In a historical context, a rake was a man who was habituated to immoral conduct, particularly womanizing. Often, a rake was also prodigal, wasting his fortune on gambling, wine, women, and song, and incurring lavish debts in the process. Cad is a closely related term. Comparable terms are "libertine" and "debauché".

A libertine is a person devoid of most moral principles, a sense of responsibility, or sexual restraints, who sees these traits as unnecessary or undesirable, and is especially someone who ignores or even spurns accepted morals and forms of behaviour observed by the larger society. The values and practices of libertines are known collectively as libertinism or libertinage and are described as an extreme form of hedonism. Libertines put value on physical pleasures, meaning those experienced through the senses. As a philosophy, libertinism gained new-found adherents in the 17th, 18th, and 19th centuries, particularly in France and Great Britain. Notable among these were John Wilmot, 2nd Earl of Rochester, and the Marquis de Sade.