ITunes 9

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.

Even better, iTunes can automatically check for new items in another library and copy them to your own. Configuring this feature is as simple as clicking on the Settings button while viewing a Home-Shared library, choosing the types of media you want copied, and clicking on OK.

This sounds like a great feature, and in some ways it is. But as my colleague Peter Cohen explained yesterday, it also has some sizable limitations. The biggest--and it's a doozy--is that the automatic-transfer feature works only with content downloaded from the iTunes Store. (The text of the Settings dialog, Automatically transfer new purchases from..., implies this, but we confirmed the limitation both with Apple and through our own testing.) So while you can manually copy media ripped from your own CDs and DVDs, music purchased from Amazon MP3 and eMusic, and other content you didn't get from the iTunes Store, that content won't be copied automatically. This auto-transfer limitation would appear to be a nod to music industry concerns about piracy, but for many people, it cripples the ultimate usefulness of a very cool feature. (See Peter's article for a number of other issues.)

It's also worth nothing that Home Sharing isn't a way to maintain a central iTunes library that syncs with multiple Macs or user accounts in the same household. Besides the auto-transfer feature being limited to iTunes-purchased media, tracks copied via Home Sharing don't maintain metadata such as ratings or playcounts, nor can you transfer or sync playlists. iTunes 10, anyone?

Still, despite the auto-transfer limitation, this is a handy new feature that makes it much easier to ensure all your Macs have all your media.

More Genius in more places

iTunes 8 debuted Genius playlists, which can create a playlist based on a "seed" track. To work this magic, iTunes anonymously uploads information about all the music in your library and compares that info to other people with similar music libraries. When you create a Genius playlist, that data is used to choose a list of 25 to 100 songs in your library that other people with similar music tastes also have. In other words, iTunes creates a playlist it thinks you'll like if you like the seed track.

iTunes 9 uses that same data--data on over 54 billion songs, according to Apple--to create Genius Mixes. Instead of requiring you to pick a seed song to create a playlist, the Genius mix feature goes through your library and chooses tracks that "go great together."

Unlike Genius playlists, your Genius mixes are created automatically and contain as many tracks as you have that fit the mix. When you select the Genius Mixes item in the iTunes sidebar, the main area of the iTunes window displays your mixes. Each mix is displayed as a composite album cover; mouse over a cover to view, at the bottom of the window, the name of the mix and a sampling of artists it contains ("Based on Coldplay, Travis, Keane, & others," for example). With my library of 14,000 or so music tracks, iTunes created the maximum 12 Genius mixes--with smaller libraries, you end up with fewer--with names such as Rock Mix, Electronic Mix, Alternative Mix, and Alternative Mix 2. Click on a mix to being playback.

In my brief testing, the feature was generally good at grouping similar types of tracks, and made for enjoyable playlists, although the mixes were clearly biased in favor of the types of music--rock, pop, hip-hop, classic rock, and new wave--that dominate my music collection. My library contains quite a bit of jazz, classical, and folk, yet because these genres are in the minority, iTunes didn't create a single mix for them.

On the other hand, Genius mixes are like a black box: there's no way to view the tracks in a mix, to edit the mix, or even to delete a mix you don't like.

I also experienced one other glitch that was initially a show-stopper. In order to use the Genius Mixes feature, iTunes needs to update your library's Genius information. This should happen the first time you launch iTunes 9. (If you canceled this process the first time you ran iTunes 9, just choose Store -> Update Genius.) But for me, this process never ended--the progress bar at the top of the iTunes window never finished, and the Genius Mixes item never appeared in the sidebar. I've seen a good number of reports from other users around the Web experiencing the same issue.

As today's Bugs and Fixes column explains, the problem appears to be caused by particular apple.com entries in your Mac's cookies.plist file. To fix the problem, I had to quit iTunes, open the Security screen of Safari preferences, click on Show Cookies, and delete all iTunes-related apple.com cookies. After relaunching iTunes, my Genius information was updated relatively quickly and the Genius Mixes item appeared soon after.

There's also one more place where iTunes 9's Genius feature appears: Once you've upgraded your iPhone or iPod touch to iPhone OS 3.1, the App Store app displays a new Genius screen that recommends new apps based on apps already installed on your device.

The iTunes Store gets a facelift...again

Finally, as with each recent upgrade to iTunes, Apple has redesigned the iTunes Store and added some new features and purchasing options. The new design is a bit less cluttered and offers more options for jumping directly to particular content. For example, mouse over the Music item in the navigation bar and a small arrow appears; click on the arrow to view a menu for jumping directly to a particular music section--videos, iTunes Essentials, pre-orders or any music genre. Each section page provides side-scrolling groups of album thumbnails that I found a bit easier to browse than the previous design.

