Interesting discussion going on here! You're totally making sense SleepinIn.
I think the majority of artists are actually not going for the "shocking" aspect of things. I don't know, I guess if you need the shocking it's like you don't really have anything else to offer? I know that's probably not true, but still I find that trying to shock people is not really creative. Yes, you can try to wear the weirdest bra ever or sing a song about a threesome, but it's kind of just an easy way to get people's attention. Yes, if you have real talent in addition to the "shocking" aspect, it will lead to great success, like Madonna (not that I find her that talented, she can barely sing live, but I think she's very smart) and Lady Gaga. Or if you have a good team, like I bet Britney has, because seriously, at this point, I don't what she really has going for herself. But in the end, I still prefer those who can wow you with the creativity in their music instead of with any of the superficial stuff that we see too much of today (IMO of course). I guess it's all a matter of personal preference in the end.
Also, I think a lot of people might believe that the shocking aspect is literally tied with success in today's industry. People don't buy as much music as before, so I guess getting the music buyers's attention by any means possible is a reasonably good way to try to get some success. And you'll get more attention if you sing about kissing a girl or if you wear costumes than anything else.
Sorry, I'm probably babbling now.