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Monkhouse was born on 1 June 1928 at 168 Bromley Road, Beckenham, Kent, the son of Wilfred Adrian Monkhouse (1894–1957) and Dorothy Muriel Monkhouse née Hansard (1895–1971). Monkhouse had an elder brother, John, who was born in 1922. Monkhouse's grandfather John Monkhouse (1862–1938) was a prosperous Methodist businessman who co-founded Monk and Glass, which made custard powder and jelly. In a 2015 documentary, it was revealed that Monkhouse and his older brother suffered from physical and verbal abuse by their mother.
Bob Monkhouse was educated at Goring Hall School in Worthing, Sussex, and Dulwich College in south London, from which he was expelled for climbing the clock tower.[ While still at school, Monkhouse wrote for The Beano and The Dandy and drew for other comics including Hotspur, Wizard and Adventure. He established a comics writing and art partnership with Dulwich schoolmate Denis Gifford and the two formed their own publishing company in the early 1950s. Among other writing, Monkhouse wrote more than 100 Harlem Hotspots erotic novelettes.[5]
Monkhouse completed his National Service with the Royal Air Force in 1948. He won a contract with the BBC after his unwitting RAF group captain signed a letter that Monkhouse had written telling the BBC he was a war hero and that the corporation should give him an audition.
Before establishing himself as a successful writer and comedian, Monkhouse appeared on stage in London, first as Aladdin in a stage show of the same name written by S. J. Perelman and Cole Porter and then in the first London production of the musical The Boys from Syracuse (Antipholus of Syracuse) in 1963 at the Theatre Royal, Drury Lane, alongside Ronnie Corbett.
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