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Sunset Boulevard for the win
Well, my Sunset Boulevard story With the Best Intentions has won something :-)
Admittedly it was only an amateur in-forum contest with a grand total of five entries, but I've entered quite a few of these Writers Anonymous contests over the years and rarely if ever won. (The feedback is generally along the lines of 'didn't really meet the terms of the challenge prompt', which is fair enough, as I tend to end up using them instead as prompts to pull out my finger and actually write one of the pre-existing story ideas that has been kicking around in my brain for a year or so...)
Admittedly it was only an amateur in-forum contest with a grand total of five entries, but I've entered quite a few of these Writers Anonymous contests over the years and rarely if ever won. (The feedback is generally along the lines of 'didn't really meet the terms of the challenge prompt', which is fair enough, as I tend to end up using them instead as prompts to pull out my finger and actually write one of the pre-existing story ideas that has been kicking around in my brain for a year or so...)