In addition to working at various theaters, Chetwood was a bookseller, novelist, and playwright. His many plays, however, were not very lucrative or acclaimed; his prose fiction was more successful. Throughout the '30s, he declined in prosperity, and the first of a series of dire financial problems arose in 1741, when he became imprisoned in the King's Bench and a performance of William Congreve's The Old Bachelor was advertised as for his benefit. His collection Five New Novels, a piece of hack writing, probably helped secure his release. When in debtor's prison again in Dublin in the 1750s, he wrote poetry and published editions of plays by Henry Shirley (1750) and Ben Jonson (1756) in the hopes of amending his financial difficulties. He was arrested for debt yet again in 1760, prompting another theatrical benefit. He eventually died in prison. The DNB characterizes him as "an active but minor participant in the theatrical and publishing worlds of the first half of the 18th c."