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Building Your Digital Music Library in iTunes

iTunes is all about music (and videos as well), and this chapter is all about getting your music onto your hard drive. Starting with a primer on digital music and video formats, it explains how to rip your CD collection and work with the songs once they are in iTunes.
This chapter is from the book


  • 8.gif About Music and Video Formats
  • 9.gif Import a Music CD into iTunes
  • 10.gif Get CD Track Names Manually
  • 11.gif Add a Music or Video File to Your iTunes Library
  • 12.gif Import Your Existing Digital Music Collection into iTunes
  • 13.gif Add Album Art to Songs
  • 14.gif Submit CD Track Names to the Gracenote Database
  • 15.gif Import a CD with Joined Tracks
  • 16.gif Extract a “Secret Track” into the iTunes Library

iTunes’ foremost function is as a digital music organizer, a way for you to replace your bulky CD collection with a flexible, programmable digital music library that fits inside your computer. To accomplish this, naturally, you’ll have to get your music into iTunes somehow.

Recently, iTunes has added video playback to its repertoire—music videos, TV shows, short films, videos downloaded from the Internet, and even home movies that you make with your own camcorder. Even though the software is still called iTunes, its features include video organizing methods and playback functions that turn it into a complete multimedia jukebox that stores all your favorite pieces of entertainment.

Music you add to the iTunes Library comes from any of the following sources:

  • Imported (ripped) from CDs you already own
  • Imported from your existing collection of MP3, AAC, or unprotected WMA files
  • Imported as an individual music file that you receive or create yourself or one that you convert from an analog format such as a tape or vinyl LP
  • Copied in automatically by iTunes during installation. (See 2.gif Run iTunes for the First Time)
  • Purchased from the iTunes Music Store

Similarly, videos can come from any of the following sources:

  • Created yourself using a camcorder and video editing software
  • Downloaded from the Internet
  • Purchased from the iTunes Music Store

The iTunes Music Store, the method for acquiring new music and videos that requires the least effort and the fewest middlemen, is covered in 18.gif Sign Up for the iTunes Music Store and related tasks in Chapter 4, “Using the iTunes Music Store.” The tasks in this chapter cover the remaining methods of building your music and video collection, particularly the one for which the iTunes interface was primarily designed: importing music from your existing CD collection. The chapter begins with an introduction to the kinds of music and video files you will encounter while using iTunes, and the different types of entertainment items that iTunes organizes for you.

8 About Music and Video Formats

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72.gif Convert Audio Files to Other Formats

No matter how easy to use a piece of software is, there are some trivialities of computer technology that you just can’t escape. One of these bits of esoterica is the plethora of digital music and video file formats that you’ll encounter while using iTunes. Ideally, and for the most common paths of use, file formats are little more than a curiosity you never have to deal with yourself; but the moment you try to do anything at all advanced with your music, you’ll find yourself surrounded by what seems an alphabet soup of acronyms and labels, lurking malevolently just under iTunes’ polished surface. It pays to know what each of these formats is all about and how to deal effectively with it.

Here you’ll learn what the different formats that iTunes recognizes are used for, and—more importantly—how they relate to the different styles of music and video entertainment that iTunes helps you to collect.

Music File Formats

All digital music files follow essentially the same idea: a series of numbers that describe the pitch and intensity of the sound waveform at each particular instant in the audio stream, all adding up to a familiar musical sound when it’s interpreted by software such as iTunes at normal playback speed. Different kinds of files differ, though, in exactly what form those numbers take. Some music formats support compression (the ability to reduce the file size by discarding relatively unimportant sound information, or by indexing small repeated fragments of sound instead of encoding all of them directly—in addition to other, ingeniously mathematical methods). Some formats support Digital Rights Management (DRM), enforcing copy protection. Some forms of digital audio files encode stereo data differently from others, resulting in a somewhat different sound quality. These subtle but important differences are what make some formats more suitable for certain tasks than others, and explain why we have to deal with so many different file formats in the world of digital music.

