I like Lady Gaga. As someone who grew up on Madonna's music, I think Lady Gaga is much more original and interesting. We'll see if she has the same staying power. Let's check back in another 30 years.
I agree generally about music. I guess what I've noticed more is that there hasn't been a big wave that defines a generation. Rock 'n Roll, Disco, Metal, Hip Hop, Grunge... I don't think a really new sound has come out since the mid 90s. The pop music they play today sounds exactly like the same stuff as when I was a teenager in the 80s. C'mon, I want to be shocked by what the youngsters are into!
I think something similar has happened in fashion. We've recycled the 60s, the 70s, and now the 80s. What happens now? We start on the 60s again?
I think with both fashion and music, genuinely new trends are pushed by technology, like mass production of synthetic fabrics. There haven't been any major innovations in either area for the past 20+ years. I think that's why stuff has been so, well. Boring.