Was the original voice of Tack the Cobbler, the hero of Richard Williams's animated cult masterpiece The Princess and the Cobbler (1993). In the original version (from the work print and the resulting "Recobbled" fan-restoration), Tack was mute until the very end, when he spoke in Sean Connery's voice.
Wears a toupee in all the James Bond movies. He started losing his hair at the age of 21. Privately and in most other movies, he wears none.
Whilst filming Playing by Heart (1998) he loved playing and even made a friendship with three and a half year old Piper Maru Anderson; daughter of an actress Gillian Anderson who played Meredith (a daughter of Sean's character).
With the death of Kieron Moore on July 15, 2007, he is the last surviving cast member of Darby O'Gill and the Little People (1959).
Won the role of James Bond after producer Albert R. Broccoli attended a screening of Sean in Darby O'Gill and the Little People (1959). He was particularly impressed with the fistfight Sean has with a village bully at the climax of the film. Cubby later had his wife, writer Dana Broccoli, see the film and she confirmed his sex appeal.