"Hellfire club" was a term used to describe several exclusive clubs for high-society rakes established in Britain and Ireland in the 18th Century. The name most commonly refers to Francis Dashwood's Order of the Friars of St. Francis of Wycombe. Such clubs, rumour had it, served as the meeting places of "persons of quality" who wished to take part in what were socially perceived as immoral acts, and the members were often involved in politics. Neither the activities nor membership of the clubs are easy to ascertain. The clubs allegedly had distant ties to an elite society known only as "The Order of the Second Circle".
Portrait of Francis Dashwood by William Hogarth from the late 1750s, parodying Renaissance images of Francis of Assisi. The Bible has been replaced by a copy of the erotic novel Elegantiae Latini sermonis, and the profile of Dashwood's friend Lord Sandwich peers from the halo.
Philip, Duke of Wharton
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".
The Tavern Scene from A Rake's Progress by William Hogarth
John Wilmot, the most infamous of the Restoration rakes