The Digital-Music Mosh Pit

A new wave of Web innovation is finally challenging Steve Jobs’s empire of cool.

I had my music-geek epiphany early last year. Like many music heads, I’d been playing with the two best-known interactive streaming music services: Pandora and Last.fm. With either one, you enter your favorite songs and artists, and the service then streams back music you might like, operating on something of a this-may-look-odd-but-it-tastes-like-chicken principle. Each comes at the issue from a different angle, though.

Pandora is a wonderfully intuitive but only intermittently successful experiment in applying a “genome” metaphor to music: it breaks down hundreds of thousands of songs to their constituent elements—rhythm, melody, tempo, and so forth. It’s a cool idea, but the biology-based approach to music listening can turn into a farcical mashup of styles, in which a request for something similar to Grandaddy (a gentle, incontestably credible alt-rock band from Modesto, California) yielded me music that sounded like easy-listening classics from the 1970s. Pandora is, of course, correct that Grandaddy basically is Air Supply in indie drag, but an online seeker wants affirmation, not critique.

Last.fm takes the simpler tack of grouping music by what other listeners like—so if, for example, you key in the Austin, Texas, band Spoon, you’ll be told what other Spoon fans on Last.fm are into. And Last.fm, if you let it, will track what music you’re listening to and connect you to people who like similar music, a hallmark of “social media” or “Web 2.0” sites.

I’d long felt a profound sense of loss over the demise of the Mancunian band the Stone Roses, whose eponymous 1989 album raised rave-y Britpop to the level of sacrament. So I keyed in Stone Roses, expecting to hear the similar- sounding Charlatans UK or Kasabian, a current Roses-ish group. Instead, I was kicked back Neutral Milk Hotel, an Athens, Georgia–based collective centered around an artist named Jeff Mangum. NMH’s 1998 In the Aeroplane Over the Sea is a wildly over-the-top cult masterpiece, an operatic song cycle that probes the mystical import of the fate of Anne Frank and other tragedies. Take my word: it sounds only marginally like anything by the Stone Roses. But both albums are on my mental top-ten-of-all-time list, and I had flattered myself that only I saw the cosmic linkages between the two albums’ mystico-religious sound washes, rave-ups, and idiosyncratic lyricism. Having it recommended to me was a goosebump-inducing moment—and a neat demonstration for me of why social media is sweeping the Web: There are other people out there who feel this as deeply as I do! Maybe we can all get together and achieve a higher unity!

These are vertiginous, thrilling times for music fans. Where once my only options were CDs and radio, I can now deploy a battery of devices, platforms, and formats to enjoy the music I already own and to find more. Most of us are only now starting to unlock the potential of our iPods, but the pace of change in the digital-music sphere is such that even the pleasures of spinning the wheels on our nanos will soon seem old hat. As I’m writing this, I’m playing a Flash-based MP3 blog extractor called Hype Machine. It’s a simple Web-based application that sucks songs mentioned in music blogs into an Internet radio stream. I just heard a new Neil Young track segue into an awesome club banger by a rapper named Milano. Now it’s playing an electro-tastic Modeselektor remix of “Dial Zero” by My Robot Friend. Clicking on “read blog post,” I was taken to a blog named “ill-ec-tro-nic” that told me more about the track and others like it—plus where to buy it.

Hype Machine operates in a legal gray zone: it doesn’t technically have the rights to play this music, but argues that it is simply pointing interested listeners toward bloggers who post links to MP3s, themselves mostly operating in their own legal gray areas. No matter. From Napster onward, music has become a vast Schumpeterian mosh pit of legally dubious digital disintermediation, quick adjustments of economic models, and new leaps forward (or backward, if you’re the hapless music label, watching your intellectual property propagating, royalty-free, throughout the Web). That these leaps are happening in three-month increments, rather than the fifty-year cycles of classic modern economics, is testament to the wonderful insanity of this moment.

Indeed, a friend returning in early November from the Web 2.0 Summit in San Francisco reported that much of the conference buzz revolved around a new digital product called iLike, which turns the closed iTunes system into something very much like Last.fm (apparently without the blessing of Apple). Downloaded as a “sidebar” to my desktop, it automatically tracks the music in my iTunes library and finds fellow iLike members whose music tastes are compatible with mine. (It works on Windows as well.) Playing with the iLike beta recently, I entered my musical preferences through a handy thumbs-up feature that harvested my opinions on a range of well-known artists. Immediately, up popped the image and musical history of a young woman named “C,” whose affection for Regina Spektor, Massive Attack, and Shiina Ringo (no, I don’t know who that is either) marked her as being musically compatible with me. I was offered the chance to send her a “private message.” The subtext here, as with all of the most effective social-media sites, couldn’t have been clearer: sharing your peerless taste in music would not only get you status; it might also get you laid.