The following audio file formats are either supported directly by iTunes or destined to be a part of your life as you work with iTunes. Except where noted, the customary filename extension—the three or four letters after the final period (.) in a file’s name—is the same as the acronym of the format listed.

  • CDDA (Compact Disc Digital Audio)— An uncompressed, true stereo digital audio stream made up of a simple series of audio samples. This is the standard format in which every commercial audio CD is encoded and the format in which iTunes burns audio CDs. The CDDA format is essentially interchangeable with AIFF and WAV formats, and it’s almost never used directly on computers.

  • AIFF (Audio Interchange File Format)— An uncompressed audio stream format developed by Apple and popularized as the default sound format of the Macintosh platform. It is still the preferred format for raw audio editing on the Mac. You can convert AIFF files without loss of quality to WAV format and back.

  • WAV (Windows WAVeform file)— An uncompressed audio stream format developed by Microsoft and IBM. Equivalent to AIFF in its supported features and file size, WAV is the default raw audio format for Windows. You can convert WAV files without loss of quality to AIFF format and back.

  • MP3 (MPEG-1 Audio Layer 3)— Developed in the early 1990s as part of the MPEG video/audio compression specification, MP3 is the first audio format to have brought the file size of individual song tracks down to the point where they could be easily transferred across the Internet while still sounding nearly true to the original CD-quality sound from which they were derived. Encoding technology for MP3 files is subject to patents held by Thomson Consumer Electronics and the Fraunhofer Institute, which contributed to the format’s original design. MP3 is a lossy compression format, meaning that any music converted to MP3 format cannot be flawlessly converted back to its original format; some music data is inevitably lost. The benefit is that an MP3 file usually achieves about a 12:1 compression ratio over the uncompressed source, depending on the bit rate you select during encoding.

MP3’s compression is achieved through a number of techniques, including the discarding of superfluous (inaudible) audio data and the application of psychoacoustics. Stereo information is usually done in “joint stereo” mode. That means that instead of two separate tracks for the left and right channels, most information is recorded as a “mono” track and a separate channel records the separation from left to right, which saves on file size. Also, Variable Bit Rate (VBR) encoding is frequently employed to encode lower-complexity sections of music at a lower bit rate, saving space without sacrificing audio quality.

MP3 files have no DRM technology built in, so there is no way for a copyright holder to control or track the spread of an MP3 version of a song. MP3 files do, however, have info tags—also known as ID3 tags—that allow the user to embed a wide variety of organizational information into the file’s text headers. This information does not interfere with the audio stream, but it gives software such as iTunes the ability to organize MP3 files with much better control and flexibility than with filenames alone.

In iTunes, an MP3 file is identified in the Kind column as MPEG audio file.

  • AAC (Advanced Audio Coding)— The official successor to MP3, AAC (another lossy compression format) is the latest iteration of the audio specification in the MPEG standard, part of the MPEG-4 framework that underlies modern versions of QuickTime. Apple is currently the most visible company using AAC in its products, although it is far from being a “proprietary” format; the only thing proprietary about AAC as used in the iTunes Music Store is the way the DRM scheme (known as FairPlay) is keyed to individual purchasers. Functionally, however, as far as any company that wants to interoperate with music purchased through iTunes, Apple’s format is essentially closed.

    03fig01.jpg AAC files incorporate many advances over the earlier MP3 format, including as many as 48 distinct audio channels, a more dynamic form of stereo encoding, and a notably smaller file size for files that are encoded with the same subjective sound quality. This means that if you encode your CD collection in AAC format instead of MP3, you can save about 25 percent of your disk space (which, remember, also applies to the space available on your iPod). AAC supports all the same info tags that MP3 does.

    There are two flavors of AAC as used in iTunes: protected and unprotected. Protected AAC files are keyed to an individual purchaser’s identity and cannot be opened on a given computer unless that computer has been authorized with the central iTunes authorization servers; as many as five separate computers can be authorized at one time for a single purchaser account. (See 23.gif Authorize a Computer to Play Purchased Music for more information.) Unprotected AAC files are as freely portable and playable as MP3 files are; you can send an unprotected AAC file to anyone else with iTunes or any other software capable of reading AAC files, and the recipient can play it successfully. When you import music from your CD collection, iTunes creates the digital music files by default in unprotected AAC format.

