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Although Apple has sold more than 1.5 billion songs through the iTunes Store, most of the tunes that most people listen to come from the CD collections they’ve amassed over the years. But ripping those CDs into iTunes can be a time-consuming process—especially if you decide to reimport your music later (because you want a different bit rate or because a better format has come along).

For instance, you may want to put AAC files on your iPod, you may want MP3 duplicates of your songs to use with music-streaming hardware such as Slim Devices’ Squeezebox, and you may want the highest-quality files possible when you use AirTunes to listen to music on your home stereo. It may be time to consider Apple Lossless encoding—and never have to rip a CD more than once.

Why lossless?

If you’ve ever expanded a compressed file set—a Zip file or a StuffIt archive, for example—you know that what you get after expansion is exactly the same as what was put into the archive: complete photos with no quality loss, documents with exactly the same text or data, and so on. This idea of lossless compression can also be applied to music. In iTunes 4.5, Apple added the Apple Lossless Encoder (ALE) to its encoding repertoire. Lossless encoding creates files that are from 30 to 70 percent of the size of uncompressed AIFF or WAV files, but it does so without compromising sound quality (something that lossy encoding schemes such as AAC and MP3 can’t do).

Ripping your CDs as lossless files is useful in a few ways. The sound quality of lossless files is equal to that of your original CDs—so they’re good for listening to on a home stereo and for creating mixed CDs. Lossless files take up less space than uncompressed files. And they give you the option of creating other compressed versions of your songs.

Although compressed, lossless files are still much larger than typical AAC and MP3 files. Their size can be a problem with iPods, on which space is limited (but keep in mind that iPods’ capacities continue to increase). However, size is much less of a concern on your Mac. The days of expensive storage are long gone; you can buy a huge internal hard drive for relatively little money—up to 750GB for around $350—and external drives cost only a bit more. ALE compression rates vary based on the complexity of the music, but with an average of 300MB per album, you could put the equivalent of 1,000 CDs on a 300GB hard drive—plenty of room for most collections.

Ripping lossless files

You probably know that you can set iTunes’ encoder to rip to different formats. To rip lossless files, go to the Importing tab of iTunes’ Advanced preference pane, select Apple Lossless Encoder from the Import User pop-up menu, and rip your CDs as normal (see “Rip for Life”). Unlike with AAC or MP3 files, you don’t choose a bit rate for lossless files. If you’ve already ripped a CD in a different format, iTunes will ask whether you want to replace the existing files. Click on Don’t Replace to tell iTunes to store both copies of the files. Typically, iTunes imports lossless files faster than compressed files, since your Mac’s processor doesn’t have to do as much work to compress the music. The lossless files will be larger than lossy files, but everything else about lossless files is the same. You can change tag information, add album art, and include lyrics, for example.

Once you’ve imported lossless files, it’s easy to use them to create files in other formats. Go back to iTunes’ Importing tab and change the format and bit rate to your liking. Then pick the lossless files you want to convert (if you’re converting many files, add them to a playlist first and then select them), and choose Convert Selection To Format Name from iTunes’ Advanced menu—iTunes will create new files in your selected format while keeping the original lossless files in your library. Converting a lot of files can take a long time, so you might want to encode overnight if you’re converting hundreds of songs.

You can convert the lossless files into as many formats as you need: 128 Kbps AAC files for an iPod nano, higher bit-rate AAC files for an 80GB iPod, or MP3 files for a streaming device or non-Apple music player. (If you want to burn a CD from lossless files, just create a playlist of the songs you want and start burning—you don’t need to convert them to AIFF, since iTunes does this on-the-fly as it burns the disc.)

Working with multiple file formats

If you decide to go the lossless route, you’ll need a strategy for managing the same music in multiple formats in your iTunes library. There are two ways to do this: you can store all your files in the same library and then use playlists to separate them by format (helpful for copying the right versions to your iPod), or you can create a second library.

If you often play lossless files (on your home stereo, say) the two-library solution is your best bet—when you want to listen to music, you can just switch to your lossless library. With iTunes 7, you can now create multiple libraries without the need for a third-party app. To access the feature, you hold down the option key when you launch iTunes to create or choose a library. Although I’m glad Apple added support for multiple libraries, I prefer using a different application—such as Doug Adams’s iTunes Library Manager 5.0.1 ($10) or Steve Roy’s Libra 2.1 (payment requested)—that stores not only the locations of your songs and playlists, but also your individual iTunes preferences with each library. iTunes 7 doesn’t keep separate preference information.

However, all of these files can take up a lot of space. To store the second library’s lossless files on an external hard drive, first create a folder for your music on that drive; then go to the General tab of iTunes’ Advanced preference pane, click on the Change button next to the iTunes Music Folder Location file-path box, and navigate to the folder you created. After ripping your CDs, you can use one of the aforementioned library managers to switch between this archival library and your primary library.

Getting files into the right library does take a bit of work. You can convert files only when the lossless library is active; then you have to copy the converted files to a central location (drag them from your lossless library to the desktop or to a folder in the Finder)—or try to find them in the iTunes Music folder. When the files are copied, delete the con-verted files from the lossless library, switch to the library you want the files in, and drag them to iTunes’ main window to add them to that library.

Using playlists makes managing your music easier, but you need enough disk space to store both your lossless files and your AAC or MP3 files. If space is no object, playlists are a good choice—you won’t have to worry about switching libraries and copying files. To keep the files separate, you can create smart playlists with conditions such as Kind Contains AAC or Kind Does Not Contain Lossless, and then sync the desired playlists with your iPod.

Another option is to deselect the lossless files and then choose Only Update Checked Songs in the General tab of iTunes’ iPod preference pane. (To deselect all your lossless files at once, create a smart playlist with the condition Kind Contains Lossless, hold down the Command key, and click on the check box to the left of the name of any file in the playlist.)

Beyond iTunes conversion

iTunes lets you convert Apple Lossless files to many other formats. But what if you want a format that iTunes can’t handle, such as FLAC (Free Lossless Audio Codec)—a lossless audio format supported by audiophile hardware such as Slim Devices’ Squeezebox and Sonos’s Digital Music System? Then check out Stephen Booth’s Max 0.6.1 (free), an app that converts files to and from Apple Lossless—and more than a dozen other formats. Max works with the formats that iTunes supports, Ogg Vorbis, popular lossless formats such as FLAC and Monkey’s Audio (APE), and many others. Max is fast and easy to use, and it lets you tweak your conversion settings as much as you want. More and more audiophile devices offer FLAC support but don’t support Apple Lossless. Max can convert your files to work with whatever streaming-audio device you have.

[ Kirk McElhearn is the author of several books on the Mac and the iPod, including iPod and iTunes Garage (Prentice Hall, 2004). His blog features articles about OS X, the iPod, and iTunes. ]

Rip for Life: Select Apple Lossless Encoder to rip CDs as lossless files that you can later convert to almost any format.Make a Change: With iTunes Library Manager, you can create many different iTunes libraries and then easily switch between them.
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