iTunes is the ultimate software jukebox (Figure 10-18).
Figure 10-18. iTunes can play music CDs; tune in to Internet radio stations; load up your iPod, iPhone, or iPad; and play music files (including those in the Internet’s favorite format, MP3). It can also turn selected tracks from your music CDs into MP3 files, so that you can store favorite songs on your hard drive to play back anytime—without having to dig up the originals.
The first thing to understand is that iTunes is three apps in one. It’s designed to organize all the music, videos, apps, and ebooks in three places: (1) on your computer, (2) on your i-gadget, and (3) in Apple’s online store.
Apple loves to play with the design of this program; every couple of years, it gets another overhaul. The following pages describe version 12.
In this version, it’s not as clear when you’re looking at the stuff that’s already on your computer—or the stuff that’s on the iTunes Store. The icons at top left (
, 
, and 
, and so on) affect what kind of file you’re viewing; the buttons at top center affect whether you’re looking on your computer or online.
Tip
You can install or remove file-type icons from this top-left “shelf.” For starters, you might want to add the Apps icon (
), so that you can manage your phone’s apps in iTunes. See Figure 10-19.
The playback and volume controls are at the top-left corner of iTunes. At the upper-right corner is a search box that lets you pluck one track out of a haystack.
The following pages take you through the three worlds—computer, store, iPhone—one by one.
Figure 10-19. To edit the “shelf,” click the 
button; from the shortcut menu, choose Edit. Click to place checkmarks next to the file types you want to appear on the shelf, as shown here at right.
The key to understanding iTunes’ layout is the “shelf” of file-type icons at top left. These represent your music, movies, TV shows, apps, and other files that iTunes can manage: (Music), (Movies), (TV Shows), (Apps), 
(Podcasts), 
(iTunes U), 
(Audiobooks), and 
(Tones). (Some are probably hiding in the button.)
To view the music, videos, apps, and ebooks that you’ve downloaded to your Mac, click the corresponding “shelf” icon, and then click one of the “My” buttons at top center (My TV Shows, My Music, and so on).
The button at top right can sort your files or show them as a list. For example, if you clicked , you can see them displayed as Songs, Albums, Artists, Composers, or Genres. And that’s just how they’re displayed; an additional control in this menu governs how they’re sorted.
You may see wildly different things here, depending on which display you’ve chosen. For example, if you click Songs, you see a huge alphabetical list; if you click Albums, you see a square grid of album covers.
iTunes gives you at least three ways to get music and video onto your computer—ready for transferring to your devices, if you want:
Let iTunes find your files. The first time you open iTunes, it offers to search your Mac for music files and add them to its library.
Visit the iTunes Store. Another way to feed your library is to shop at the iTunes Store, as described starting on Editing and deleting playlists.
Import music from a CD. iTunes can also convert tracks from audio CDs into digital music files. Just start up iTunes and then stick a CD into your Mac’s CD drive. The program asks if you want to convert the songs to audio files for iTunes. (If it doesn’t ask, click the CD icon at the top of the window.)
The program downloads song titles and artist information from the CD and begins to add the songs to the iTunes library. (For more control over this process, choose iTunes→Preferences→General (Mac). Use the “When you insert a CD” pop-up menu.)
In that same Preferences box, you can also click Import Settings to choose the format (file type) and bit rate (amount of audio data compressed into that format) for your imported tracks. The factory setting is the AAC format at 128 kilobits per second (kbps).
Most people think these settings make for fine-sounding music files, but you can change your settings to, for example, MP3, another format that lets you cram big music into a small space. Upping the bit rate from 128 to 256 kbps makes for richer-sounding music files—which also take up more room.
Once the importing is finished, each imported song bears a green checkmark, and you have some brand-new files in your iTunes library.
A playlist is a list of songs you’ve decided should go together. For example, if you’re having a party, you can make a playlist from the current Top 40 and dance music in your music library. Some people may question your taste if you, say, alternate tracks from La Bohème with Queen’s A Night at the Opera, but hey—it’s your playlist.
To create a playlist in iTunes, press ⌘-N or choose File→New→Playlist. Type a name for it: “Cardio Workout,” “Shoe-Shopping Tunes,” “Hits of the Highland Lute,” or whatever.
Now click Add To. The screen is now divided into three sections: all your music at left; the selected music in the middle; and your playlist-in-the-making at right. Use any of the buttons in the pop-up menu at top right—Songs, Albums, Artists, whatever—to help you find the songs (or videos); then drag their names into your playlist at far right.