    AAC files are identified by either an .m4a (MPEG-4 Audio) or .m4p (MPEG-4 Protected) filename extension, depending on whether the files are protected with DRM.

  • WMA (Windows Media Audio)— Microsoft’s answer to MP3 (and later, to AAC as used in iTunes), WMA is a lossy compression format that is entirely proprietary and owned by Microsoft. Its capabilities are comparable to those of AAC—the audio quality for a given file size is considerably better than with MP3, and thus for the same audio quality you get significant file size savings. WMA also comes in both protected and unprotected flavors. iTunes for Windows can import unprotected WMA files by converting them to AAC on-the-fly.

    The DRM scheme in WMA files as sold through the online music stores that compete with the iTunes Music Store is flexible and is implemented differently by various sellers. Some stores restrict copying and playback to a certain number of computers, like iTunes does. Others, like Napster’s subscription service, enforce an expiration date beyond which you cannot open a file; periodic authorization is required to extend the expiration date on these files. Still other services set a limit on the number of times you can play a given song before it becomes locked.
  • Apple Lossless— A format developed by Apple and released with iTunes 4.5 in April 2004, with the intention of supporting high-quality audio storage for professional musicians and audiophiles without requiring the full amount of disk space required by uncompressed AIFF, WAV, or CDDA data. Apple Lossless achieves compression of about 2:1 over the uncompressed source data by using techniques similar to those found in GIF or ZIP files (both compression formats that must by their nature be totally lossless). If you encode your music using Apple Lossless, expect to consume about 5 megabytes (MB) of disk space for every minute of music; but this music will be at true CD quality without even the minimal degradation of quality found in MP3 or AAC formats. Apple Lossless files are encapsulated in MPEG-4 wrappers; thus, they have an .m4a filename extension. These files are not, however, AAC files.

  • MIDI (Musical Instrument Digital Interface)— Completely unlike all the preceding formats, MIDI is not a series of samples at all, but a synthesized music format. MIDI files are generally tiny compared to sampled music files such as AAC and MP3—only 20 to 50 kilobytes (KB)—because all they contain are lists of commands comparable to what you would see on a piece of sheet music. MIDI files depend on a library of playback technology to interpret these commands, as an orchestra would read the sheet music in front of it; both Windows and Mac OS X can play MIDI files natively, but the playback quality of a MIDI file depends greatly on the quality of the synthesized instruments in the software you use. iTunes can add MIDI files to its Library and play them using the QuickTime MIDI instruments, but you cannot transfer these files to the iPod. MIDI files generally have a .mid extension.

iTunes lets you convert between most of these formats, if not bidirectionally, at least from each to a native format such as AAC or MP3. In the tasks in this chapter, you will see how to take advantage of the strengths of these different formats as you bring in your music from varying sources to consolidate it into your digital iTunes Library.

Video File Formats

Video files have their own set of formats, each defined by the company or software that originally popularized it. Some video formats are just frameworks that can support many different codecs (encoding and decoding algorithms); others are more monolithic in nature, with the format and the codec being synonymous. What you have to know is that iTunes works with all the video formats supported by Apple’s QuickTime multimedia architecture, but the iPod supports a much more limited range of file formats.

  • MPEG— Developed by the Moving Picture Experts Group in the early 1990s, MPEG (whose files end in .mpg or .mpeg) is a format that’s widely supported on all computing platforms, including QuickTime and iTunes. The original MPEG standard (MPEG-1) contains the specification for MP3 audio files, as described earlier. The audio and video tracks in an MPEG file are multiplexed or “muxed,” meaning that they’re tied together and cannot be independently edited. In iTunes, an MPEG file is listed in the Kind column as QuickTime movie file. Because MPEG’s compression technology is not particularly advanced (and thus its quality-for-file-size compromise is not ideal), MPEG files are not supported on the iPod; however, iTunes can convert them to an iPod-compatible format. (See 47.gif Put Your Home Movies and Downloaded Videos on Your iPod.)

