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(1) -- A shady male character who has a decieving smile, à le chat Cheshire. (2) -- A questionable song that sounds charming but at the same time, seems to have darker meaning. (3a) -- An uber-slick gentleman with a too-enthusiastic smile. Often the gent is hyper-sexual, or enjoys violence. (3b) -- A Cheshire dandy can also be known by other names, as long as Cheshire accompanies the insult/phrase used. (4a) -- Old-timey charm mixed with provocative intent. (4b) -- Cheshire can also be used on its own to speak of a gent.
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