Tip
Instead of making an empty playlist and then dragging songs into it, you can work the other way. You can scroll through a big list of songs, selecting tracks as you go by ⌘-clicking—and then, when you’re finished, choose File→New→Playlist From Selection. All the songs you selected immediately appear on a brand-new playlist.
When you drag a song title onto a playlist, you’re not actually moving or copying the song. In essence, you’re creating an alias or shortcut of the original, which means you can have the same song on several different playlists.
iTunes even starts you out with some playlists of its own devising, like “Top 25 Most Played” and “Purchased” (a convenient place to find all your iTunes Store goodies listed in one place).
Smart playlists constantly rebuild themselves according to criteria you specify. You might tell one to assemble 45 minutes’ worth of songs you’ve rated higher than four stars but rarely listen to, and another to list your most-often-played songs from the ’80s.
Tip
To rate a song, make the window wide enough that you can see the Rating column. (If you don’t see this column, right-click any column heading and choose Rating from the list of options.) Then just click the Rating column for a selected song. The appropriate number of stars appears—one, two, three, four, or five—depending on the position of your click. You can change a song’s rating as many times as you like—a good thing, considering the short shelf life of a pop hit these days.
To make a smart playlist, choose File→New Smart Playlist (Option-⌘-N). The dialog box shown in Figure 10-20 appears. The controls here are designed to set up a search of your music database. Figure 10-20, for example, illustrates how you’d find up to 74 minutes of Beatles tunes released between 1965 and 1968—that you’ve rated three stars or higher and that you’ve listened to no more than twice.
Figure 10-20. A smart playlist is a powerful search command for your iTunes database. You can set up certain criteria, like the hunt for particular Beatles tunes illustrated here. The “Live updating” checkbox makes iTunes keep this playlist updated as your collection changes, as you change your ratings, as your play count changes, and so on.
A playlist is easy to change. Here’s what you can do with just a little light mousework. Start by making sure you’re viewing your library and your music, and click Playlists at the top:
Change the order of songs in the playlist. Drag song titles up or down within the playlist window to reorder them.
Add new songs to the playlist. Click Add To (upper right), and then tiptoe through your iTunes library and drag more songs into a playlist.
Delete songs from the playlist. If your playlist needs pruning, or that banjo tune just doesn’t fit in with the brass-band tracks, you can ditch it quickly: Click the song in the playlist window and then hit Delete or Backspace to get rid of it. When iTunes asks you to confirm your decision, click Remove.
Deleting a song from a playlist doesn’t delete it from your music library—it just removes the title from your playlist.
Delete the whole playlist. To delete an entire playlist, click its name in the list of playlists (far left) and then press Delete. Again, this zaps only the playlist itself, not all the songs you had in it. (Those are still in your computer’s iTunes folder.)
The iTunes software’s second purpose is to be the face of Apple’s online iTunes Store. (Click a file type on the “shelf,” like or , and then click iTunes Store at top center).
Once you land on the store’s main page and set up your iTunes account, you can buy and download songs, audiobooks, ebooks, apps, and videos. This material goes straight into your iTunes library, just a sync away from your i-devices.
Tip
iTunes doesn’t have a monopoly on music sales. Amazon, Google, Rhapsody, and other services sell songs in MP3 format, meaning no copy protection (and Apple compatibility). eMusic.com has great MP3 prices, but the music comes from lesser-known bands. And Amazon’s MP3 Downloader software can whip your purchases right into iTunes.
To navigate the iTunes Store, click the buttons on the file-type “shelf”: (Music), (Movies), (TV Shows), or whatever.
Here it is, the store that made Apple a powerhouse in the music industry: the Music store. Here are millions of songs, individually downloadable, all without copy protection, for 79 cents, $1, or $1.29, depending on popularity.
There are all kinds of ways to slice, dice, and search this catalog. On the right side of the screen, there’s a Genres pop-up menu that sorts the offerings by music type. Use the search box (top right) to find a song by name, album name, band, composer, and so on.
The various buttons on the front page of the Music store represent music Apple thinks you might like: new releases, big hits, Genius recommendations (songs Apple thinks you’ll like based on an analysis of what’s already in your library), and so on.
If you scroll down the right side of the window, you can find lists of the top-selling songs and albums. A handy way to see what the rest of your fellow music lovers are buying, if you don’t mind being a sheep.
Learning these tools for finding songs is handy, because the same tools are available for finding TV shows, movies, podcasts, audiobooks, and so on.
The iTunes store also offers an increasingly vast selection of downloadable TV episodes ($2 apiece, no ads) and movies (some you can buy for $10 to $20, others you rent for $3 to $5).
