adj. Out of touch or ignorant.
It's rather silly that teen flicks are racking up huge box office numbers and Hollywood's acting like it's some earth-shattering phenomenon. Studio execs, you're so 404.
—“Gusto,” The Buffalo News, March 05, 1999
1995 (earliest)
Someone who's clueless. From the World Wide Web error message "404, URL Not Found," meaning that the document you've tried to access can't be located. "Don't bother asking him … he's 404, man."
—Gareth Branwyn, “Jargon Watch,” Wired, January 01, 1995
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