During the final decade of his life, in disenchantment with the state of England – so Anne Barton (1984) has suggested – Jonson turned nostalgically back to the England of Elizabeth, his taste for retrospection being evident in the themes and structure of such late plays as The New Inn, presented by the King's Men early in 1629, and A Tale of a Tub, performed by Queen Henrietta's Men at the Cockpit ‘as new’ in May 1633. Recent scholars, however, have detected in these plays a close engagement with social and political issues of the day, and with the ideology of the Caroline court (Butler, 1992c; Sanders, 1998a; Maxwell, 2002). The atmosphere of that court had been dramatically changed by the assassination of the unpopular royal favourite, George Villiers, Duke of Buckingham, on 23 August 1628. This event was one with which Jonson had been curiously entangled, having been interrogated on 26 October 1628 by the Attorney-General, Sir Robert Heath, concerning his possible authorship of verses commending the action of Buckingham's assassin, John Felton. The charge was denied by Jonson, and finally dismissed (Life Records, 76; Dubia, ‘Felton Commended’).

Despite its remarkable virtuosity, The New Inn did not succeed in the theatre. The title-page of the octavo edition of the play, published in 1631, laid the blame on the company, caustically declaring that the comedy ‘was never acted, but most negligently played, by some, the King's Servants, 1629’. In the scornful ‘Ode to Himself’ Jonson vowed to ‘leave the loathèd stage’ and to direct his remaining energies to praising the present king, ‘tuning forth the acts of his sweet reign’ (59). Jonson's quarrel evidently lay chiefly with the theatre, not with his monarch.

An engraving of Jonson made in or around 1627 by Robert Vaughan (see Frontispiece, volume 6, possibly based on a portrait by the Dutch artist Abraham van Blyenberch, a version of which hangs in the National Portrait Gallery, London) shows a scraggily bearded, heavily built figure, with ‘one eye lower, than tother, and bigger’ (as Aubrey was later to describe him; Electronic Edition, Early Lives). He is plainly dressed and crowned with laurel, and stares gloomily through an oval border whose inscription proclaims him doctissimi poetarum anglorum, the most learned of English poets. The melancholic look may perhaps reflect the sharp decline in Jonson's health that began in these years. Late in 1627 or early in 1628 he appears to have suffered a paralytic stroke. He was by now grossly overweight and further affected by a ‘palsy’ which, in Clarendon's words, ‘made a deep impression upon his body and his mind’ (Clarendon, 1759, 16). In a late poem he wryly views himself as ‘a tardy, cold, / Unprofitable chattel, fat and old, / Laden with belly’, who ‘doth hardly approach / His friends, but to break chairs, or crack a coach’ (Und. 56.7–10).

Poverty compounded these afflictions. On 19 January 1629 a grant of £5 was made by the Dean and Chapter of Westminster ‘to Mr Beniamin Jhonson in his sicknes and want’, and in March of the same year Jonson thanked King Charles in verse for ‘a Hundred Pounds He Sent Me in My Sickness’ (Und. 62). Jonson's poems and letters written during the last period of his life – especially those to his new and watchful patron, William Cavendish, Earl of Newcastle – return touchingly to these practical problems now besetting his life. "Disease, the enemy, and his engineers, / Want, with the rest of his concealed compeers, / Have cast a trench about me, now, five years", he wrote in 1631 in an ‘Epistle Mendicant’ addressed to the Lord High Treasurer, Lord Weston (Und. 71.4–6).