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Weird Al is indeed a fascinating phenomenon. Artists and acts like him are expected to be a mere flash in the pan, and there have been many before him and many after him that will be just like that. I can only assume that he struck that magical, fine balance between luck, hard work and sheer talent that makes him enduring. I liked the part about his creative process, and the way he exhausts lyrical possibilities . It's a strong reminder that parody is not an easy thing to do.
What struck me as really funny is the phrase that the "get over your ego" thing he does is a very American thing. I've lived 34 years in a country that's essentially the USA's backyard, I've gobbled up much more American influence and culture than is recommended by the WHO, and I can say there's nothing less American than egalitarianism. What I've learnt from the exhaustive bombardment of Uncle Sam nationalism is that we have to prove our worth and show what makes us unique, win first place in the school science fair, win that talent contest, fix our self-esteem problems and invite the pretty girl to prom night; and that all superstardom is deserved, it's a gift sent by God. If anything, the reason why mainstream culture embraces the parody act and the occasional satire is to give the fleeting impression that criticism is effective, and neutralising it at the same time. It's the reason why Deadpool exists: because he breaks the 4th walls and knows all the Internet memes, that makes Marvel "self-aware" and immune to all criticism, and all "roasting" is a form of post-ironic praise.
... and yet, all those things make Weird Al even more interesting as an artist, because he somehow stands above all the post-irony. I think it's exactly his sincerity that makes him different, so he has no need to be afraid of being reverent. He clearly admires the artists and songs he parodies, and that makes him bigger, not smaller.
And I still love him very much for Don't Download This Song.