iTunes is a truly historic piece of software. It’s gone from a simple jukebox to the most popular media management software in the world, picking up a long list of features along the way. Keeping this legacy going is the latest version, iTunes 11, a major redesign that aims to dispell the opinion that iTunes is bloated and outdated. Read on to hear my thoughts on whether it succeeds.

Interface

iTunes 11 is the biggest visual refresh in the software’s history. It has a new toolbar gradient, a darker, sleeker playback panel, and an all-around cleaner look. The sidebar and status bar are hidden by default, in favor of a simple toolbar along the top. You can show them again by using the View menu. The sidebar’s been consolidated into a popover menu in the toolbar, and connected iOS devices get their own button next to the iTunes Store button on the right.

View modes are gone in iTunes 11. Instead, albums are displayed in what Apple is calling “Expanded View”. This works like a folder on iOS: You click on an album’s artwork, and the interface splits and expands into a subview with a song list and an “in the store” section, which shows top songs and albums for that artist. Expanded View is intelligent enough to pull out the dominant colors in your album’s artwork, which are used to color the background and text, with a copy of the album’s artwork on the side. Expanded View is fun, and works better than the iTunes 10 model, which required you to back out of an album’s song list to see your album list. When viewing your artists, you get a list of artists on the left and the selected artist’s albums on the right. The traditional list view is still there when viewing songs, and you can even show the old-school column browser if you’re so inclined.

iTunes uses Helvetica now instead of OS X’s system font, Lucida Grande. iOS’s system font is also Helvetica, and with Apple’s trend of bringing iOS qualities to OS X it could be that the next major version uses Helvetica as the system font instead of Lucida Grande.

While the new iTunes interface is pretty, it still has a lot of ugly dialogs from the past, like the one above, which appears when you add a song to your Up Next queue but play a different song.

Features

iCloud integration works similarly to how it does in the latest iBooks app for iOS. All of the items you’ve purchase from the iTunes Store show up with a cloud icon on the corner of their artwork, and you can either download them or stream them. Streaming music has a slight delay while it buffers, but it’s not much more than Rdio or Spotify. Streaming a movie has a slightly longer delay of course, but not too long. Downloads are quick as well, and there’s a new downloads button in the toolbar that opens the downloads window. Yes, window, not popover. It doesn’t work like the downloads popover in Safari, which is a shame.

The new MiniPlayer is fantastic. You can search through your songs and manage your Up Next queue, which is all you really need if you’re just playing music. If you click on the album artwork on the MiniPlayer, it’ll pop out into its own QuickTime-like window. You can hover over the artwork to access playback controls, so you can use it as a desktop widget.

The new iTunes Store layout takes cues from it’s iOS counterpart. You can swipe to go back and forward in your history, but it doesn’t animate the way it does in the Mac App Store, which is strange. There’s also a new button to show you what previews you’ve listened to. You can share things in the store on Facebook and Twitter, which unfortunately open up web apps and not native OS X share sheets. It’s weird that I have to go an album’s iTunes Store page to share it as well; you can’t do it by simply right clicking on it.

There’s a new feature called Up Next, which replaces iTunes DJ. If you right-click on a song or album and hit “Play next”, it gets added to your Up Next queue. A new button in the playback panel shows a popover with your Up Next queue. You can also show your playback history by clicking the clock icon. iTunes DJ fans might be a little miffed with the update, as Up Next lacks some of its functionality, such as the ability for iOS users to vote on upcoming songs with the Remote app.

The AirPlay popover has been updated, and now allows you to play to multiple devices at once, which is nice. That’s it for new features. All of the old features, with the exception of Ping, are still there.

The little things

• Playlist management has been tweaked: When you start dragging a song, a panel slides from the side showing you your playlists. You can then just drag the song to the playlist to add it.
• The iTunes icon has been slightly updated, with a white double eighth note instead of a black one. It better matches the App Store icon, but there are still small differences between the two. The iTunes icon is a little glossier, and the double eighth note has a slight gradient to it. I like it better than the old icon, but I still dislike it overall.
• If you unhide the sidebar, you may notice that the icons in it have color, as oppossed to the greyscale icons in iTunes 10. Maybe we’ll see colored icons in the sidebar make a comeback on OS X?
• There’s a new “On This Phone” tab when managing an iOS device. It’s a simple view of all the media on the device.
• When you’re doing multiple things, like playing a song while syncing your phone, arrows show up in the playback panel that let you switch which activity’s progress is shown.
• You can no longer use a dark background in Album view, like you could in iTunes 10. Bummer.

Wrap up

iTunes 11 is the best version yet. Hiding the sidebar and status bar was a good move, removing a lot of the visual clutter that made iTunes feel complicated. Expanded Views are fun, and enhance the music listening experience.  The MiniPlayer is more powerful, and actually worth using now. All of this adds up to an iTunes that’s modern and fast.

