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You could write a script to do this if the site in question had a predictable way to display user pages (eg. myspace.com/username), and potentially use the response header to tell you whether or not the username was taken. However, this would be a hit and miss solution, and likely wouldn't work on a significant number of websites. This may be what checkusernames.com does -- it's probably how I would do it if I needed to.
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