Once you rent a movie, you have 30 days to start watching—and once you start, you have 24 hours to finish before it turns back into a pumpkin (it deletes itself from your computer or phone).
(If you download a rental movie to your iPhone, you can’t move it to any other gadget. But if you download it to iTunes, you can move it from Mac to iPad, or whatever, although it can exist on only one machine at a time.)
Not everything in the iTunes Store costs money. In addition to free iPhone apps, there are plenty of free audio and video podcasts in the Podcasts area of the store.
Here, for your personal-growth pleasure, are hundreds of thousands of downloadable college courses, all of them free and many of them amazing. Watch the videos of the professors, follow along with the reading materials. You won’t actually earn a college degree this way, but you will attain a degree of enlightenment.
Some people like to curl up with—or listen to—a good book, and iTunes has plenty to offer, both as ebooks (which you buy and read in the iBooks app) and as audiobooks (which you listen to as you work in the garden or commute to work).
If iTunes doesn’t offer the audiobook you’re interested in, you can find a larger collection (over 50,000 of them) at Audible.com. This web store sells all kinds of audiobooks, plus recorded periodicals like The New York Times and radio shows. To purchase Audible’s wares, though, you have to go to the website and create an Audible account.
The files land in iTunes automatically when you buy them.
When Apple says “radio,” it could mean any of several things.
It could mean the free feature called iTunes Radio: custom radio stations, based on songs or singers you like, delivered to you with full pause/skip capabilities and the occasional ad. It’s described starting on iTunes Radio.
It could mean the live, hosted Beats 1 radio station that’s part of Apple’s $10-a-month Apple Music service, described in the box below.
Or it could mean the oldest feature of all: traditional live Internet radio from stations and colleges all over the world. To experience those, click 
on the “shelf,” click the style of music or talk you want, and then double-click a station to start listening.
All movies and TV shows, and some old music files, are still copy protected.
GEM IN THE ROUGH: Apple Music: Unlimited Music for $10 a Month
Apple Music is a $10-a-month service (or $15 for a family of six) that offers you a whole bunch of features.
The big one is a streaming-music service, just like Spotify or Rhapsody. To sign up, open iTunes, click , and then click For You at the top of the iTunes screen.
Once you’ve signed up, you can listen to any band, album, or song in the Apple Music library—30 million songs, on demand, no ads. It’s not like listening to a radio station, where someone else is programming the music; you program the music.
It’s not like Apple’s traditional music store, either, where you pay $1 per download and you own the song forever. If you ever stop paying Apple the $10 a month, the music stops. You’re left with nothing but memories.
Apple Music’s staff also creates ready-made playlists, prepared by human editors, in all kinds of categories. There are sets of starter songs by various singers (“Intro to Sarah McLachlan”), playlists by genre and era, and playlists for specific activities like Waking Up, Running, Getting It On, and even Breaking Up. You can freely mix the songs you’re renting with the music you actually own—in playlists of your own, for example. In fact, you can’t tell which tunes you own and which ones you’re renting.
You can even download songs that you don’t own for playback when you have no Internet connection (as long as you’re still paying your $10 a month).
Apple Music also includes an actual live, hosted radio station, Beats 1 (which is not customized to your tastes). To hear it in iTunes, click , then Radio, and then click the top banner.
There’s also an Instagram-like “channel” of promotional extras from certain bands (click Connect at the top of the iTunes screen).
It’s a lot of features, especially when you try to use it on your phone. But if you love music and you love Apple, the free 90-day trial, at the very least, may be worth a listen.
When you create an account in iTunes, you automatically authorize that computer to play copy-protected songs from the iTunes Store. Authorization is Apple’s way of making sure you don’t go playing those music tracks on more than five computers, which would greatly displease the music studios.
You can copy those songs and videos onto a maximum of four other computers. To authorize each one to play music from your account, choose Store→Authorize Computer. (Don’t worry; you have to do this just once per machine.)
When you’ve maxed out your limit and can’t authorize any more computers, you may need to deauthorize one. On the computer you wish to demote, choose Store→Deauthorize Computer.
The third and final function of iTunes is to load up, and back up, your iPhone, iPad, or iPod Touch. You can connect it to your computer either wirelessly—over Wi-Fi—or with the white USB cable that came with it. (To save precious swaths of forest trees, the rest of this chapter refers to “iPhone” when it means “iPhone, iPad, or iPod Touch.”)
Once the phone is connected, click the 
near the top-left corner of the iTunes screen. Now you can look over the phone’s contents or sync it (read on).
Note
If you have more than one i-device, and they’re all connected, this button is a pop-up menu. Choose the name of the one you want to manipulate.
