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In a historical context, a rake (short for rakehell, analogous to "hellraiser"), was a man who was habituated to immoral conduct, particularly womanising. Often, a rake was also prodigal, wasting his (usually inherited) fortune on gambling, wine, women and song, and incurring lavish debts in the process. Comparable terms are "libertine" and "debauchee".

The Restoration rake was a carefree, witty, sexually irresistible aristocrat whose heyday was during the English Restoration period (1660–1688) at the court of Charles II. They were typified by the "Merry gang" of courtiers, who included as prominent members the Earl of Rochester; George Villiers, 2nd Duke of Buckingham; and the Earl of Dorset, who combined riotous living with intellectual pursuits and patronage of the arts. At this time the rake featured as a in Restoration comedy.

After the reign of Charles II, and especially after the Glorious Revolution of 1688, the cultural perception of the rake took a dive into squalor. The rake became the butt of moralistic tales in which his typical fate was debtor's prison, venereal disease, or, in the case of William Hogarth's A Rake's Progress, insanity in Bedlam.

The defining period of the rake was at the court of Charles II in the late seventeenth century. Dubbed the "Merry Gang" by poet Andrew Marvell, their members included King Charles himself, George Villiers, 2nd Duke of Buckingham, John Wilmot, 2nd Earl of Rochester, Sir Charles Sedley, Charles Sackville, 6th Earl of Dorset, and the playwrights William Wycherley and George Etherege. Following the tone set by the monarch himself, these men distinguished themselves in drinking, womanising and witty conversation, with the Earl of Rochester outdoing all the rest. Many of them were inveterate gamblers, brawlers and some were also duelists but not to the approval of King Charles. Highlights of their careers include Sedley and the Earl of Dorset preaching naked to a crowd from an alehouse balcony in Covent Garden, as they simulated sex with each other, and the lowlight was Buckingham's killing of Francis Talbot, 11th Earl of Shrewsbury in a duel for the latter's wife. In 1682 Thomas Wharton, 5th Baron Wharton, broke into a church at night and relieved himself against the communion table and in the pulpit.

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