Rose, and that or other companies occupied it almost continuously till 1603, when a quarrel between Henslowe and the ground landlord led him to close his connection with the house. He threatened to demolish it at the time. Meanwhile, he managed the theatre at Newington Butts when the lord admiral's and lord chamberlain's companies were acting together there in 1594. Towards the close of the century he seems to have taken some part in the management of the Swan Theatre, which, like the Rose, was on the Bankside. On 15 Oct. 1592 his step-daughter, Joan Woodward, had married Edward Alleyn the actor [q. v.], and his relations with Alleyn in business and in private life were thenceforth very close. On 26 Sept. 1598 an interesting extant letter from him to Alleyn, who was then in the country, mentions the murder by Ben Jonson of Gabriel Spencer, a member of Alleyn's company. In 1600 he and Alleyn built a new theatre called the Fortune in Golden Lane, Cripplegate Without. It was square in shape, was the largest playhouse of the time, and was opened in November 1600. Until his death Henslowe actively interested himself in the affairs of the Fortune, which was subsequently burnt down (9 Dec. 1621).
Henslowe and Alleyn were also connected with less elevated entertainments. In December 1594 they secured a substantial interest in the Paris Garden, devoted to bear-baiting, on the Bankside. They failed in 1598 in a joint application for the mastership of the royal game of bears, bulls, and mastiff dogs, but purchased the office from the holder in 1604, and secured a patent in their favour on 24 Nov. in that year. Many bears and lions belonging to the crown were thenceforth entrusted to their care (Cal. State Papers, Dom. 20 March 1611). In February 1610–11 Alleyn sold to Henslowe his interest in the Bear Garden, and on 29 April 1613 Henslowe and a new partner, Jacob Meade, ‘waterman,’ arranged for the demolition of the existing buildings, and for the erection of a new building, to be called the Hope, fitted for stage-plays, as well as for bull- and bear-baiting exhibitions. A new inn called the Dancing Bears was erected at the same time in the Garden, and there Meade resided. He, rather than Henslowe, managed the new Hope playhouse.
During Henslowe's tenure of the Rose and Fortune theatres plays by many of the leading Elizabethan dramatists were first put on the stage, and he was in intimate relations with the authors. His extant account-book proves that he bought plays direct from the authors, and hired them out at a profit, together with the necessary properties, to various acting companies. Among those who sold their works to him were Dekker, Drayton, Chapman, Chettle, Day, and Rowley. The highest price paid by him for a play before 1600 was 6l.; after that date the price sometimes rose to 10l., but in many cases four, five, or even six authors were concerned in the composition, and shared in the emolument. The receipts, inserted in the extant diary, of moneys paid to dramatists by Henslowe are signed, and in some instances fully written out, by the recipients themselves, and thus some unique autographs are preserved. Henslowe often lent the authors small sums of money on account of promised work, and invariably kept them in humiliating subjection to himself. He always looked carefully after his security. Frances, wife of Robert Daborne [q. v.], one of his most needy clients, stated at the time of Henslowe's death that he had in his possession all Daborne's manuscripts, together with a bond for 20l. as security for some loan; these Henslowe restored a few hours before he died (Rendle).
Fully two-thirds of the plays mentioned by Henslowe as being acted under his management are now lost. Although plays by Marlowe, Chapman, and Dekker were repeatedly performed at his theatres, no play mentioned by him can be identified with any by Shakespeare. Shakespeare belonged to and wrote almost solely for the lord chamberlain's company of players, and that company only on one occasion came into contact with Henslowe or his theatres, namely, in 1594. The lord chamberlain's men then combined with the lord admiral's men, a company always more or less associated with Henslowe, to give some performances under Henslowe's management at the theatre in Newington Butts.
Henslowe died on 6 Jan. 1615–16, and was buried in the chancel of St. Saviour's Church, Southwark, on 10 Jan. 1615–16, ‘with an afternoon knell of the church bell.’ By his will, dated 5 Jan. 1615–16, he left all his lands and tenements to Agnes, his wife, whom he admits not to have used very well, although he derived much of his fortune from her. The overseers of his will were Edward Alleyn, Robert Bromfield, William Austin (1587–1634) [q. v.], and Roger Cole. The will was disputed by Henslowe's nephew, John Henslowe, but depositions made by witnesses in connection with the dispute agree that, although Henslowe was suffering from the palsy, his mind was quite clear to the last.
The volume containing Henslowe's diary and accounts, with many of his letters and other papers relating to him, is now preserved in Dulwich College library. The diary deals mainly with the expenses of his management
