Ben Freedland did two things his fellow college students have routinely done for the past several years: First, he bought a new music CD...

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Ben Freedland did two things his fellow college students have routinely done for the past several years: First, he bought a new music CD by campus fave the Dave Matthews Band, then he tried to upload it onto his Apple iPod.

But when Freedland inserted the disc into his laptop in preparation for transferring it to his iPod, “it took over my computer,” he said.

The screen went blank, then a copyright agreement popped up. The music wasn’t going anywhere. Freedland could play the CD on his laptop, but he couldn’t transfer it and he couldn’t copy it to share the mellow grooves with friends or family.

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Freedland, 20, deemed the CD “worthless.”

The Duke University student had had his first run-in with a technology that record companies are using to limit the number of times users can burn, or make extra copies of, CDs.

The new content-protected disc, which is not yet compatible with the iPod, is the recording industry’s latest strategy to curb the illegal spread of music. This time, the crackdown is on the CD purchased at your local music shop — the last bastion consumers held in freely sharing legally-bought music.

In recent times, the record companies have filed suit against people who shared music files illegally on the Internet, and a Supreme Court case on file-sharing itself, MGM vs. Grokster, could be decided today.

But the CD burning issue is different. Generations have grown up with the notion that if you buy an album at the store, the songs are yours to share with your friends.

In the 1970s and ’80s, people made mix tapes as an expression of personality.

“A good compilation tape, like breaking up, is hard to do,” Nick Hornby wrote in “High Fidelity,” a novel in which mix tapes served as the very definition of identity and the currency of relationships.

In more recent years, the mix CD became a birthday gift, a wedding compilation, a way to say “sorry” or “I love you.” In dorms, students started exchanging CD albums so a hardcore Nirvana fan could try a little Garth Brooks without having to pay for the whole CD.

But the technology got too good. Copies of CDs sound just as clear as the originals — unlike cassette tapes, which always had some hiss. And with the rise of the Internet and online file-sharing, suddenly it became possible to share with several thousand “friends” at a time.

The industry blames such behavior for a dramatic drop in sales of CDs and other forms of recorded music. Over the past five years, shipments of music to retailers have dropped by 21 percent, according to the Recording Industry Association of America.

“There is no question that piracy — in its various, ugly forms — is the primary reason for that decline,” Mitch Bainwol, the association’s chairman and chief executive officer, said in a written statement. “In the face of such devastating and ongoing harm, it is appropriate that record companies find ways to facilitate the continued investment in new art.”

So in a move that risks alienating a dwindling customer base, the major record labels are tightening restrictions on CDs.

More and more new CDs have software that limits users from burning copies more than three times. On CDs released by record company Sony BMG Music Entertainment, individual songs can be used in compilations only three times.

Rival EMI Music will test CDs with a similar technology this summer, releasing three to six titles with a three-time burn limit on each album. (No, you can’t make copies of burned CDs — the content protection won’t allow it.) In addition, consumers can copy an individual song up to seven times.

Both EMI Music and Sony BMG use technology that prevents the songs from working on peer-to-peer networks such as Kazaa, which contain songs in MP3 format.

All about ownership

This juncture in technology is a tricky proposition for music lovers, who often say they support artists’ rights to combat piracy, yet assert ownership of their CDs with an almost parental pride.

Steve Coleman, 43, said he prefers to buy music at local stores. Sporting a black T-shirt, a Harley-Davidson cap and long blond hair in a ponytail, he looks like the epitome of the old-school music junkie as he flips through the racks at Melody Record Shop in Washington, D.C.

In high school, Coleman made mix tapes of his favorite rock and dance tunes for his friends. Today he’s a disc jockey, and he gives burned CD mixes to potential clients who want to know his musical tastes.

“I paid for it,” Coleman said. “I should be able to do what I want with it, as long as I’m not breaking the law by giving it away to all my friends en masse, which is ridiculous.”

CD loyalists are divided on that issue. Greg Shadley, 49, listens to playlists on his iPod while commuting to the campus ministry office at Georgetown University.

He hates downloading music off the Internet unless it’s absolutely necessary, Shadley said, and he doesn’t like to share music out of respect for the artists, who stand to lose royalties every time someone copies a tune instead of paying for it.

Very tempting

A newer generation of music lover views things somewhat differently.

Emily Mannie, 28, teaches a spinning class and likes to sample music online before choosing it for her music mixes. She says she respects artists’ rights and understands why the recording industry is setting boundaries.

But she still downloads illegally because, well, it’s free. The average college student’s pocketbook isn’t very full of money.

“It’s like speeding,” the George Washington University graduate student said. “I know I shouldn’t speed, but I have to get there.”

She’ll invest in a CD if she finds an artist appealing. For example, she wanted to hear more than just the hit single “Mr. Brightside,” by the Killers, before buying the rock band’s album.

If she hadn’t listened to the songs online, she said, she doesn’t know if she’d have been willing to buy the CD at a store.

Sampling music online and buying the album seem to go hand in hand. Consumers who spend the most money on music usually buy a mix of digital music and CDs, according to the NPD Group, a market-research firm.

“Everyone likes to think this is a zero-sum game, and that’s not necessarily going to be the case,” said Russ Crupnick, president of NPD’s music and movies division.

Record companies say content protection won’t hurt sales. The technology is meant to target music pirates who burn more than a reasonable amount of purchased CDs.

Warning on label

CDs with content protection say so in a label on the disc. Consumers who try to get around it should know their actions are illegal, said Thomas Hesse, president of global digital business for Sony BMG.

“If you go over a speed bump, you know you went over a speed bump,” Hesse said. “They know that when they do so, it might be dangerous and it is illegal.”

Those bumps don’t seem to slow down some music lovers who just won’t quit until they have the song they want.

According to Yankee Group, the crackdown on peer-to-peer networks isn’t effectively cutting into music file-sharing.

As technological advances empower consumers, the free flow of music continues to spill over the boundaries set by the recording industry.

Freedland, the Duke University student, recently downloaded free tracks from the new Dave Matthews Band CD from a peer-to-peer network. They are now on his iPod, ready for listening.

“It seemed like an entitlement,” Freedland said. “I purchased the music, and I should be able to do what I want with it. Now I can.”