Know why cattywampus was trending last week?
a viscous liquid, Old English teoru, teru, literally "the pitch of (certain kinds of) trees," from Proto-Germanic *terwo- (cf. Old Norse tjara, Old Frisian tera, Middle Dutch tar, Dutch teer, German Teer), probably a derivation of *trewo-, from PIE *drew- "tree" (cf. Sanskrit daru "wood;" Lithuanian darva "pine wood;" Greek dory "beam, shaft of a spear," drys "tree, oak;" Gothic triu, Old English treow "tree;" see tree).
Tar baby is from an 1881 "Uncle Remus" story by Joel Chandler Harris. Tarheel for "North Carolina resident" first recorded 1864, probably from the gummy resin of pine woods. Tar water, an infusion of tar in cold water, was popular as a remedy from c.1740 through late 18c.
"sailor," 1670s, probably a special use of tar (n.1), which was a staple for waterproofing aboard old ships (sailors also being jocularly called knights of the tarbrush); or possibly a shortened form of tarpaulin, which was recorded as a nickname for a sailor in 1640s, from the tarpaulin garments they wore.
in tar and feather, 1769. A mob action in U.S. in Revolutionary times and several decades thereafter. Originally it had been imposed by an ordinance of Richard I (1189) as punishment in the navy for theft. Among other applications over the years was its use in 1623 by a bishop on "a party of incontinent friars and nuns" [OED], but not until 1769 was the verbal phrase attested. Related: Tarred; tarring.
To lose all one's money, esp in a gambling game: ''It's tapping me out,'' he says
[1940s+ Gambling; perhaps fr having tapped everyone available for a loan and found none]