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iTunes started out as a smart, simple music player, but over the years, it’s evolved into one of Apple’s most important applications. Although it’s still used for managing and playing your music collection, iTunes now also stores apps, films, TV shows, podcasts, ringtones, and books--maybe “iStuff” would be a better name?--and of course, it’s the sole Apple-approved method for syncing content with iPods, iPhones, iPads, and Apple TVs.
But that doesn’t mean you should take it at face value. Like many of Apple’s applications, iTunes is multilayered. Underneath its simple, straightforward hood, it’s surprisingly feature-rich, offering many powerful configuration options. And it’s time to make that power work for you with our guide to tapping into iTunes’ lesser-known but highly useful features. We also delve into the add-ons that expand the iTunes experience, including the very best third-party applications and highly useful scripts. So fire up iTunes 9.1 or later (it’s currently at 9.2), and get ready to rock!
If iTunes were a rock band, it’d only play stadiums. Besides storing and managing your music, the application has to deal with video, books, apps, ringtones, and more. To Apple’s credit, iTunes remains pretty usable, and much of its complexity is kept hidden under the hood. But don’t forget about these useful features.

Uncheck any media types you don't want cluttering up your sidebar.
To change the default media types shown in the Library section of the sidebar, use the checkboxes in iTunes > Preferences > General. If any sources are grayed out in that menu, they’re probably disabled via parental controls. Those settings can be adjusted in the Parental section of the Preferences window.

Set the import format here.
By default, iTunes imports audio using the AAC Encoder set to 256kbps, which is how iTunes Store music is sold. AAC is fine for iPods, but if you use a non-Apple player, you might prefer MP3--head to iTunes > Preferences > General, and click Import Settings. If you’ve got tons of storage, Apple Lossless is the best encoder, and iTunes 9.1 and later can automatically convert songs to space-saving 128kbps AAC when you sync an iDevice (in the device’s settings pane).

Open sesame.
Although primarily designed as a single-window app, iTunes lets you open most sidebar components (Music and Connected Devices being exceptions) in their own windows by Control- or right-clicking and selecting “Open in New Window.” If you’ve got a large monitor, it can be handy, for example, to view your music library and the iTunes Store simultaneously.

Pump up the bass, yo!
The often-overlooked Equalizer (Window > Equalizer, or Command-Option-2) has sliders you can fiddle with to adjust the sound, along with presets in the drop-down menu. iTunes can save your custom settings if you choose Make Preset from the drop-down menu.

As List - Command-Option-3
As Grid - Command-Option-4
As Cover Flow - Command-Option-5
Show/Hide Column Browser - Command-B
Show Artwork Column - Command-G
Show Genius Sidebar - Command-Shift-G
Switch to/from Mini Player - Command-Shift-M
Pause - [Space]
Next - Command–right arrow
Previous - Command–left arrow
Eject - Command-E
Back - Command-[
Forward - Command-]
Home - Command-Shift-H
Next page: 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.
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.
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.
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!

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).

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.
Next page: The Best iTunes Add-Ons >>
iTunes gets even better with one (or all) of these apps as its backup singers

Once you set the preferences, the app stays in your menu bar.
Even if your library is modest, rating all your tracks can seem daunting. But a rated collection gives you more possibilities for smart playlists, and I Love Stars lets you rate as you go. The app sits in the menu bar and shows the currently playing track’s rating. To change the rating, click on the relevant star. Control-click to access the preferences and define systemwide keyboard shortcuts for rating tracks. I Love Stars can even alert you (optionally) when an unrated song is almost done playing.

Tinker with these additional settings when iTunes isn’t running.
As with Mac OS X itself, Apple hides a number of iTunes preferences, not making them accessible via a graphical user interface. iTunes Preference Pane installs into System Preferences and provides options for tweaking iTunes. Perhaps the most useful setting is Invert Library Links, which turns the library arrows into links to your own library rather than the iTunes Store (Option-click for the default functionality). The ability to apply half-star ratings will benefit anyone who considers Apple’s default system too restrictive. Note: Make changes to the settings only when iTunes isn’t running.

iTunesMenu stays out of your way.
Plenty of iTunes-notification apps exist, but most take up valuable space on your screen, or get hidden by other windows. iTunesMenu uses your menu bar to display the name of the song currently playing in iTunes, along with other information, such as the artist and album. The drop-down menu also provides access to basic iTunes controls, although we recommend your Mac’s keyboard for those.

