I've been saying that working in web feels like 1999 again, and that was true when I recently attended the Digital Music Conference in Los Angles. Overall, I was surprised that the vibe was still about "consumers are stealing our music" and "how can we enforce DRM?" and hadn't evolved more into forward thinking around revenue models. I'll go out on a limb here and say that there haven’t been many great recent progressions in online music with the exception of iTunes... and if we're honest - who doesn't miss the old Napster? Napster was brilliant in its sheer ease of use and depth/ breadth of selection.
There are a few lights on the horizon:
Spiral Frog which launches in December promises to be a free source of over 1 million legal music downloads. So far two large labels have signed on and they will take a cut of the advertising revenues. It promises to be a whole new paradigm on music downloads - if its successful I predict it will also influence video and other media downloads.
Rehearsals.com has fabulous "live" music content from established and emerging artists. They have state of the art rehearsal space in LA where they film musicians rehearsing and then stream it over the web. Powerful because this is exactly the kind of real, unedited music content that fans want to see! For the musicphiles, Rehearsals.com facilities are impressively high quality - with HD filming and unbelievable audio quality. This is definitely a company to watch!