It's easy to set up playlists in iTunes, although it can be time consuming, particularly if you have a large library of songs (and who doesn't?).

You can use the handy Smart Playlist feature to make iTunes do most of the work for you. Don't let the word 'complex' scare you. In just a few minutes, with just a few clicks, you can create Smart Playlists based on one or two criteria, a long list of criteria, or anything in-between.

For example, you can create a Smart Playlist based that gathers all of the tracks by one of your favorite artists, all of the tracks by that artist to which you've assigned a 5-star rating, and all of the tracks by that artist in a particular genre, such as 'Rock.'

If you want to create a simple Smart Playlist, perhaps just to gather all of the songs by a particular artist, check out our 'How to Create a Simple Smart Playlist' guide.

Create a Complex Smart Playlist

1. To create a Smart Playlist, from the File menu, select New Smart Playlist, or New, Smart Playlist depending on the version of iTunes you are using.
2. The default Smart Playlist is based on a single rule, but you can add more rules as needed. There are more than three dozen criteria to choose from, as you'll see if you click the Artist dropdown menu. You can sort tracks by artist, album, compilation, category, genre, plays, and rating, among other possibilities. You can create Smart Playlists for any iTunes media, not just tracks, but we're going to focus on music.

1. After you make a selection from the Artist dropdown menu, make a selection from the 'contains' dropdown menu (contains, does not contain, is, is not, starts with, or ends with), then enter the appropriate search term in the blank field.
   For example, if you want to create a Smart Playlist that contains all of your Dave Matthews tracks, including tracks by the Dave Matthews Band, you might set up the following rule:
   

   
   Artist contains Dave Matthews
   

   Any track that has Dave Matthews in its name, such as Dave Matthews Band, will be added to the playlist. If you want the Smart Playlist to contain only your favorite Dave Matthews tunes, you might add a Rating rule:

   
   Rating is 5 stars
   

   You might also add a rule that the number of plays is greater than a certain number, such as 100. If you've played a track a number of times, chances are it's one of your favorites. So, you might add another rule:

   
   Plays is greater than 100
   

   With the following rule, you can also rule out iffy tracks that you generally skip:

   
   Last Skipped is in the last 30 days
   

   And to be sure that your playlist contains tracks but not videos, you might add this rule:

   
   Playlist is Music
   

   You can exclude things as well as add them. For example, if you don't want any Christmas tunes by Dave Matthews to be included in your Smart Playlist, you might add this rule:

   
   Genre is not Holiday
   

2. If you want the Smart Playlist to be automatically updated when you add matching tracks to your iTunes Library, put a check mark next to 'Live updating.' (This option is selected by default; you can uncheck it if you don't want the Smart Playlist to be updated automatically.)

There are thousands of possible Smart Playlist combinations, and it's easy to fine-tune a playlist to be just what you want.