herb

Someone who tries more than anything to be cool, to the point of ironic backfire, because the person gets annoying, achieving a reputation for getting in the way and pretending to know everything but with an extreme lack of merit. As a result, trying so hard to be cool has the opposite effect, and one becomes a "herb" herb.

(in new york accent) "kevin yo' such a herb, yo' goin' to xavier, one uh da best private schools in da city and yo' failin' spanish.

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