Turn iTunes Up to 11
Posted 07/27/2010 at 2:46pm
| by Craig Grannell
Smarter iTunes Playlists
Power up your iTunes playlists with minimal effort
Technology moves pretty fast. People used to spend entire Saturdays happily compiling a “mix tape” by carefully recording favorite tracks on a cheap cassette deck, but once digital music hit its stride, such endeavors were seen as a startling waste of time. With a music collection sitting on your hard drive, mixes could be made quickly thanks to the magic of drag and drop.

Select any track in your library, click the Start Genius button, and presto, you have a unique playlist!
iTunes easily creates static playlists, and always has. Click the invitingly large Plus button at the lower left of the main iTunes window (or go to File > New Playlist), name your playlist, and then drag in tracks from your library. Tracks can be reordered, and you can also drag songs from one playlist to another; note that the track also remains in the playlist it was dragged from--it isn’t removed. It’s also worth noting, in case you’re concerned, that playlists contain “shortcuts” to the original tracks. Delete a playlist or an item from a playlist, and the original track remains in your library.
An Automated Approach
With iTunes 8, Apple introduced its Genius technology, which tries to predict listening habits based on the collections of millions of iTunes users. This lets you create a playlist of tracks based on a favorite song. Select a track in your library, then click Start Genius at the bottom right of the iTunes window (or Control-click and select Start Genius). iTunes will create a 25-item playlist containing that track and similar songs. By using the controls above the playlist, you can extend it to 50, 75, or 100 items; refresh it; or save it.
Saved Genius playlists appear in the sidebar’s Genius section, but Genius Mixes are included by default. Select this to access mixes that are genre-based, randomized, and sealed. You can’t access Genius Mixes to see which tracks are up next, nor can you view a full list of albums and artists, but they’re still a handy “personalized radio” for those days when even starting up a Genius playlist seems a bit too much like hard work.
Smart Playlists
Introduced in iTunes 3, smart playlists are dynamic; they’re based on user-defined criteria. This same idea is used elsewhere on your Mac--smart folders in the Finder, smart mailboxes in Mail--although the iTunes implementation is the most advanced and flexible at the time of this writing.

File > New Playlist Folder adds a handy folder to the sidebar, into which you can drop static and smart playlists for easy access.
To create a new smart playlist, go to File > New Smart Playlist or use the keyboard shortcut Command-Option-N. This brings up the Smart Playlist dialog. To create a basic smart playlist, leave all the settings alone, but add your favorite artist to the empty field, and then click OK. Your new playlist will be added to the sidebar and highlighted. In the main iTunes view area, you should see a list of tracks from your specified artist.

An example of a nested playlist--these can be as simple or as complex as you like, so go crazy!
Since they’re dynamic, smart playlists can be updated with new settings. Select your playlist and go to File > Edit Smart Playlist (or Control- or right-click it and select Edit Smart Playlist). Click the Plus button to add a new rule. The left-most menu includes many criteria you can pick from. Add as many rules as you like, and define specific values for them. The Match menu lets you choose whether the playlist includes tracks determined by all of the rules or any of them. The former could be used to create a playlist of tracks by your favorite band, not including that one lame album (Album > is not > [album name]), and only from the 1990s onwards (Year > is greater than > 1989). To remove a rule, click the adjacent Minus button, although be aware there’s no undo.
Advanced Rules
The Smart Playlist dialog has a few options that can further refine your playlists. The Limit checkbox enables you to set a specific track count and also a selection criterion (random, recently played, and so on). If the Live Updating box is checked, relevant tracks subsequently added to iTunes will be added to the playlist without you having to do anything.
With iTunes 9, Apple finally added a change that smart-playlist gurus had demanded for years: nested playlists. Before iTunes 9, complex playlists of the form “A and (B or C)” required you to make the “B or C” playlist first and then a second playlist to work with its output. Now, however, you can use the “…” (ellipses) button to create nested rule groups and therefore playlists with complex logic.
If this concept sounds tricky in the abstract, here’s a practical application for nested smart playlists. Say you want to create a playlist comprising tracks from 10 of your favorite bands, only using songs rated above four stars and that have not been played in over a month. Previously, this would have required two playlists, because the bands are an “any” match, whereas the other rules are an “all” match. With iTunes 9, you set up a single match-all smart playlist with the time and ratings rules, and nest a match-any set that deals with the band names. An example is shown above, but the sky really is the limit with smart playlists, and once you’ve set a few up, you can let iTunes do all the hard work of adding tracks. It’s a long way from waiting for a cassette to run out of tape!
Base Your Playlists on Ratings

This simple smart playlist finds favorite tracks you haven’t heard recently.
The best smart playlists are often the simple ones: If you rate your tracks, create a smart playlist where track ratings are greater than 3 and call it “4+ tracks.” For your very best tracks, create a smart playlist with tracks rated 5. If you’re always forgetting what music you’ve added over the past couple of months, create a smart playlist with the rule: Date Added > is in the last > 60 days, and where Media Kind is Music. Create a similar playlist, but change 60 days to 12 months to include songs you’ve added over the past year. Or if you’d like to unearth lost favorites, create a playlist called “4+ neglecteds” and set rules based around track ratings (Rating > is greater than > ***) and when the tracks were last played (Last Played > is not in the last > 30 days).
Target Your iPods

Unless you have a 120GB iPod classic, your Apple music player has a relatively limited capacity. That’s fine if your music collection is small, but if it isn’t, you can always create a playlist with nested rules to fill it full of favorite tracks.
In the example below, the Time rule dispenses with very short (under 40 seconds) and very long tracks (over 5 minutes), classical music, and anything with a very high bit rate (although you can automatically “downsample” audio during syncing in iTunes 9.1). The Media Kind rule restricts the playlist to music, filtering out spoken audio and the like.

If you’ve got an iPod shuffle, fill it with highly rated, short-ish tracks.
Our nested rules follow this logic: Tracks are only added to the playlist if they’re rated over 3--unless they’ve been added within the previous 14 days and don’t have a rating of 1. This means that you always get recent tracks (including all unrated ones) unless you’ve already decided to mark them as rubbish, but older tracks are filtered by your rating.
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