ITunes 9

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Last September, Apple debuted iTunes 8, which brought some major new features (Genius playlists, a new visualizer), a number of refinements for browsing and managing your media (Grid view, better podcast controls), and new iTunes Store offerings (HD TV shows, a new store design). Only a year later, we're already at iTunes 9. (Old man voice: --Why, I remember when Jeff Robbin was still working on Conflict Catcher.) But if you're wondering if the 9 just means "another year gone by," rest assured that the latest iteration of the company's do-everything media program offers a number of significant improvements, including several that have been on wish lists for years.

At the same time, its growing importance in the Apple ecosystem means iTunes is a far cry from the relatively svelte and spry program that debuted back in 2001. The program now handles music, movies, TV shows, music videos, podcasts, audiobooks, iPhone applications, iPod games, ringtones, and Internet radio. It supports purchasing, renting, and importing. It manages iPods, iPhones, and the Apple TV. It coordinates the syncing of contacts, calendars, bookmarks, notes, mail accounts, and even photos. And it manages wireless streaming to remote AirPort and Apple TV units. Whew! The result is an application that offers many features but can be less-than-obvious to use--not to mention a program that can at times get bogged down under the weight of its media burden.

Interface, Take 9

During Apple's music event, the company said that many of the interface changes in iTunes 9--besides the new "shinier" chrome finish, I assume--were designed to make the program easier to use and to make it easier to figure out how to get your media. For example, if you don't have a type of media--say, music--iTunes no longer displays an empty list. Instead, you see a screen that explains how to get music--download it from the iTunes Store or import it from your CDs--along with links to the Store and to tutorial videos. (There's no mention of Amazon MP3, eMusic, or other services, of course.)

Assuming you've already got content in your iTunes Library, you'll see a progress dialog on the initial launch of iTunes 9 as the program updates your iTunes library. (The new version may also update your Genius information; more on that below.) Then you can dig into the new media-browsing features. For example, the Column Browser view now lets you choose between having the browser on top (the pre-9 approach, with the track list below the browser) or on the left (with the track list to the right). The new on-the-left setting gives you a narrower track list that shows fewer columns, but if you have a large iTunes library, it lets you view more items in each column as you browse--a welcome improvement. You can also choose which columns to browse by: any one, two, or three of genres, artists, albums, composers, or groupings.

There are also minor interface changes that will trip up some users. For example, the green "resize" button in the upper left corner of the iTunes window no longer toggles between Mini Player and standard mode; it now zooms the window larger or smaller, just as it does in other programs. (You can still activiate Mini Player mode by Option-clicking on the green button, pressing a keyboard shortcut, or choosing a menu command.) And in Grid view, the header--which lets you change the grid groupings (by artist, album, genre, or composer) and adjust the album-cover size--is disabled by default; you must enable it in the View menu.

Finally, it's worth noting that because it now does so many things, iTunes's interface is becoming more complex. For example, there are now six sections--Library, Store, Devices, Shared, Genius, and Playlist--in the sidebar, each of which contains its own sub-items, and each of those displays its content in the main part of the window. While Apple has indeed made progress in simplifying some aspect's of iTunes's operation, it's no longer the dead-simple program the company once touted it to be.

There's an app for that (and it's called iTunes)

For frequent customers of the iPhone App Store, one of the most frequent requests was for a better way to manage iPhone apps--both in iTunes and on your phone. iTunes 9 makes big, big strides here.

For starters, when you select the Applications item in the iTunes sidebar, you can now view your purchased iPhone apps in list, grid or Cover Flow mode. The icon-free list view is especially welcome for those of us who've downloaded far too many apps, and it lets you view--and sort by--columns for artist (developer), date added or modified, genre, kind, purchase or release date, size, and year. One useful feature that's not available: a way to see which apps are currently installed on your iPhone or iPod touch, and perhaps even rearrange your apps and screens, when the device isn't connected.

But the improvements that generated oohs and aahs from the assembled media at Apple's media event are the new tools for managing what gets synced to your iPhone or iPod touch and how those apps are organized on the device. Select your iPhone or iPod on the left, and then click on the Applications tab to the right: the main area of the iTunes window now shows two columns. The first is a list of all the applications you've downloaded from the App Store; each app's entry in the list shows its icon, name, category (Games, Entertainment, Productivity, and so on), and size. As in iTunes 8, you check the box next to an app to install it on your iPhone, or uncheck the box to remove it, at the next sync.

Even better, you can sort the list by name, category, or date downloaded. (This last option replaces the category display with the date, and it's the date the particular version on your Mac was downloaded, not the date you originally purchased the app.) You can also search the list. These improvements make it dramatically easier to work with the apps you've downloaded, although if you have many apps, the list can be slow to scroll thanks to the app icons.

The second column, though, is perhaps the most-welcome improvement in iTunes 9--at least for iPhone and iPod touch owners. It shows each of your iPhone's actual screens and lets you rearrange apps via drag and drop. To move an app within a screen, simply click on its icon and drag it to a new position; other app icons will move out of the way to make room. To move an app to a different screen, drag the icon to that screen on the right (the list scrolls automatically to show additional screens, although it would be nice if yo ucould resize this area on larger screens to minimize scrolling).