Pretty simple: Plug one end of the white cable (supplied with your iPhone) to your computer’s USB jack. Connect the other end to the phone. If the phone is turned on and awake, it’s officially connected.
The familiar white USB cable is all well and good—but the iPhone is a wireless device, for Pete’s sake. Why not sync it to your computer wirelessly?
The phone can be charging in its bedside alarm clock dock, happily and automatically syncing with your laptop somewhere else in the house. It transfers all the same stuff to and from your computer—apps, music, books, contacts, calendars, movies, photos, ringtones—but through the air instead of via your USB cable.
Your computer has to be turned on and running iTunes. The phone and the computer have to be on the same Wi-Fi network.
To set up wireless sync, connect the phone using the white USB cable, one last time. Ironic, but true.
Now open iTunes and click at top left. On the Summary tab, scroll down; turn on “Sync with this iPhone over Wi-Fi.” Click Apply. You can now detach the phone.
From now on, whenever the phone is on the Wi-Fi network, it’s automatically connected to your computer, wirelessly. You don’t even have to think about it. (Well, OK—you have to think about leaving the computer turned on with iTunes open, which is something of a buzzkill.)
Just connecting it doesn’t necessarily mean syncing it, though; that’s a more data-intensive, battery-drainy process. Syncing happens in either of two ways:
Automatically. If the iPhone is plugged into power (like a speaker dock, an alarm-clock dock, or a wall outlet), and it’s on the same Wi-Fi network, then it syncs with the Mac all by itself.
Manually. You can also trigger a sync manually—and this time, the iPhone doesn’t have to be plugged into power. To do that, open Settings→General→iTunes Wi-Fi Sync and tap Sync Now. (You can also trigger a Wi-Fi sync from within iTunes—just click the Sync button. It says “Sync” only if, in fact, anything has changed since your last sync.)
Once your iPhone is connected to the computer and you’ve clicked its name at the upper-left corner of iTunes, the left column of the iTunes window reveals word buttons: Summary, Apps, Music, Movies, TV Shows, Podcasts, Books, Photos, Info, and On This iPhone. For the most part, these represent the categories of stuff you can sync to your device. They let you specify exactly what you want copied to it—which songs, which TV shows, which apps, and so on.
Once you’ve made your selections, click the Summary tab and then click Apply. (The Apply button says Sync instead if you haven’t actually changed any settings.)
In OS X, Apple has given you an amazing gift: your own radio station. Your own empire of radio stations, in fact.
GEM IN THE ROUGH: AirPlay Audio
On Arrangement Tab (Multiple Monitors), you can read about the miracle of AirPlay—a wireless technology that sends audio and video from your Mac to your Apple TV.
But even before there was AirPlay video, there was AirPlay audio. Your Mac can easily send audio to your Apple TV (or your AirPort Express base station), and from there to what’s presumably a better sound system than your Mac’s puny built-in speakers.
The official way to do that: Open System Preferences→Sound→Output. Click the name of the Apple TV or AirPort Express in the list of speakers.
But there are two faster ways:
Press Option as you open the 
menulet. The items in this menu magically sprout previously invisible choices—like Apple TV and your other AirPlay gear.
If you just want to play music that’s in iTunes, you can choose your Apple TV’s name (or AirPort Express’s name) from the pop-up menu at the top left of the window.
The iTunes Radio service (Figure 10-21) lets you listen to exactly the kind of music you want to hear. It doesn’t just distinguish among genres like jazz or rock; your choices are far more specific, like “upbeat male vocals with driving brass section” versus “slow lovesick ballads with lots of strings.”
You don’t get to choose the exact songs or singers you want to hear. Instead, you specify a “seed” song, singer, or musical genre, and iTunes Radio does the rest. For example, if you choose Billy Joel as your “seed,” then you’ll hear a lot of Billy Joel, but also a lot of other music that sounds more or less like his.
Figure 10-21. This composite illustration shows the most useful parts of iTunes Radio. Top: You can’t fast-forward or rewind within a Radio song. The progress bar is just a graph that shows you where you are in the song. The numbers on either side show you how far you are into the song and how much is left to play. What you can do, though, is click the > button to open this secret menu. Play More Like This and Never Play This Song let you fine-tune your “radio station,” tailoring it precisely to your tastes. Bottom: Here’s how you create a new station. Click a genre tile or type in a “seed” performer.
Here’s something you can’t do when you listen to real radio: Skip past a song you don’t like. When you tap the 
button, iTunes Radio instantly skips to the next song it would have played. In fact, you can even tell it Play More Like This or Never Play This Song to shape your radio station’s future, as described in Figure 10-21.
