iTunes is Web 2.0ish in this sense. Finally you can buy individual songs instead of having to buy whole albums. The recording industry hated the idea and resisted itas long as possible. But it was obvious what users wanted, so Apple flew under the labels.  Though really it might be better to describe iTunes as Web 1.5. Web 2.0 applied to music would probably mean individual bands giving away DRMless songs for free.Paul Graham
Notice that this is one big monolithic corporation taking over the turf of other big corporations. In the old days, it would be iTommyGuns.
If you are on the production side of music instead of the consuming side, you notice that the last sentence is right precisely and only because iTunes will sell you individual songs, BUT they don't accept songs from individual artists.
Good for you. However, those hoping for freeing the artists from groveling to the record labels take note: now they grovel to Apple or one of Apple's designated MiddleGuys.
That's right. If you are an independent artist who wants to get a few shekels for your work and you see iPods as the new transistor radio, take note of Apple's policies: artists deal with middleGuys who deal with Apple. The middleGuys only deal with artists who make CDs (no submission of individual tunes) and have representation in the form of a label that represents many artists and they do this for tadaaaa: a percentage. Now I ask you, as iTunes proves, why should we be making CDs when they are selling individual songs?
Qui bono? The guys in the middle taking the bite are also selling CDs. And taking a bite. The artists, ahem, the labels still have to produce CDs and kids, that ain't cheap.
So that's Web 2.0 for the artist: the bad old business model reconstituting itself on the web and Apple making sure that happens. Volitionally. Good guys? Think again. These are business people with a market to conquer. Apple and their "contributors" take lots of little bites making one big bite into the product with no value added but to say 'yes'.
Umm... excuse me but that is exactly what we were doing before the web, during the web, and now Web 2.0 comes along to tell us no 'natch for the content makers without representation. Wow. Some victory....
So for you dweebs out there dwelling on how good it all is, Web 2.0 is good for programmers, venture capitalists, and people who believe the cost of software should be an item on their phone bill. Big artists are still a product of marketing. Street musicians and garage bands are still street musicians and garage bands. The only real improvement is they can pick the corner. The cost of recording is time and a few thousand bucks for gear. So sure, the good artists can record cheaper but that is about it. They are still on the street, on their own, out of luck and out of the money.
So if you pass one of them, toss a few coins in the hat and they'll toss back a few DRMless mp3s which by fact of having given them away, reduced their economic value to zero.
So artists are what they always were: meat. Smart ones build their own Web 2.0 web sites and have Paypal or its ilk anyway. The rest of us do it for boo.
What does Web 2.0 mean? It means exactly what the market always means: the same people get to make money again for the same software except this time it will be cheaper, come in smaller boxes, and do less than it did last time which means you will buy/download/subscribe to more to get the same. But this time, when it gets obsoleted, you will change like it or not. You may not notice, and you won't have to hunt through your old CDs for the backups but if you lose your credit card number, it won't matter anyway because they don't know your name, just your credit card number.
The Web 2.0 is the next version of progress for the same reasons for the same people: items based on scarcity may not be interesting to investors, but scarce capital is everyone's problem. The ownership society never acknowledges that and that is Graham's social network.
"All the gold in California is in a bank in the middle of Beverly Hills in somebody else's name..." The Gatlin Brothers.