I recommend Lets Talk about Love, a book by a music critic about getting over his trained-in hatred of Celine Dion's music.
This is the other side of the post-- I don't think there's a problem with enjoying popular music, or seeking out popular music to find out whether you enjoy it. There probably is a problem with letting other people teach you what music to hate.
Speaking of Celine Dion, I've found her songs to be widely inconsistent in quality... some I absolutely can't stand at all but there are others that I'm rather fond of.
I just downloaded the latest Radiohead album, and I love it.
Thinking back, I started listening to Radiohead years ago when I found out that some of the cool kids in school were into it. With all the hype about the new album, the status/fashion processors in my brain going to ensure that I enjoy listening to it. I would probably fail a double-blind test with a bunch of imitation bands' fake "new Radiohead albums".
But I'm really enjoying listening to the album, and that doesn't seem like a bad or contradictory thing at all, even in light of the statements above. If, hypothetically, I was enjoying it for purely non-fashion reasons, then presumably that enjoyment could also be traced back though a causal chain to facts about brain development, evolutionary psychology, or whatever. But we would have no problem accepting that enjoyment as A Good Thing since explaining enjoyment does not diminish it. And so it seems in this case.