The only thing holding iTunes back is the buying experience itself. With subscription-based services like Rdio and Spotify, you pay a monthly fee and get à la carte access to media without the hassle of having to buy it first. Finding music feels easier on Rdio because I’m only deciding whether it’s in my collection, not whether I want to buy it. There have been rumors that Apple will move to a subscription-based model for the iTunes Store, and I hope they’re true. As usual, we won’t know for sure until Apple makes their move. Until then, the new stuff in iTunes 11 will have to hold us over.

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But the tweaks to the service are going to be very welcome to many. iTunes 11 gets a bit of a makeover on its surface and under the covers to make it look more like the mobile version of iTunes that sits on your iPhone and allow content to better integrate with other Apple devices.

The user interface is revamped with more focus on album cover art and contextual information like the upcoming songs in your queue. The iTunes Store will have personal recommendations for users, artists will have their own dedicated pages on which they can share photos and tour dates with fans. The mini player also has a new look, and the software is more tightly integrated with iCloud: With iTunes 11 users can start watching a video on their Mac in iTunes and pick it up later on an iPad or iPhone in the same spot, and any music, movies or TV shows purchased in iTunes on another device can be re-downloaded from iCloud on the desktop.

For a neat look back at how iTunes’ design has evolved since 2001, be sure to see the retrospective that Ars Technica recently put together.

Update: MacRumors picked up on a cool new previously unannounced feature: you can now redeem gift cards or free codes for the iTunes Store via your computer’s camera.

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Apple first announced iTunes 11 at its iPhone 5 event in September, with Apple SVP of Internet Software and Services Eddy Cue saying at the time that it would be released some time in October. However, iTunes was notably absent from the company’s iPad mini event last week, leading to speculation that the development of the media player was behind schedule.

The new version of iTunes is supposed to feature a completely revamped user interface with a bigger emphasis on cover art, contextual information and dedicated artist pages that can be used by musicians to share photos, tour dates and other information. There were rumors earlier this year that Apple would integrate its own Pandora-like streaming radio service into iTunes, but recent reports indicate that this won’t be happening until next year, if at all.

The delay of iTunes 11 isn’t just notable for the digital media space; our own Om Malik reported yesterday that sources within Apple have been telling him of a shift towards a more schedule-driven product cycle. This has supposedly lead to the half-baked release of Siri and Apple Maps. The announcement of a software like iTunes before it was ready to be released could be another indicator of an increasing pressure to deliver on schedule. Then again, delaying the release could be seen as a sign that Apple is trying to avoid any further Maps-like debacles.

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The next version of iTunes is getting a pretty dramatic makeover, according to a brief report published Wednesday evening by Bloomberg. The changes will reportedly be the biggest the software has seen and will be implemented before the end of the year.

There aren’t a lot of details regarding specific changes Apple will make, but the few that are detailed are telling:

The company will more closely integrate its iCloud file-storage service with iTunes so users can more seamlessly access and manage their music, videos and downloaded software apps across different Apple gadgets, the people said. Apple also plans more features for sharing music, the people said.

So Apple is going to integrate iTunes with iCloud. That makes sense: Apple has made it clear that iCloud is a core company strategy “for the next decade.” But it’s also clear that Apple doesn’t really have a choice. It has to move iTunes into the cloud and into the future to more fully embrace its post-PC worldview.

iCloud is just over a year old and in that time it’s come a long way. Customers have signed up for it — 125 million so far — and Apple has been integrating more products into it. Last year it introduced music, photos, contacts, mail and calendar syncing, and iTunes Match with iCloud. At WWDC this year Apple says iCloud will be integrated with its browser, Safari, Documents and apps in forthcoming OS X Mountain Lion, and it beefed up Photostream sharing features. Apple is methodically expanding iCloud to its product lineup — iTunes is just one of the next products on the list.

The competition is also something Apple has to be keeping an eye on too. Amazon and Google are both coming for it with their cloud-based content services. Google showed on Wednesday that it’s starting to get serious about going after Apple’s iTunes strategy, by adding movies, TV shows and magazines to its Play store.

Plus, iTunes is aging and could use a good polish. It started as a place to discover and buy music, but Apple’s continued to tack services onto it over the years: it’s no longer just a place to discover and buy music, but TV shows, movies, digital books, online learning courses, podcasts and, of course, the massive and successful App Store. This isn’t spelled out in the report, but it’s also worth wondering whether Apple will use this opportunity to make the software more manageable. Perhaps by taking a page from the iOS team, which has successfully been able to split apart Music, Videos, App Store, iTunes Store, iBooks and most recently, Podcasts, into distinct apps.

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