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I think the Distilled page is not an example to get inspiration from:
It's fun, it's a well cured page, I actually like it a lot, but inviting to report the error to an administrator is plain wrong (http://visual-seo.com/SEO-Blog/Silliest-Error-Message-on-the-Web)
The best 404 page I've ever seen is from my competitor Screaming Frog: http://www.screamingfrog.co.uk/seo-spider/notapage
It doesn't help you at all finding the content you were looking for, but nevertheless one couldn't resist staying on the site!It's not perfect, though.
Weirdly it doesn't capture all 404 cases: if you use a number as page name in a subdirectory, you are served 200 OK regular page; e.g. such link would lead to a duplicate content issues: http://www.screamingfrog.co.uk/seo-spider/404/
Thanks for your comment Federico! You bring up an interesting point about the distilled page and the reporting it to an administrator, or in this case the "web butler". I can't help but laugh a bit each time I read it though!
Thanks for bringing up Screaming Frog's 404 page, I've been playing Frogger for the past 30 minutes and cant get past the first level yet! haha