Margaret was widowed while Edward was still a child. She then married an actor named Brown whose influence on his young stepson was to have a lasting effect upon the Elizabethan and Jacobean theatre, and in time upon the manor of Dulwich. It can be assumed that Edward played female roles during his boyhood, as was the custom. In 1584 when Alleyn was fourteen years of age, his name was recorded in the list of the Earl of Worcester's Players.
Bankside in Southwark was fast becoming a gathering ground for the entertainments of the City of London, which was only a short walk across London Bridge. It was here that Edward Alleyn met Philip Henslowe, a shrewd businessman and entrepreneur who had great financial interests in theatres, side-shows and the like. Alleyn soon became a business partner of Henslowe and on 22 October 1592, he married Henslowe's step-daughter, Joan Woodwarde. The newly married couple took up residence on Bankside in the Liberty of the Clink, within the Parish of St Saviour.
At the end of the sixteenth century Edward Alleyn was acclaimed as the leading actor of the time. He led, with Henslowe, the company of players known as My Lord Admiral's Men, later to become The Prince's Men in the reign of James l and Vl. He took the leading roles in the four great plays of Christopher Marlowe, Edward ll, Tamburlaine, the Jew of Malta and Dr Faustus. All of these were written before Marlowe's thirtieth birthday. It is believed that while at Cambridge, Marlowe had been recruited for government, probably as a spy. This activity was later to lead to the playwright's early demise in May 1593 when he was stabbed to death in a tavern brawl at Deptford.
In 1594 Alleyn bought an interest in the Bear Gardens for two hundred pounds and two years later Henslowe acquired part of the lease of another property. At this time Alleyn and Henslowe jointly held the office of Deputy Master of the Royal Game of Bulls and Bears. Having consolidated their position they started to develop their properties. In 1606 they contracted with a local carpenter, for £65, to pull down and rebuild the Bear Gardens.
The Bear Pit flourished and the Rose Theatre they also jointly owned was also extremely successful. Alongside these Alleyn and Henslowe ventures on Bankside were those of My Lord Chamberlain's Men headed by William Shakespeare and James Burbage. With a performance of Hamlet in January 1601, William Shakespeare opened the Globe Theatre on Bankside, built by Burbage who had dismantled and brought across the Thames the original timbers of 'The Theatre' in Shoreditch. Not to be outdone, Alleyn built the Fortune Theatre in the Parish of St Giles, Cripplegate and opened it in May of the same year. The new theatre was "like the late erected Plaiehose on the Banck in the said parish of the Ste Saviour called the Globe". Although Alleyn retired from acting in the following year, he remained manager of the Fortune Theatre until it was destroyed by fire on 9 December 1621.
Bear Baiting was a substantial source of income to Alleyn who, in 1604, was appointed by the King to be his 'Chief Master, Ruler and Overseer of all and singular of his majestie's games, of bears, and bulls, and mastive dogs, and mastive bitches'. This authorised him to take any bulls, bears or dogs from any part of the kingdom for the service of the king on payment of a 'fairprice'. Dogs were taken by Alleyn from the Bear Garden to the Tower of London in order to bait a lion in his den. In the early seventeenth century the Court gained much pleasure from animal baiting and this must have necessitated a great deal of forward planning for the 'Chief Master'. His acting talents, however, were not completely lost after his retirement from the stage, as Alleyn delivered congratulatory addresses on special occasions such as the City Pageant which was staged in March 1603 in honour of the Sovereign's visit.