be removed from the playlist, keeping only the ones you like in there.

Of course, you may have changed your mind about songs you didn’t like 3 months ago. For this reason, I choose not to implement this extra rule into my playlist.