Never understood how on earth someone like Bob Dylan could make it as a musician, let alone become legendary. But he did. He connected with his fans, and even though the quality of his singing voice sounded more like PeeWee Herman with a head cold than Sinatra - obviously a large segment of music lovers appreciated both his style and the uniqueness with which he sang. Although I personally struggle to appreciate his acoustical qualities, I nevertheless respect the manner in which he found a way to do his own thing, and in the process his ability to appeal to a generation of music lovers who found that connection enjoyable and entertaining.
I have an eclectic taste in music, and as a result I've learned to appreciate the things that make each performer different. Just a few months back we were remembering Prince's career and most all of the responses were incredibly favorable, as well they should've been. He was a fantastic singer/songwriter as well as an extremely talented instrumentalist, a true savant who left a legendary footprint that no one will ever duplicate. Part of that image however, whether one wants to admit it or not, was his outlandish costumes that would've made any haberdasher drool. The same could be said of Freddie Mercury. Or Madonna. Or Michael Jackson. Or Elvis Presley.
But when you listen to the music on the radio - you're not distracted with how they're dressed or what sort of costume they're wearing or whatever fashion statement they're trying to make. You're listening to their music, their voice, their ability to connect to the listener. And you either appreciate that type of music and the way they sing the lyrics and make that connection, or you don't.
Only you know what your musical tastes truly are, what qualities you appreciate most when you listen to someone's music. Which, in your case, doesn't mean you're either right or wrong. It's your opinion.
But where you are wrong is assuming that some music lovers are shallow enough to not be able to distinguish between fashion statements/lifestyle choices and a quality voice and musical style that they find appealing enough to download for $9.99 on iTunes.
When someone/anyone can sell over 100 million records, the last thing that comes to my mind is mediocre talent. I'm gonna go out on a limb and wager that it wasn't just about the way he dressed or his fashion sense. There was certainly more substance there than that.