On the theme of music, I loved this overview of the life and times of Weird Al.
As his name suggested, Weird Al’s comedy operated right at the hot spot of my childhood agonies: weirdness versus normalcy, insider versus outsider. What a Weird Al parody did was enact a tiny revolution. It took the whole glamorous architecture of American mainstream cool — Michael Jackson’s otherworldly moves, Madonna’s sexual taboos — and extracted all of the coolness. Into that void, Weird Al inserted the least cool person in the world: himself. And by proxy, all the rest of us weirdos, along with our uncool lives.
I wasn't a huge fan myself, but my childhood best friend sure was. We listened to a lot of those albums in the 80's, and quite enjoyed UHF (especially Conan the Librarian and Stanley Spadowski, masterfully portrayed by Michael Richards (aka Kramer from Seinfeld)).
But you don't have to be a fan of his music to appreciate Weird Al's influence and longevity.