Bowtie has a few looks, and you can download more.
Bowtie is similar to iTunesMenu, but instead of displaying the current track’s name in text, it displays the album artwork. Preferences let you define the artwork window’s depth (Desktop level, normal, or always on top). Bowtie includes two alternate themes: one purely text-based, and one with a tiny vinyl record poking out from the artwork. Additional themes can be downloaded (search Google for “bowtie theme”), or if you have knowledge of HTML and CSS, you can make your own.

Lounge resembles the Now Playing screen on Apple TV.
Lounge is an interesting mix of screen saver and iTunes kiosk, and it’s perfect either for parties or just as a good-looking screen saver for any Mac. Instead of iTunes-style visualizer pyrotechnics, Lounge displays the current track’s artwork and information. Options let you toggle keyboard controls for skipping tracks and adjusting volume without exiting the screen saver, flip the screen periodically to avoid screen burn, and even choose a screen saver to switch to when a playlist has ended.

Match all your albums to their artwork in no time.
Album Artwork Assistant beats its artwork-seeking rivals by being comprehensive and offering plenty of choice regarding potential artwork to import. It also provides a queuing system for when you’d like to work through a bunch of albums, rather than immediately applying new art every time. To use this feature, switch Add Immediately for Add To Queue in our walkthrough below (Step 2), and when you’re done, open the Queue drawer and click Process Queue.
Next page: How to Setup iTunesMenu & How to Find Artwork for Your Albums >>
iTunesMenu communicates with iTunes to find out what the currently playing track is. The track artist is displayed in the menu bar, updating as new songs begin. Click the artist name to access the app’s menu. Choose Preferences to configure the display.
Select General and decide what you want displayed in the menu bar. To show the title and artist, separated by a bullet and with a space afterward, type %Title • %Artist into the Status Menu Order field, then click Save Preferences. (Ensure Scrolling is set to None.)
To change the iTunesMenu font, click Select and choose a new one from the Mac OS X Fonts panel. If your Mac keyboard lacks media keys, use iTunesMenu’s Donate section to give $1.99, enter your activation key, and use Hot Keys to define iTunes controls.

Quit iTunes and System Preferences. In Album Artwork Assistant, select Install iTunes AppleScript from the Application menu, then click OK. Select a track or album in iTunes to change its artwork. From the Script menu, select Find With Album Artwork Assistant.

Album Artwork Assistant will display the tracks to be updated. Below this list, the search string used is displayed, along with image results with a resize slider. To choose new artwork for your tracks, select an image and then click Add Immediately.

Album Artwork Assistant may not find artwork right away for obscure releases. Try changing the search string. Alternatively, select the Web Search tab to activate the browser area. Once you find artwork to use, Control- or right-click it and select Add Immediately.
Next page: Scripts Make iTunes Sing >>
AppleScript is something of an unsung hero. It easily automates repetitive tasks, but few users ever go near it. If you’re an iTunes power user, scripts are a must, but you needn’t hack away in AppleScript Editor--many prebuilt iTunes scripts are available online. All you need to do is download them, plonk them in the iTunes Scripts folder, wait a second or two, and the extra functionality is yours.

