Charles Massey turns up initially in Philip Henslowe's diary as a player and later as a dramatist. He is listed ("Charles") with other members of the Admiral's men on 14 December 1594 as witnesses to the loan of £6 to "mr John" (Fol. 3). He continues to appear in the company "records as a borrower, as a witness, and as a representative of the company in its reckonings with Henslowe" (Nungezer, p. 147). He appears as a dramatist in conjunction with "Malcolm, King of Scots" in 1602, for which a suit of motley was purchased; and with "Siege of Dunkirk, with Alleyn the Pirate" in 1603. No other dramatist is associated with either play.
Evidence of his casting appears in the plot (1597) of "Frederick and Basilea", in which he played the role of Tamar.
Mark Eccles documents some aspects of Massey's personal life. He married a widow, Clemence Cowdall, at St. Benet, Paul's Wharf, on 9 May 1596. A widower by 1605, he married Elinor Colman at St. Gregory by St. Paul's. The couple had several children including Jane, baptised at St. Giles, Cripplegate, in 1610 (p. 298).
Massey had several encounters with the court system, making bail for his fellow player, John Singer, in 1614 in a case about stolen goods; and he was aided by George Massey in a suit by a pair of merchant taylors for debt. Some of the testimony in that suit says that Massey had recently been in debtor's prison (pp. 298-9). In 1613 Massey wrote to Edward Alleyn, requesting £50; in his plea for relief, he not only describes his own current financial peril but cites a pattern in which the company offered relief to players' widows Greg, Papers, MS. I, 67, p. 64).
Massey was one of several players who died during the plague of 1625.