At welterweight, he was London schoolboy champion on three occasions, fighting twice for England. Over the next 10 years, he won 80 out of 88 bouts. At the age of 12, Winstone joined the Repton Amateur Boxing Club. Known to his friends as Winnie, he was called Little Sugs at home (his father already being known as Sugar, after Sugar Ray Robinson). After borrowing extra tuition money from a friend's mother, a drama teacher, Winstone took to the stage, appearing as a Cockney newspaper seller in a production of Emil and the Detectives. Later, he viewed Albert Finney in Saturday Night and Sunday Morning, and said: "I thought, 'I could be that geezer'." Other major influences included John Wayne, James Cagney, and Edward G. Winstone had an early affinity for acting his father would take him to the cinema every Wednesday afternoon.
The room fell silent, then Ronnie cracked up, so everyone knew it was safe to join in."
He had a new mac on, which had probably cost a few bob, and I absolutely covered it. Everyone was on their best behaviour, but then Ronnie picked me up, and by all accounts I pissed all over him. "I was still a baby the day Ronnie Kray came round to see Dad, but I've been told this story so many times I can see it unfolding in my mind. He recounted an early encounter with a notorious gangster:
He did not take to school, eventually leaving with a single CSE (Grade 2) in Drama. He joined Brimsdown Primary School and later he was educated at Edmonton County School which had changed from a grammar school to a comprehensive upon his arrival. Winstone has recounted how, as a child, he used to play with his friends on bomb sites (vacant lots with rubble from World War II bombs). Winstone (1933–2015), ran a fruit and vegetable business while his mother, Margaret (née Richardson 1932–1985) had a job emptying fruit machines. He moved to Enfield when he was seven and grew up on a council estate just off the A10 road. He first lived in Caister Park Road, Plaistow E13, and attended Portway infants and junior school. Winstone was born on 19 February 1957 in Hackney Hospital, London. He has appeared in a wide variety of feature films, including Nil by Mouth (1997), Sexy Beast (2000), Ripley's Game (2002), The Magic Roundabout (2005), Beowulf (2007), Indiana Jones and the Kingdom of the Crystal Skull (2008), 44 Inch Chest (2009), London Boulevard (2010), Hugo (2011), Snow White and the Huntsman (2012), Point Break (2015), Cats (2019) and Black Widow (2021). Winstone has been described as one of the UK's "seminal screen hard nuts", while The Guardian has said that he "plays troubled hard men with such conviction, it's easy to believe he's not acting", adding that he is "the East End's answer to George Clooney".
In the 1980s he rose to prominence starring as Will Scarlet in the successful television series Robin of Sherwood.
The same year he played ex- army soldier Kevin in the cult classic Quadrophenia. The first of these was the character Carlin in Scum, the 1979 film remake of a BBC television play in which Winstone had originated the role, and which was not broadcast due to its violent nature. Having worked with many prominent directors, including Martin Scorsese and Steven Spielberg, Winstone is perhaps best known for his "hard man" roles (usually delivered in his distinctive London accent). Raymond Andrew Winstone ( / ˈ w ɪ n s t ən/ born 19 February 1957) is an English television, stage and film actor with a career spanning five decades.