Note
You’re allowed to skip up to six songs per hour per station. When you’ve reached your skip limit, the Skip button is dimmed.
In exchange for all this magic, you have to listen to the occasional ad between songs—unless you subscribe to iTunes Match (see the box below), in which case you never hear any ads.
The idea of a “seed song”–based radio service isn’t new, of course. It’s the same idea as Pandora, a website and app that has offered precisely the same features for years. But iTunes Radio is built in, it syncs with the Apple TV, iPhone, and iPad, and it’s so nice to use.
In iTunes, click at the top left; then click Radio on the top bar.
Across the top, you get a horizontally scrolling set of “album covers” (Figure 10-21, top). They represent ready-made “radio stations” that Apple has supplied for you. Click the one called “iTunes Top 100: Pop,” for example, and your Mac instantly begins playing the biggest current pop hits.
Below these, you see bigger “album covers” for radio stations you’ve created yourself, as described next. Scroll down to see them all.
As a station plays, the panel at top center shows the song’s name, band, and album name. And, of course, the price; Apple would be thrilled if you came across a song you liked so much that you wanted to buy it. That’s why the price button ($1.29, for example) is so prominent. When you tap it, the price changes to say Buy Song; tap again to download the song directly. Now you can listen to it again, on demand, without being subject to the randomness of iTunes Radio.
You can set up a new “radio station” of your own in either of two ways: by choosing one of Apple’s canned, ready-to-use stations or by typing in a song or performer you like.
Prefab stations. Tap the
button. Boom: There’s a huge, scrolling list of music genres—Blues, Christian, Classical, Indie Rock, and so on (Figure 10-21, bottom). Tap one to see a list of prefab radio stations, ready to hear.If you tap Jazz, for example, the options include Bop, Early Jazz, Jazz Rock, Latin Jazz, and The Big Band Era. Tap the
to listen a little bit. If you like what you hear, tap Add, just to its right. You’ve just added a new “radio station” to the iTunes Radio main screen.Type in a “seed.” Tap
, and then tap the tiny search box at the top. Type in the name of a singer, band, song, or kind of music (“show tunes” or “a cappella,” for example).In the results, tap the entry that looks most promising (“A Cappella Radio,” for example). You’ve just created a new station, and it begins instantly. Its details page opens, too, so you can fine-tune it.
Tip
If a song comes on that you especially like, the New Station from Artist and New Station from Song options (Figure 10-21) instantly create a new station that will play more music that sounds like this performer or this song. In effect, you get to branch your original station into one that’s more finely tuned to a particular taste.
On the main Radio screen, in the My Stations row, tap the icon of the station you want to mangle or obliterate.
Now you can rename your station (click its existing name) or share it. Using the Play More Like This and Never Play This Song sections, you can add performers, songs, or genres that you want more of or don’t want to be part of this station anymore.
Finally, delete a station by right-clicking (or two-finger clicking) its icon.
To play a song or video in iTunes, double-click it. Or click iTunes’ Play button () or press the space bar. The Mac immediately begins to play the songs whose names have checkmarks in the main list, or from the CD currently in your Mac.
Tip
The central display at the top of the window shows not only the name of the song and album, but also where you are in the song, as represented by the horizontal strip. Drag the handle, or click elsewhere in the strip, to jump around in the song.
As music plays, you can control and manipulate the music and the visuals of your Mac in all kinds of interesting ways. Some people don’t move from their Macs for months at a time.
Visuals are onscreen light shows that pulse, beat, and dance in sync to the music. (For real party fun, invite some people who grew up in the ’60s to your house to watch.)
To summon this psychedelic display, choose View→Show Visuals, or just press ⌘-T. The show begins immediately—although it’s much more fun if you choose View→Enter Full Screen (Control-⌘-F) so the show takes over your whole monitor. True, you won’t get a lot of work done, but when it comes to stress relief, Visuals are a lot cheaper than a hot tub.
You can control iTunes’ music playback using its menus, of course, but the keyboard can be far more efficient. Here are a few of the control keystrokes worth noting:
If you choose Window→Equalizer, you get a handsome control console that lets you adjust the strength of each musical frequency independently (Figure 10-22).
Figure 10-22. Drag the sliders (bass on the left, treble on the right) to accommodate the strengths and weaknesses of your speakers or headphones (and listening tastes). Or save yourself the trouble—use the pop-up menu above the sliders to choose a canned set of slider positions for Classical, Dance, Jazz, Latin, and so on. These settings even transfer to your i-gadgets.