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Leonard's career in film started with Hammer Film Productions, as he often styled Michael Carreras and other members of the Carreras family's hair. His first film with director Stanley Kubrick was in 1968 with "". For "A Clockwork Orange", Kubrick wanted actual hair cuts rather than wigs and "forerunners to the punk Mohawk hairstyle, with the sides of the head shaved and the middle part spiked up and brightly coloured." Leonard worked on "Barry Lyndon" and then followed with "The Shining". "Barry Lyndon" was highly stylised and required hundreds of intricate wigs. Starring Marisa Berenson and Ryan O'Neal, rumours circulated that each wig had its own first-class seat on the plane from London to Dublin. He also worked on Kubrick's film Full Metal Jacket.