From an early period, he displayed a taste for the stage, and at the age of fourteen he played as an amateur, in a room at the Black-a-Moor's Head, Towers Street, Dublin, Lucia in Addison's "Cato". Three years later be first appeared at Naas, county Kildare, as a member of a strolling company under the management of a Mr. Martin, playing Feignwell in "A Bold Stroke for s Wife". As a strolling player in Ireland, he purchased, at the cost of constant exposure and imminent risk of starvation, a fair knowledge of his art. According to the accounts of his career published during his lifetime, he was on one occasion three days without food. Yielding to discouragement he returned to his former occupation and remained in Dublin for three years. After one or two attempts to resume his profession of an actor he joined the company of Richard William Knipe, a well-known and popular manager, whose daughter, after the death of her father, he married in Belfast. Cherry then joined the 'principal provincial company of Ireland' under the management of Atkins, and played with an increasing reputation in the north of Ireland a round of leading characters. Mr. Ryder having in 1787 been engaged for Covent Garden, Mr. Cherry was called up to supply his place at the Theatre Royal, Smock Alley, Dublin. As Ryder's first appearance took place on 25 October 1766, this data is seen to be not wholly trustworthy.