Old English twentig "group of twenty," from twegen "two" (see two) + -tig "group of ten" (see -ty (1)). Cognate with Old Saxon twentig , Old Frisian twintich, Dutch twintig, Old High German zweinzug, German zwanzig. Gothic twai tigjus is even more transparent: literally "two tens."
The card game twenty-one (1790) is from French vingt-et-un (1781). Twenty-twenty hindsight is first recorded 1962, a figurative use of the Snellen fraction for normal visual acuity, expressed in feet. The guessing game of twenty questions is recorded from 1786.