[3] Dibdin's mother was initially against her son following a theatrical career and so arranged for him to start an apprenticeship for his uncle Cecil Pitt, a furniture-maker, who worked in central London.
Keen to realize a literary ambition, Dibdin published a collection of verse, Poetical Attempts: by a Young Man in 1792[3] and along with his brother Thomas, wrote the Christmas pantomime The Talisman; or, Harlequin Made Happy in 1796.
[5] In 1797 he recommenced his performing career at the Royalty Theatre in London in a one-man show called Sans six sous and became known professionally as Charles Dibdin the younger.
[6] In 1799, Dibdin was offered a contract by the Sadler's Wells manager Richard Hughes to write pantomimes and harlequinades for the following year's season,[10] including Harlequin Benedick; or, The Ghost of Mother Shipton and The Great Devil, both starring Joseph Grimaldi.
[3] In 1800, Dibdin took over as manager at Sadler's Wells Theatre in London with the pantomime ballet Filial Love, or the Double Marriage being one of the first pieces to be staged under his managership.
These spectacles improved the fortunes of Sadler's Wells, and by 1802 he, his brother Thomas and a syndicate of wealthy businessmen, including the scene painter Robert Andrews and composer William Reeve, became shareholders in the theatre.
Although his proprietorship survived the disaster, the Napoleonic wars of 1803-1815 had ruined public demand for Dibdin's type of entertainment, and his fortunes fell until, in 1819, he was declared bankrupt and was incarcerated in a debtors' prison.
[17] The author Andrew McConnell Stott noted "[Dibdin] was a cheerful, tireless and frequently prosperous man with a love of patriotic ballads and convivial dinners.