For five or six years Cherry, familiarly known as 'Little Cherry,' enjoyed a high reputation in Dublin. His first part in the Smock Alley Theatre was Darby in the "Poor Soldier" of O'Keefe. 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. He first appeared as a member of Wilkinson's troupe at Wakefield as Vapid in the "Dramatist", and Lamrillo in Jephson's "Two Strings to your Bow". In the spring of 1794, Cherry, irritated that Fawcett, then on a starring tour, resumed his old parts, threw up his engagement with Tale Wilkinson and returned to Dublin, where he continued for two seasons, after which, with his wife, he engaged with Ward and Banks at the Theatre Royal, Manchester. Thence, to replace Blisset, he proceeded to Bath, in which city he made his first appearance on 6 October 1798.