The iLike beta launched in late October. One can assume that by Memorial Day, if not by the time you read this, the heretofore social-media-unfriendly Apple will have launched a competing product, bought iLike’s parent company, or tried to sue the parent company into bankruptcy.

There is order to the madness. If you accept as an article of faith (and I do) that the existence of digital media means everything will eventually become available everywhere for a price that will approach zero, you can start connecting the dots. I’m currently faced with an arbitrary choice: if I want to walk around with my music in my iPod, I have to interface with the closed iTunes system and purchase songs at 99 cents a pop (or, for non-major-label offerings, go to eMusic.com); if I want to enjoy new music, learn about music from people who’ve built cool user pages, and generally share in the communal joys of critical discrimination, I have to leave iTunes and sniff about online. It is surely only a matter of time before that problem is solved. Indeed, a new peer-to-peer file-sharing service named SpiralFrog (backed by EMI and the Universal Music Group) is planning to offer free, advertising-supported download services. It will be portable but will not work with your iPod. (Kazaa, which recently promised to stop allowing illegal music and video downloads, is apparently also exploring a similar ad-supported service.) It’s unclear if this free music will work on the newly launched Microsoft Zune, which is trying to end-run the iPod by offering wireless capability. It allows users to share music files on the go with other Zune users who are within wireless range. This is less sexy than it sounds, since the music you share disappears after three days, and Zune’s other features, including its online digital-music store, offer no real advance over iTunes. Sales have been slow.

If past is prologue, SpiralFrog and Kazaa, too, will come up short. But all these failures are in the service of a dynamic evolution. Someone—and that someone is likely already at work on the key advance—will figure this out. One next step could be a move by the labels to make more pay-per-download music available without restriction, meaning that once you’ve purchased a song, you can do anything you want with it, currently a no-go on Zune or iTunes. Unrestricted MP3 sites could play VHS to iTunes’s Betamax. However it occurs, though, the execution of a widely used free and free-flowing music download and sharing system is surely imminent.

Is it possible to conceive of a moment when the iTunes/iPod system is no longer dominant? Like console games and cable and satellite TV, iTunes/iPod has been a stunningly successful execution of a closed, or “end-to-end,” system. The iPod is, obviously, a triumph of design, and it exploded onto the music scene because it offered reasonably flawless, intuitive execution (and, to the intellectual-property owners, flawless digital- rights management) at a time when illegal file sharing could not only crash your computer but destroy your hard drive. Yet it is also a triumph of ideology. Steve Jobs has successfully positioned Apple as “getting it,” damning the insufficiently Hipsterville Windows masses to lives of monochrome drudgery—the Mac-versus- PC TV ads being only the most blatant expression of Apple’s bid for a social conformity of ironic T-shirts, studiously asymmetrical coifs, and an iPod nano in the outside pocket of your Manhattan Portage messenger bag. Never mind that your $399 iPod video will not let you transfer music back onto your (or any other) desktop.

Apple also remains the beneficiary of a network effect that makes iPod’s nearly 80 percent market share self-propagating. Once you’ve sprung for the nano, bought the $3,000 computer to sync it to, downloaded $500 worth of music, purchased a Coach carrying case and a cool iPod camera attachment, bought the thingamajig that allows you to stream your iPod through your car radio, and watched your iPod video on an airline that offers it compatibility, you can barely conceive of decamping to an entirely different system with strange keystrokes and a whole new set of technical glitches.

Still, services like iLike and Hype Machine offer the first compelling conceptual challenge to Apple’s closed-end system, threatening to upend its virtual Williamsburg of cool. We are at a moment when the digital-music experience is moving from a linear to a dynamic model: the many telling the many what they like, hate, and want others to hear, and providing a communal experience that re-creates digitally some of the reasons we fell in love with music in the first place. This places Steve Jobs in the awkward position of selling the passing pleasures of dissociated loners moving about in their iPod bubbles when a musical carnival is breaking out all around him. (All eyes will, per usual, be on Jobs this month at the Macworld Expo, when he performs his annual product unveiling—rumors are of an integrated cell phone/iPod.)

As for me, I already find that I’m not missing my iPod, which recently broke, on cue, after only a few months. An office mate hooked me up with an iRiver Clix, an ingenious little two-gigabyte MP3 player that’s as functional as my old iPod—and actually gets stares on the subway. It syncs nicely (if laboriously) with my computer’s Windows Media Player, and suddenly I’m shuffling in and out of thousands of songs on the fly—including that Modeselektor remix of My Robot Friend.