On 24 May 1660, Samuel Pepys first encountered Thomas Killigrew among other ‘persons of Honour’ on the deck of the Naseby (hastily renamed the Royal Charles), which was bringing Charles II back to England at the end of his long exile. In his diary Pepys described Killigrew as ‘a merry droll, but a gentleman of great esteem with the King’.1 The ‘merry droll’ opinion would have been based on a firsthand assessment, as Killigrew entertained the shipboard company of uncourtly Londoners with ‘many merry stories’. The example recorded by Pepys was a farfetched and ridiculous account of how a courtier’s wife, who had previously been a nun, had impersonated at The Hague a queen of Judaea and Palestine and, in this guise, had made love to Charles II.2 How did Pepys know that the teller of these droll but outlandish stories was also ‘a gentleman of great esteem with the King’? Someone, presumably one of the courtiers or royal attendants among the returning exiles on the Royal Charles, must have told him. But how close was Killigrew to Charles II? What was his actual standing in the Restoration court? Was he anything more than just a ‘merry droll’, a kind of licensed court jester? And since, as a groom of the bedchamber to Charles II, he was well placed to be at the centre of court intrigues and politics in what has been called ‘the age of faction’,3 how did Killigrew’s career as an ambitious and enterprising but eventually financially unsuccessful theatre manager interrelate with his role as a courtier?