Dale's film debut was in Six Five Special (1958), a spin-off from the BBC TV series of the same name. This film was also released under the name 'Calling All Cats'. He then had a tiny role as a trombone player who thwarts orchestral Conductor Kenneth Williams in the comedy Raising the Wind (1961). However, he is best known in Britain for his appearances in eleven Carry On films, a long-running series of comedy farces, generally playing the hapless romantic lead. His Carry On career began in small roles: first as an expectant father in Carry On Cabby (1963), and was followed by Carry On Jack (1963). From Carry On Spying (1964) onwards, his roles were more substantial. Following Carry On Cleo (1964), his first principal role was Carry On Cowboy (1965), set in the Wild West, where he played an immigrant English sanitary Engineer called Marshall P. Knutt who is mistakenly hired as a police marshal. Then came Carry On Screaming! (1966), Don't Lose Your Head (1966), Follow That Camel (1967), Carry On Doctor (1967), Carry On Again Doctor (1969) and the 1992 revival Carry On Columbus.