  • AVI— The Microsoft multimedia container format, Audio/Video Interleave is a framework developed in 1992 that supports a wide variety of different codecs. The most popular video format on the Internet today (used for distributing illicit recordings of movies and TV shows, in the same way that MP3 files became the preferred format for digital music piracy) is AVI with the DiVX codec or one of its relatives. Even though QuickTime can play AVI files as long as it recognizes the codec, you cannot import AVI files into iTunes or transfer them to the iPod.

  • Flash— Popularized in the late 1990s by Macromedia (now Adobe), Flash is very different from the other types of video files listed here. It’s a sprite animation framework that uses vector images described by mathematical curves. This approach results in quite small file sizes even for long-running videos; thus, Flash has become very popular for distributing movies over the Internet. However, Flash files (with an .swf) extension) are supported only to a limited extent by QuickTime and cannot be added to iTunes or transferred to the iPod.

  • Windows Media— A comparatively recent development by Microsoft, Windows Media Video (.wmv) files are a proprietary standard being popularized by the movie-making tools that are built into Windows, and they are one of the more common video formats on the Internet today. (WMV is the video counterpart to WMA.) Windows users can play WMV files natively in Windows Media Player; Mac users can play them in the QuickTime player using a free plug-in from Flip4Mac and Microsoft (http://flip4mac.com/); this plug-in also allows Mac users to import WMV files into iTunes. However, you cannot transfer these WMV files to the iPod, and because a plug-in to add WMV support to QuickTime is not available for Windows, you can’t add WMV files to iTunes in Windows.

  • QuickTime— Apple’s own venerable video framework, QuickTime files work like AVI files in that they can use any of a myriad of different codecs, including very modern ones such as MPEG-4. The .mov extension can be confusing; it indicates a QuickTime wrapper on a movie file that can be self-contained or just consist of a pointer to another file or set of files on your disk or on the Internet. Most .mov files that you find on the Internet are in a popular codec such as Sorenson 3 or MPEG-4/AVC (H.264) and can be used in iTunes with no trouble. However, you have to convert some QuickTime files to a compatible format (see 47.gif Put Your Home Movies and Downloaded Videos on Your iPod) before you can transfer them to the iPod.

  • MPEG-4— The newest iteration of the MPEG standard is the native and preferred format for both iTunes and the iPod. It’s also the foundation for the modern QuickTime architecture. MPEG-4 files can contain any of several different codecs, but the most efficient one (and the one used by iTunes and the iTunes Music Store) is H.264, also known as AVC (Advanced Video Coding), which enables videos to display a broadcast-quality picture at a file size that is suitable for downloading. As with AAC audio files, MPEG-4 files come in both protected and unprotected varieties, although both use the extension .m4v (MPEG-4 Video). Unprotected MPEG-4 files also use that extension. You can import any MPEG-4 video file into iTunes and transfer it to the iPod for portable viewing.

In summary, iTunes can import and play MPEG, AVI, QuickTime, and MPEG-4 files (and WMV files if you have a Mac and the Flip4Mac plug-in). To transfer movie files to the iPod, you must ensure that they are in MPEG-4 format, although iTunes can convert several kinds of files to MPEG-4 for use on the iPod.

Styles of Music and Video in iTunes

iTunes distinguishes between a number of different kinds of entertainment media, depending on how the media is presented and what mechanisms exist for organizing it. Following is a list of the different kinds of media you’ll find in iTunes:

  • Digital music— Any music, spoken word, comedy, or other audio that you would normally expect to find on CDs. This is the bulk of what you’ll collect in iTunes, and iTunes’ primary goal is to make the navigation and playback of your digital music as versatile as possible. Digital music can be in MP3, AAC, AIFF, WAV, Apple Lossless, or MIDI formats (although MP3 and AAC are the most common). Digital music is organized in the Library, which is at the top of the iTunes Source pane.

