Writing and art prizes - I don't get that entire subculture. Maybe it seems natural to those who are a part of it. From the outside it looks like a game of
duck, duck, gray duck around an academic campfire.
Anyway, if a Bukowski award for literature were to be established, it would have to be established by the people who control the Bukowski name as it's used in the lit world (i.e., Linda B. and/or HarperCollins).
To my mind, Bukowski significantly changed the way poetry was written. A prize in his honor should go to someone who achieves something similar. Such a prize would be given out very infrequently. ;)
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The idea of micro-grants is interesting though.
This guy gives out $200 - $300 grants (based on one night of his tips working as a waiter), which is a pretty cool idea. It's not Nobel-Prize-change-your-life kind of money, but any check is a good check as far as I can tell.
Establishing and managing something like that requires real world commitment though. As Father Luke's "just do it" suggestion illustrates, talking about it in a forum is one thing, actually making it happen is something else. If you are passionate about a Bukowski prize, start it up. Use his name with impunity and let HC/Ecco sue you. ;) Spit in the face of the literary establishment!
We all do our own thing to subvert the status quo. Or we don't.