The best thing about the internet age and generational shifts is no longer having to be embarrassed about loving Weird Al. Or maybe more accepting attitudes toward the marginalized. But one of those.
I don't think I've heard a Weird Al song since "White and Nerdy" (which is pretty great). Weird Al has always been interesting to me. I've seen reddit stories that he's very professional, and that he always asks permission before using a song. Most artists are flattered if he picks their song. Considering what his persona is for a career, by all accounts seems to be pretty cool.