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At one time, anyone could win a Golden Web Award no matter how their site looked, and there was no fixed limit on how many awards were given. The Addy awards, however, seem to be limited to three per city for a particular category. I believe that most clients won't recognize what an Addy award is, but I see more than a few people throwing its name around lately. So is the Addy even worth applying for? Has anyone here won an Addy and have a positive response from mentioning this to clients?
Having said that I wouldn't simply apply for any award, but rather one with some name recognition and a bit of credibility associated with it. Then for clients or in my proposals I would simply state "Award Winning Web Developer" without naming the award or when I received it.
Some will think this is silly and it probably is, but if it impresses even one prospect to the point of hiring me instead of my competitor or paying my asking price instead of hiring the cheap high school kid down the block than it was worth every bit of the effort or money it took to get.