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Technology October 25, 2006, 9:43PM EST

Apple, Tear Down This Wall

As iPod turns five, it's time to rekindle the debate over music download formats and ask again whether iTunes is too restrictive

Success breeds many things. Envy is one. Contempt is another. And sometimes those attributes combine, and then things can get really sticky.

Which brings me to the latest effort to circumvent Apple Computer (AAPL) and the technology it uses to limit copying of songs sold on iTunes.

DVD Jon

In case you missed it, a 22-year-old Norwegian named Jon Lech Johansen, who has a long history of tangling with copyright protection technologies and the companies that build them, has figured out a way to work around Fairplay, the digital encryption Apple uses to prevent songs purchased on iTunes from being played on non-iPod music players and multiple PCs. Apple also uses Fairplay to keep music from being shared iPod-to-iPod.

Johansen, you may remember, years ago cracked the copy-protection technology used on DVDs. The effort caught the attention of Norwegian prosecutors and landed Johansen in court. DVD Jon, as he came to be known, was ultimately acquitted.

This time around, Johansen plans to turn his know-how into a business. He's set up a company in Redwood Shores, Calif., called DoubleTwist Ventures. The aim: Show others how to make their content playable on an iPod by wrapping it in Fairplay. The company will also help companies that make rival devices play iTunes music and video on their own players. It's not clear exactly how this will sit with Apple and its always busy lawyers (see BusinessWeek.com, 10/27/05, "iPod Nano Lawsuits: Who Wins?"). The company so far is mum on DVD Jon's doings.

But it's notable that Johansen's venture emerged during the week that Apple celebrated the fifth anniversary of the iPod, the linchpin of much of the company's financial and cultural success in recent years (see BusinessWeek.com, 10/23/05, "The Apple iPod Turns Five").

The iTunes Garden

The iPod-iTunes combination is the very definition of a digital walled garden, at least so far as commercially downloadable music goes. Sure, you can rip music from your personal CD collection into unprotected formats like MP3, even legally make copies for personal use. But when it comes to iTunes, there's no digital equivalent of buying a CD and taking it home, knowing it will work with whatever brand of CD player you have.

Songs you buy from iTunes won't play on your MP3 player from Toshiba (TOSBF), Samsung, Sony (SNE), SanDisk (SNDK), or anyone else. Well, they're not supposed to anyway. The fact is, you can burn the iTunes songs to an audio CD, then re-rip them as MP3s and make them freely available to any player you choose—not that I would advocate doing such a thing, of course. And there is one commercial download service that makes its songs available in unprotected MP3 files that work with all players: eMusic.com.

Others have been down this path with Apple before. RealNetworks (RNWK) brought a lot of attention to the inherent problems with Apple's approach with its Harmony initiative in 2004 (see BusinessWeek.com, 7/27/04, "For Apple, Harmony Is Off Key"). The idea was to make songs downloaded from Real's music store playable on an iPod. Real and its CEO Rob Glaser took a lot of heat for the effort from irritated Mac and iPod fans, and Apple itself, which branded the move a "hacker tactic," but to this day, songs using the Harmony technology will still play on an iPod.

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