If you regularly use a script, apply a keyboard shortcut via Keyboard Shortcuts in System Preferences.
The walkthrough below shows you how to set up and manage scripts, so we’ll concentrate on the best available scripts. All of the scripts mentioned are available for free from the Doug’s AppleScripts for iTunes website (dougscripts.com/itunes).
If you’ve got a pretty big music collection, keeping it in good shape can take time--way, way, way too much time. Scripts can assist you with management tasks, taking minutes or seconds to accomplish what might take you hours or more.
One of the best housecleaning scripts is Super Remove Dead Tracks. This finds songs in your library that are no longer available on your Mac. Every 500 tracks, it throws up a dialog to inform you of its progress, and the optional text-based log file at the end tells you which entries have been deleted. On our 13,500-track test library, this entire process took under a minute.
Tracks Without Artwork To Playlist is similar--you select a library, playlist, or an arbitrary bunch of tracks, and the script copies songs without artwork to a new playlist. On activating the script, all you need to do is click Proceed, choose a name for your playlist, and wait for a bit. On our iMac, the script took about 5 minutes to churn through our 13,500 tracks, finding about 1,500 that lacked artwork. With a No Artwork playlist in place, it’s simple to send these tracks to Album Artwork Assistant to grab artwork online.
Another great playlist script is Gather Up The One-Hits. It collects tracks where the artists are each represented in your library by just a single song. Chances are, this will mainly comprise content from compilations, but we found a bunch of one-offs we’d grabbed from the iTunes Store and subsequently forgotten about.
Along with rapidly cleaning up your library, scripts can deal with metadata issues, and you don’t have to open a single Get Info window. Quite often, iTunes downloads inaccurate data when you import tracks from CDs by obscure artists--a common error is the artist and track name fields being reversed. The Swap This With That script from the This Tag, That Tag Scripts compilation can handle this. Launch the script, select a tag to swap from and another to swap to, and your songs’ data is amended. However, be aware that there’s no undo. If your metadata issues are subtler, investigate Track Names To Sentence Caps and Track Names To Word Caps (both of which reformat cases in track names) and Remove N Characters From Front or Back. The last of those enables you to remove a specific number of characters from the start (‘front”) or end (“back”) of a selection of song titles. So if some song titles have track numbers at the start or “disc 1” at the end, this script removes that information quickly and easily.
Scripts can also assist with playback controls. Needle Drop enables you to audition a selection of tracks in automated fashion, after defining playback length and an intro point. For example, you can play 10-second bursts from 2 minutes into every track from a specified playlist.
Another favorite script is Make Bookmarkable, which turns the file type of selected AAC tracks into M4B, thereby making them “bookmarkable,” so playback resumes where you left off. Make UN-Bookmarkable reverses the process.
Search Wikipedia and Google Video Search search the web for more information about your music, working in similar ways: You select a script, and a dialog asks whether you want to search based on the currently playing track or the currently selected track. You then select a category to base the search on. For Wikipedia, you can select the artist, album, or composer. For Google Video, you choose between song, artist, and album. The dialogs aren’t pretty, but they get the job done and save time.

Search for an artist or album on Wikipedia directly from within iTunes simply by using a little script.
Another set of scripts enables you to export track information from iTunes. Although this can be done using File > Library > Export Playlist, the resulting text file is complicated, huge, and unwieldy. Instead, we recommend Album-Artist To HTML Table, which exports a list of your artists and albums (and, optionally, associated tracks, although processing that information takes a long time, so we don’t recommend it) to an HTML document that you can open in a web browser. The script has a couple of quirks: you need to reorder your track list to Album By Artist for best results, and don’t let the script open a browser when it’s finished, or you’ll likely get an error. Instead, click Done and then manually open the HTML file it outputs.
Another export option worth a look is Playlist To Papercdcase.com. It lets you export up to 28 tracks from a playlist to papercdcase.com (the site opens in Safari), which cunningly formats the data into a PDF file that can then be turned into a CD case if your origami skills are up to snuff.

The add-ons mentioned elsewhere in this feature do relatively little to affect the content of your iTunes library. At most, they add a little data here and there, such as ratings and new artwork, and these things are easy enough to revert or delete at a later date. Scripts in iTunes can be a very different matter, because some of them automate complex and “destructive” processes, including reworking and deleting tracks. We’re not trying to scare you off--iTunes scripts can often be very handy timesavers--but we do suggest that you don’t just start using scripts blindly. Before you work with scripts that do anything major to your iTunes library, ensure that you first back it up. The iTunes folder--including your music, other digital content, and databases--lives in the Music directory inside your user folder.

If you haven’t installed scripts before, you won’t have a Scripts folder to use. To add one, quit iTunes, use the Finder to access ~/Library/iTunes (the Library folder that’s found inside your user account’s home folder), and if a Scripts folder isn’t present, create a new folder called Scripts.

Managing scripts is a case of drag and drop. To install a script, drag it into the Scripts folder mentioned in Step 1. To remove one, drag it out of the folder or trash it. It’s best to do such management when iTunes is closed, but iTunes typically tracks script changes well.

Launch iTunes. After installing a script, you’ll see a script icon in the menu bar between the Window and Help menus. This is where you can activate the scripts. Scripts can even have keyboard shortcuts assigned in System Preferences > Keyboard > Keyboard Shortcuts, just like other menu items.