Some fun homework: working from the following list, take note of the ones that are multiple-decades old, yet still on the list. Also take note of the noobs. Make a mental bet with yourself regarding which parts of that list will look very different 10 or 20 years from now, versus which artists will still be on it. Compare notes with yourself 20 years from now.
http://www.billboard.com/articles/li...-the-rich-list
Just a side note, I'd probably rather do prison time than listen to Justin Timberlake's music, but I am fully aware of the difference between personal musical preference and talent recognition. The guy is actually massively talented. I watched him on Saturday Night Live, and realized he has a very broad skillset that is spread across "pop music", dancing-boy-band-stuff, but more importantly to me he is reasonably good at comedic acting. Do not misunderstand me for a minute I respect the guy. He is very good at what he does. But what he does is spread so thinly across so many different media types that to compare him to some of the musical artists I've named in this thread is an absolute fucking joke. I think he is a smart enough guy that he would probably agree with me. He is not trying to be the next Tom Petty, he is trying to keep his cheese-mug in the limelight as long as can. Nothing wrong with that. He is making a shitload of money doing it and I do respect that, but a music legend he is not. Obviously he understands this, unlike his fans. That's why he is diversifying and trying to get into acting (or already has I guess).
But the bottom line is that if you're making a few dozen-million and still trying to figure out which skill you're best at, you're probably not one of the greatest musical talents of all time. Maybe overall performer? Social Media Icon? Paparazzi Bait? Perhaps. Not musical talents though.