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Let’s say you want to create a smart playlist in iTunes that will contain the 25 highest-rated Beatles or Bob Dylan songs that you haven’t heard in a while. That would be pretty cool, right? It’s not that simple, but it can be done. I’ll show you how.

The main roadblock you’re facing is that iTunes only gives you two ways of restricting / selecting songs. You can build a smart playlist based on songs that meet all of your criteria or one based on songs that meet any of your criteria. This any / all option really puts you in a corner. First I’ll explain why, and then I’ll show you how to fix it.

We want all the songs where the artist is Beatles, The and we want all the songs where the artist is Dylan, Bob. Fair enough. Create a “New Smart Playlist …” that looks like this:

The Problem

This will not work.

We’ve got it set to “Match all of the following rules.”

A song can’t have the Beatles and Bob as the artist; your “smart” playlist will always be empty.

So we have to change that to any instead of all. Now we’re in good shape. If we set it to any, this playlist will contain every song where the Beatles or Bob is the artist.

So far so good.

Now we want to only include the songs that are rated three stars or better. So we add a new rule:

(Saying we only want to include songs where “My Rating” is greater than two stars means that all the songs will have three or more stars.)

Unfortunately this will not work either.

If you build a playlist like this, you’re going to get every song that’s rated better than two stars (regardless of the artist), and every song that’s by the Beatles or Bob (regardless of the rating)!

That is not what we want.

But fear not. Hope is on the horizon. We can <drumroll> … nest playlists!

The Solution

Remove the “My Rating” rule, leave the “Limit” box unchecked, and save this playlist as “B&B-Total” or something like that.

Now create another “New Smart Playlist …” For this one you’re going to choose to “Match all of the following rules:” and your rules will be to select songs where “My Rating” is greater than two stars and Playlist is “B&B-Total”. Like so:

Now we’ve done it!

This playlist will give us the 25 songs that:

• are by the Beatles or by Bob Dylan
• are rated three stars or better
• and that we haven’t heard in the longest time

Exactly what we want!

If you have the latest version of iTunes, you can create folders of playlists, which is handy when you start building nested playlists like this. I have a folder named “Sources” and that’s where I put the base playlists. I’d be much happier if the folders translated to my iPod, but I’ll manage …

See also: Five Tips for Smarter Playlists

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