The "50s to the 90s"--which is so laughably general, that's
four generations of music, if not more--had The Beatles and David Bowie and it also had The Monkees and Men Without Hats. We have the artists who it's funny to make fun of, like Bieber, and we have Jack White, we have Kanye West, we have Radiohead--and we
had David Bowie, he's a modern artist
today, have you listened to Blackstar, which openly tips its cap to Kendrick Lamar?
Twenty years from now, Bowie and Kanye will be spoken of in the same breath (and sure, that happens today, but that's by the people who pay attention), and that's fine. Great work is done today just as much, if not more, as it was in the past, and you're being That Guy and you should never, ever, ever be That Guy.