His debaucheries and his riotous frolics were often the outcome of long spells of drunkenness. Towards the end of his life he declared that he was under the influence of drink for five consecutive years. At the same time he cultivated a brilliant faculty for amorous lyrics, obscene rhymes, and mordant satires in verse, and, although he quickly ruined his physical health by his excesses, his intellect retained all its vivacity till death.
The king readily admitted him to the closest intimacy. He was Charles's companion in many of the meanest and most contemptible of the king's amorous adventures, and often acted as a spy upon those which he was not invited to share. But although his obscene conversation and scorn for propriety amused the king, there was no love lost between them, and Rochester's position at court was always precarious. His biting tongue and his practical jokes spared neither the king nor the ministers nor the royal mistresses, and, according to Gramont, he was dismissed in disgrace at least once a year. It was (Pepys wrote) ‘to the king's everlasting shame to have so idle a rogue his companion’ (Pepys, viii. 231–2). He clearly exerted over Charles an irresistible fascination, and he was usually no sooner dismissed the court than he was recalled. He wrote many ‘libels’ on the king, which reeked with gross indecency, but his verses included the familiar epigram on the ‘sovereign lord’ who ‘never said a foolish thing and never did a wise one’ (‘Miscellany Poems’ appended to Miscellaneous Works of Rochester and Roscommon, 1707, p. 135). He lacked all sense of shame, and rebuffs had no meaning for him. On 16 Feb. 1668–9 he accompanied the king and other courtiers to a dinner at the Dutch ambassador's. Offended by a remark of a fellow-guest, Thomas Killigrew, he boxed his ears in the royal presence. Charles II overlooked the breach of etiquette, and next day walked publicly up and down with Rochester at court to the dismay of seriously minded spectators. When he attempted to steal a kiss from the Duchess of Cleveland as she left her carriage, he was promptly laid on his back by a blow from her hand; but, leaping to his feet, he recited an impromptu compliment.
On one occasion, when bidden to withdraw from court, he took up his residence under an assumed name in the city of London, and, gaining admission to civic society, disclosed and mockingly denounced the degraded debaucheries of the king and the king's friends. Subsequently he set up as a quack doctor under the name of Alexander Bendo, taking lodgings in Tower Street, and having a stall on Tower Hill. He amused himself by dispensing advice and cosmetics among credulous women. A speech which he is said to have delivered in the character of a medical mountebank proves him to have acted his part with much humour and somewhat less freedom than might have been anticipated (prefixed to the ‘Poetical Works of Sir Charles Sedley,’ 1710; Gramont, Memoirs). At another time, according to Saint-Évremond, he and the Duke of Buckingham took an inn on the Newmarket road, and, while pretending to act as tavern-keepers, conspired to corrupt all the respectable women of the neighbourhood. On relinquishing the adventure they joined the king at Newmarket, and were welcomed with delight.
With the many ladies of doubtful reputation who thronged the court Rochester had numerous intrigues, but he showed their waiting women as much attention as themselves. Elizabeth Barry [q.v.] , ‘woman to the Lady Shelton of Norfolk,’ he took into his keeping. He taught her to act, and introduced her to the stage, where she pursued a highly successful career. Some of his letters to her were published after his death. A daughter by her lived to the age of thirteen.
Despite his libertine exploits, Rochester succeeded in repairing his decaying fortune by a wealthy marriage. The king encouraged him to pay addresses to Elizabeth, daughter of John Malet of Enmere, Somerset, by Elizabeth, daughter of Francis, baron Hawley of Donamore. Pepys described her as ‘the great beauty and fortune of the north.’ Gramont called her a ‘melancholy heiress.’ Not unnaturally she rejected Rochester's suit, whereupon he resorted to violence. On 26 May 1665 the lady supped with the king's mistress, Frances Teresa Stuart (or Stewart) [q. v.], and left with her grandfather, Lord Hawley. At Charing Cross Rochester and his agents stopped the horses and forcibly removed her to another coach, which was rapidly driven out of London. A hue and cry was raised, Rochester was followed to Uxbridge, where he was arrested, and, on being brought to London, was committed to the Tower by order of the king (Pepys, Diary, ed. Wheatley, iv. 419). Miss Malet was not captured, and Rochester was soon released with a pardon. In 1667 he married the lady, and remained on fairly good terms with her till his death (cf. his letters to her in Whartoniana, 1727, vol. ii.).
Rochester's marriage did not alter his relations with the king or the court. In 1666 he was made a gentleman of the king's bedchamber. On 5 Oct. 1667, although still under age, he was summoned to the House
