Drag is a performance of exaggerated femininity, masculinity, or other forms of gender expression, usually for entertainment purposes. Drag usually involves cross-dressing. A drag queen is someone (usually male) who performs femininely and a drag king is someone (usually female) who performs masculinely. Performances often involve comedy, music, social satire, and at times political commentary. The term may be used as a noun as in the expression in drag or as an adjective as in drag show.

The origin of the term drag is uncertain; it may date as far back as the Elizabethan era in England, where it was used to describe male actors playing female roles in theaters where cross-dressing was the norm. The first recorded use of drag in reference to actors dressed in women's clothing is from 1870. One suggested etymological root is 19th-century theater slang, from the sensation of long skirts trailing on the floor. Another possible origin is the Yiddish term trogn meaning "to wear", from the German tragen. It may also have been based on the term grand rag, which was historically used for a masquerade ball.

Men dressed as women have been featured in certain traditional customs for centuries. For example, the characters of some regional variants of the traditional mummers' play, which were traditionally always performed by men, include Besom Bet(ty); numerous variations on Bessy or Betsy; Bucksome Nell; Mrs Clagdarse; Dame Dolly; Dame Dorothy; Mrs Finney; Mrs Frail; and many others.

The variant performed around Plough Monday in Eastern England is known as the Plough Play (also Wooing Play or Bridal Play) and usually involves two female characters, the young "Lady Bright and Gay" and "Old Dame Jane" and a dispute about a bastard child. A character called Bessy also accompanied the Plough Jags (also known as Plough Jacks, Plough Stots, Plough Bullocks, etc.) even in places where no play was performed: "she" was a man dressed in women's clothes, who carried a collecting box for money and other largesse.

"Maid Marian" of the Abbots Bromley Horn Dance is played by a man, and the Maid Marians referred to in old documents as having taken part in May Games and other festivals with Morris dancers would most probably also have been men. The "consort" of the Castleton Garland King was traditionally a man (until 1956, when a woman took over the role) and was originally simply referred to as "The Woman".

Cross-dressing elements of performance traditions are a widespread and longstanding cultural phenomena.

The ancient Roman playwright Plautus' (c. 254–184 BCE) Menaechmi includes a scene in which Menaechmus I puts on his wife's dress, then wears a cloak over it, intending to remove the dress from the house and deliver it to his mistress. Menaechmus says: "Look at me. Do I look the part?" [Age me aspice. ecquid adsimulo similiter?] Peniculus responds: "What in the world have you got on?" [Quis istest ornatus tuos?] Menaechmus says: "Tell me I am gorgeous." [Dic hominem lepidissimum esse me.]

In England, actors in Shakespearean plays, and all Elizabethan theatre (in the 1500s and 1600s), were all male; female parts were played by young men in drag because women were banned from performing publicly. Shakespeare used the conventions to enrich the gender confusions of As You Like It, and Ben Jonson manipulated the same conventions in Epicœne, or The Silent Woman (1609). During the reign of Charles II (1660–1685) the rules were relaxed to allow women to play female roles on the London stage, reflecting the French fashion, and the convention of men routinely playing female roles consequently disappeared.