  • Podcasts— A podcast can be anything from a simple downloadable MP3 file of a guy talking, to a multichapter audio stream of music, comedy, politics, and commentary with artwork displayed at each named chapter marker, or even a video stream in MPEG-4 format. Because a podcast is episodic in nature, with new episodes being released on a regular basis (often weekly), you subscribe to a podcast using the URL (Web address) of its RSS feed (see 30.gif Watch for Newly Added Music Using an RSS Feed) or by selecting it in the Podcast directory of the iTunes Music Store. iTunes then downloads new episodes when they become available, and it alerts you to episodes you haven’t played yet using a blue dot that also appears next to the episode’s listing on the iPod. Podcasts by default support automatic bookmarking, which means that iTunes keeps track of your place when you stop listening to the audio stream and resumes at that point when you play the podcast episode again. It even synchronizes the bookmark to the iPod so that you can go from iTunes to the iPod and have the episode always pick up right where you last left off. See 39.gif Subscribe to and Listen to Podcasts for more details.

  • Audiobooks— An audiobook is the digital equivalent of a book on tape. Spoken narration of a book is recorded into a long audio file, usually in AAC format, and distributed in several parts that can each last for hours. A single audio file representing a part of the book can have its own subdivisions, or “chapters,” that you can skip to using the selector that appears next to the status display in iTunes when you’re playing it. Audiobooks support automatic bookmarking, making sure that you don’t lose your place in a long stream of narration. The iPod, additionally, can speed up or slow down the playback speed at which the audiobook is read without affecting the pitch of the narrator’s voice. Audiobooks are organized with your digital music in the iTunes Library, and they have their own listing in the Music menu on the iPod; see 56.gif Listen to an Audiobook or Podcast at Home or on the Go for more information.

  • Internet Radio— A “stream” of audio data (usually in MP3 format) coming from a source on the Internet, Internet Radio data cannot be saved directly by iTunes, paused, rewound, or scanned using the scrub bar—it’s a live stream to which you connect by specifying a web address to listen to. Favorite Internet Radio streams are added to your iTunes Library as you listen to them so that you can return to them whenever you want, but (naturally) you cannot transfer them to your iPod. Internet Radio streams sometimes use downloaded “playlist” files to schedule the playback of tracks that are stored on the server. Refer to 40.gif Listen to an Internet Radio Station for more information.

  • Movies— This category of video files indicates standalone items such as short films from Pixar and Disney, home movies, and videos you download off the Internet, which can be in QuickTime or MPEG-4 format in iTunes, and only in MPEG-4 format on the iPod. Movies that you buy from the iTunes Music Store have automatic bookmarking turned on by default, allowing you to keep your place and return to the movie later. Other movies have to have bookmarking turned on manually to keep track of their playback positions.

  • Music videos— A specific category of videos that you can buy from the iTunes Music Store, music videos are just like the ones you would see on MTV—popular songs set to video. These files do not support automatic bookmarking by default (they’re usually no longer than a typical song, so bookmarking isn’t really important), but you can turn it on for individual files if you want.

  • TV shows— Released sequentially as they’re broadcast new, and in complete “seasons” (analogous to “albums” for music), TV shows are episodes of popular television series from any of more than a dozen popular networks. Because they have no commercials, half-hour episodes last for about 22 minutes and hour-long episodes are 45 minutes, although some cable shows that were designed to be broadcast without commercial interruption last for the complete hour. TV shows support automatic bookmarking so you won’t lose your place in iTunes or on the iPod.

  • Booklets— Presented as premiums in the iTunes Music Store, usually accompanying special packaged sets of digital music such as the $150 The Complete U2, digital booklets are computerized versions of the books you might expect to get in a premium CD or boxed music set at the record store. Containing such things as lyrics, biographies, interviews, cover art, and artist commentaries on the music it accompanies, booklets are listed in the iTunes Library along with the artists and albums to which they pertain.

These subdivisions of your audio and video files allow you to narrow your searching scope when you search for music or videos using the Search box. (See 33.gif Find and Play Music in iTunes for more information about searching.) Be sure to familiarize yourself with the subtle differences between each of these types of media, because when you want to dial up a specific podcast episode, audiobook chapter, or TV show episode on your iPod, you need to know what groupings to look for on the way to your desired content.

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