Rakish
In a historical context, a rake (short for rakehell, analogous to "hellraiser") was a man who was habituated to immoral conduct, particularly womanizing. Often, a rake was also prodigal, wasting his (usually inherited) fortune on gambling, wine, women, and song, and incurring massive debts in the process. Cad is a closely related term. Comparable terms are "libertine", "roué" and "debauchee".
The Restoration rake was a carefree, witty, sexually irresistible aristocrat whose heyday was during the Stuart Restoration period (1660–1688) at the court of King Charles II. They were typified by the "Merry Gang" of courtiers, who included as prominent members John Wilmot, George Villiers, and Charles Sackville, who combined riotous living with intellectual pursuits and patronage of the arts. At this time the rake featured as a stock character 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 debtors' prison, venereal disease, or, in the case of William Hogarth's A Rake's Progress, insanity in Bedlam.
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