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I haven't ever emailed a real celebrity, I mean, not a towering figure like Janis Ian (I don't mean that facetiously, to me she really is a true legend.)
But I have emailed a couple of cartoonists whose work I admire, and they answered me very graciously.
Edited to add: I emailed Warren Zevon (long before he died) and his son Jordan sent me a very nice reply. (I am and have always been a huge WZ fan.)
I emailed a couple indie film directors to tell them that I thought their movies rocked and now I'm email friends with both of them. I also emailed Adam Curry back in 1993 and we emailed back and forth for a lilttle while. He was on the forefront of the internet thing back then!
I've written to Kenny Rogers from MySpace site two years ago. Never heard back.
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