You can even Command-click on multiple icons to move several apps at once, and you can rearrange entire screens by dragging a screen up or down in the list. Heavy users of the App Store, rejoice!

Syncing and media: under new management

It isn't just iPhone apps that get improved management tools. iTunes 9 also improves the options for choosing which media are synced to your iPhones and iPods. For example, the Music tab now lets you choose to sync any combination of playlists (Genius mixes and playlists included), artists, and genres. So, for example, you can easily copy just your favorite three playlists, along with everything by your favorite band, and all tracks classified as Alternative; there's even a search field for the Artists list to make it easier to find particular artists.

Similarly, for movies and TV shows, you can choose to sync recently added (watched or unwatched) items along with specific favorites, as well as movies and shows from selected playlists. And for photos, you can now choose any combination of specific albums, events, and faces (the latter being people identified using iPhoto's Faces feature). Once you've made all your sync choices, the Music tab provides an option to automatically fill any remaining free space with music.

Unfortunately, the Apple TV doesn't get quite as many new syncing options. You do get the new photo-sync options, along with new choices to sync playlists containing movies and TV shows, but the options for syncing music and podcasts remain unchanged.

iTunes 9 also includes two new options for managing your media on your Mac. The first is an option, for users of older versions of iTunes, to reorganize your iTunes media in the Finder. Choose File -> Library -> Organize Library, and then check the Upgrade To iTunes Media Organization option, and iTunes will rearrange your iTunes Music folder into a new iTunes folder with subfolders for Movies, Music, Podcasts, and so on. (This is now the default organization scheme for people starting off with iTunes 9 or creating a new library under iTunes 9.) Although the feature mostly works as claimed, one of my colleagues found that it did leave a few artist-specific folders at the root of the new folder.

The main benefit of this new organization is that it makes it easier to find, using the Finder, particular types of media; the iTunes-8-and-earlier approach had folders for non-music media, but they were buried among separate folders for each music artist. However, if you're considering using this feature, there's one potential caveat: many backup utilities--including OS X's own Time Machine--will consider the moved files to be new files and back them up again, a lengthy and space-consuming process for those with large media libraries.

The other new media-management feature--and it's a feature that's been requested for years--is a folder, created inside your iTunes Music (or iTunes Media) folder, called Automatically Add To iTunes. iTunes 9 periodically checks this folder for new content and adds that content to your iTunes library. If iTunes finds content it can't handle--for example, a good amount of video downloaded from the Internet--it places those files in a Not Added subfolder; inside that folder, each incompatible file is place in its own subfolder named with the date and time iTunes rejected the file. This folder would appear to be the ideal location for saving media files you download from the Internet--say, as the destination for Amazon Downloader, or for podcasts download via an RSS reader--but Apple recommends not placing incomplete files in the folder, which limits the feature's usefulness somewhat.

Finally, if you're a fan of Smart Playlists, iTunes 9 finally brings nested conditionals. Yes, this means you can now create playlist that match any or all of several groups of criteria.

Sharing and share alike

One of the most significant new features--and one that will frustrate some users with its limitations--is Home Sharing. Similar to iTunes 8's sharing feature, Home Sharing lets you listen to music shared by other iTunes users on your local network. But it doesn't stop there.

To set up Home Sharing, you first choose Advanced -> Turn On Home Sharing. Then each copy of iTunes must be authorized (Store -> Authorize Computer) to use a common iTunes account, which means a maximum of five computers can use Home Sharing together. Once multiple computers are authorized, each appears in iTunes's Shared section on the other computers. You can double-click on an audio or video track hosted by another computer to stream it over the network to play it on your own computer.

But there are a few big changes here. First, you can also copy items from a shared iTunes library to your own. For example, to copy a music track from your spouse's library, you just drag it from the track list on the right to your own library on the left (or select the track and click on the Import button); the track is immediately copied and appears in your library. It really, truly is in your library: it will be there even when your spouse's Mac isn't on and running iTunes, and even when you take your MacBook away from home. This isn't smoke and mirrors.

Second, Home Sharing now shares pretty much everything in a library: you can copy music, video, audiobooks, and even iPhone apps--you just drag and drop. Of course, if you copy iTunes-purchased content, in order to use that content you must be authorized for it. For example, if your daughter's library is Home-Sharing linked to yours using your account, you'll be able to freely copy an iPhone app she purchased using her account; in order to use that app, however, your Mac will need to be one of the five authorized to use her content. This can get confusing when you've got multiple people sharing libraries, each of whom purchased content under a different account.

The obvious appeal of Home Sharing is that it finally provides a mechanism for easily copying iTunes content between Macs, but it also provides a couple features that make it easier to keep multiple iTunes libraries in sync. First, if you select a shared library and then choose Items Not In My Library from the Show pop-up menu, the list of contents will be filtered to show only those items not in your own library. (Confusingly, if you select the main library icon for a shared library, only music is displayed; to display apps, movies, or other content, you must first expand the library in iTunes's source list and then select the desired media type.) You can then copy only the items your spouse has added to his or her library that you haven't yet added to your own.

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