1769, originally in horse-racing, referring to races in which bigger horses were given more weight to carry, lighter ones less; from give (v.) + take (v.). General sense attested by 1778. Give and take had been paired in expressions involving mutual exchange from c. 1500. Give or take as an indication of approximation is from 1958.
1910, originally theater slang for lower-salaried circuits, or ones requiring more daily performances; from noun phrase (also 1910). Compare big time.
"upper reaches of a profession or pursuit," by 1909 in vaudeville slang. As an adjective by 1915. The same phrase was common in colloquial use late 19c.-early 20c. in a broad range of senses: "party, shindig, fun, frolic."
"to deceive, cheat, betray," 1924, perhaps from notion of "to have two at a time." An earlier reference (1922) in a Kentucky criminal case involves a double-cross or betrayal without a romance angle. Related: two-timing (adj.); two-timer.