At eleven years of age, however, Cherry left the Limerick from school and entered the employment of James Potts, a printer and bookseller in Dublin.

[1] 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.

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.

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.

Early in the season of 1791–2, he appeared with his wife in Hull as a member of the company of Tate Wilkinson, playing comic characters previously assigned to Fawcett, who had just quit the York circuit for Covent Garden.

[1] From Bath, he made his way to Drury Lane, at which house he appeared for the first time on 25 September 1802 as Sir Benjamin Dove in the Brothers of Cumberland, and Lazarillo in Two Strings to your Bow.