the phrases built on the pattern ‘to out-X X’, in which ‘X’ is a person’s name, mean to be superior to X in his or her characteristics—the prefix ‘out-’ has been used to form verbs conveying the sense of surpassing, exceeding or beating in the action described by the simple verb
informal and often humorous: denotes the explicit or most intimate details of something—originally (USA, 1859) referred to accounts or representations of acts of violence and bloodshed
UK, 1819—has been used in various jocular phrases referring to alcohol consumption—punningly alludes to ‘lush’, which, as a noun, denotes alcoholic drink, and, as a verb, means to consume alcohol—‘the City of Lushington’: a convivial society, consisting chiefly of actors, which met at the Harp Tavern, London
1907—whether one likes it or not; haphazardly—a humorous variant of ‘willy-nilly’, after the personal name ‘William’ (‘William’ being familiarly shortened to ‘Willy’)
UK—(used of a group of people) to keep passing the initiative or responsibility from one person to another, so that no action is taken—refers to a party game in which a gift wrapped in several layers of paper is passed around a circle of players to the accompaniment of music, the losers in successive rounds being those holding the parcel when the accompanying music stops
‘parting shot’ (1817); ‘Parthian shot’ (1822): a sharp, telling remark, act, gesture, etc., made in departing—‘parting shot’: literally the final shot fired at the moment of departure—‘Parthian shot’: refers to the Parthian horsemen’s habit of shooting arrows backwards while in real or pretended retreat
USA, 1843—With reference to a dog used for hunting game, this phrase is used to express the opinion that a particular plan or approach will not succeed.
USA, 1927—denotes male vigour, especially sexual—with wordplay on ‘penis’—interestingly, via an alteration of the Latin diminutive ‘pēnĭcillus’, denoting literally a little tail, hence a painter’s brush or pencil, ‘pencil’ is derived from Latin ‘pēnis’, denoting literally a tail, hence the penis
USA (New England), 1868—alternately sunny and cloudy conditions usually indicate rain—the adjective ‘shet’ is a variant of ‘shut’—it was perhaps in order to provide a rhyme for the adjective ‘wet’ that the variant ‘shet’ was chosen in the proverb