Album pages also get a new look that does away with a separate track-list pane at the bottom, instead placing the track list in the body of the page. This new appearance is more attractive and wastes less space, but it isn't without drawbacks: You don't see the track-preview button until you mouse over a track name, and you can no longer use the arrow keys or back/forward buttons to skip through previews of an album's tracks. (And you still can't click on a single button to preview all tracks on an album, something you've been able to on many other music services for years.)

For those with smaller screens, there's a useful new setting, in iTunes preferences, to hide the source list and use the entire window when browsing the store, and those with large screens will appreciate that the store grows to efficiently fit the iTunes window no matter how large it gets. People who use Twitter and Facebook can post a message about a particular item by clicking on the arrow next to the item's Buy button and choosing Share On Twitter or Facebook, respectively. And one of my favorite new features is that a track preview no longer stops playing if you navigate away from the page containing the track.

Although the new design may make it easier to find media, in the two days since iTunes 9 debuted, navigating the store was at times an exercise in frustration. Sometimes pages didn't load at all, and when they did, the transition often took a minute or more. For now I'll chalk this up to heavy traffic, but I don't recall the same issues when iTunes 8 debuted.

Apple has also done away with the shopping cart; the only way to buy content in iTunes 9 is One-Click purchasing. If you were one of the many people who used the shopping cart as a sort of "wish list," not to worry--iTunes 9 now includes a dedicated wish list feature. Click on the arrow next to a Buy button and choose Add To Wish List, and that item is added to your list for later consideration or purchasing. You can access your wish list from the Quick Links section on the iTunes Store home page (where it conveniently notes how many items are on the list), or at the bottom of any other page in the store. One limitation, however, is that not all items can be added to your wish list; for example, I noticed I couldn't add some iTunes Passes.

Finally, there are two new types of content you can purchase from the iTunes Store: iTunes LPs and iTunes Extras. iTunes LPs are the music industry's latest attempt to get people to purchase albums instead of individual tracks. Each iTunes LP includes the album's full track list, along with full-screen extras--designed with input from the actual artists--such as music videos, video interviews, liner notes, discographies, and lyrics. They're a fun option for hardcore fans, even though in many ways they remind me of the music-focused CD-ROMs of the '90s (though with better quality multimedia).

Unfortunately, there aren't many iTunes LPs available right now--just 11 albums (five of those pre-orders) and one "comic book and single"--and you pay a premium for them: The iTunes LP version of Dave Matthews Band's latest, Big Whiskey and the GrooGrux King, is $20, and The Grateful Dead's American Beauty is $14 (compared to $10 for the standard version). And the tracks themselves are the same 256kbps AAC files you get with the standard versions; for many music lovers, it would be easier to justify the premium if iTunes LP also included higher-quality files.

iTunes Extras are similar to the special features--deleted scenes, interviews, and the like--you get with many DVDs, and are now included with select (currently 14) movies from the iTunes Store. The absence of these features has kept many movie buffs from purchasing movies from the iTunes Store. I purchased Wall-E and enjoyed these extras, which play in the iTunes window and include "live" tours of set pieces and places, storybooks, making-of clips, videos inspired by the movie, robot schematics, set fly-throughs, deleted scenes, and a useful chapter menu. Unlike iTunes LPs, there's no big price premium here: movies with iTunes Extras appear to be the same price as the movie alone sold for previously. For example, Wall-E is $15, and The Bourne Ultimatim is $10. Note that these Extras won't play on your iPod, iPhone, or Apple TV.

There doesn't appear to be a way to upgrade to the iTunes LP version of an album or the iTunes Extras version of a movie if you've purchased the standard versions of those albums or movies in the past.

Macworld's buying advice

iTunes 9 isn't without drawbacks. In addition to the Genius-update issue I and some other users have experienced, performance is occasionally an issue. Besides the specific examples I already noted, I found iTunes 9 would at times stall when checking Home Sharing libraries for new content, and I experienced several iTunes crashes over the past few days of use.

Still, even given those concerns, I suspect most users will want to install iTunes 9 soon--especially since it's a free download. Besides being a mandatory upgrade if you need to use any of the new features of the iTunes Store and your iPhone or iPod touch, the latest version of iTunes is a worthy upgrade for new users, those with massive media libraries, and those who want to more-easily share their media between family members. Indeed, Apple's goal with iTunes 9 seems to have been to make it easier for new users to bring in media and start enjoying it, while providing some of the most-requested features for existing users. And in most respects, iTunes 9 succeeds.

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