The thing is, I don't think there are any young music afficionados who would honestly claim that they can see the next David Bowie out there right now. Or seen anyone coming through over the past 10 years or so who would even run him close. I get the impression that people like him are still held on a pedestal, no matter what generation you're from.
It's as though there was a golden era of popular music in the 60s through to the 80s, with a gradual decline since. Radiohead probably being the most recent band who can make any claim to greatness on a truly global scale, with no obvious successor waiting in the wings. Obviously, the talent is out there but for various complicated reasons they're not being given the money or artistic freedom needed to produce a truly great piece of art. Could be wrong though. Be interested to hear some thoughts from young 'uns.
Music in Britain since the 60s has had two occasions when the fundamental model of how the music worked changed. The first was in the mid to late 70s when punk happened, the next was in the late 80s when acid house landed.
As well as sounding sonically different to what went before, the very nature of the industry changed. It changed the very paradigm for how music is created, which in turn had an impact on how the music sounded. It wasn't simply different chords or lyrics. How it was made and consumed changed.
Previously a small number of talented people produced the music that was consumed by many. Bowie, Beatles, Stones, Dylan, etc. However punk subverted this concept with the notion of DIY. This wasn't some elitist activity any more, it was something anyone could do if they got together with their mates. It liberated music. In terms of talent it was incomparable to the great singer songwriters, but that wasn't the point. The point was that this was the music of the masses. It was the quantity produced, not its quality. It was democratic.
The trouble is you still needed a set of instruments, you still needed to play gigs and you still needed a record deal. So it petered out.
Then the trick repeated when acid house landed. This time it was even easier, you could write music in your bedroom alone, you didn't need any musical talent, you didn't need to be good looking, with a good voice or confident on stage. At this point the concept of DIY music stuck.
The most interesting example to date came with the birth of british hardcore (old skool) in the early 90s. You had a situation where one person would write a track with some essentially arbitrary motif - a particular noise, a childs cartoon sample, a notable drum sound - then upon hearing that dozens or even thousands of people would write rip offs of the track in their room the very next day. The following week all those tracks would be played in clubs and raves up and down the country, and each one would produce a spin off. To put the scale of it in context, I personally have about 20,000 old skool tracks from 91 to 94, and I doubt that's even 10% of what's out there. It really was music creation on an unprecedented scale.
And so like any system, ultra rapid reproduction and rebirth set about a process of musical evolution on an accelerated timescale. It also created a parallel paradigm for how music can work within a scene. As well as than one talented person or band pushing boundaries, thousands of people contribute to the evolution of the music which moves in a seemingly random, homogenous fashion. The quality within the musical genre comes not from what one person can do, but where the collective goes.
The last piece of the puzzle was mp3s and particularly iPods. Before those, the only way to digest that much music was at clubs or on the radio. However they allowed people to carry the 20,000 tracks of their choice with them. That eliminated the final barrier stopping that type of musical paradigm from being easily digestible by the majority. Indeed since then the various new digital techs has if anything sped the whole thing up.
Music can be thought about in more ways that just sonics. When you think about it the biggest change in the history of music was almost certainly when music could first be recorded and replayed, which only really took place in a meaningful way a hundred years ago. In the same way post-modernist art was ushered in by the ability to reprint pictures, musical change was propagated by that same ability to reproduce. The next biggest change for me was the re-democratisation of music in the 70s and 80s, with musical worth being measured by the movement of the many, rather than the talent of the few.
So we may not get people doing what Bowie did again. The conditions aren't right for it. However if you look past a talented bloke making good tunes and consider the spectacular change in music evolution in the post-war era I would argue that we're just now entering a golden age of music, the inevitable logical conclusion of recorded music.