- Joined the Repton Amateur Boxing Club in London at age 12, winning 80 out of 88 fights over 10 years.
- Three-time London Schoolboy Champion.
- Represented England twice as a welterweight.
- Went to the movies weekly with his father; often they would sit through the films twice.
- Enrolled at the Corona Stage Academy in 1974, but was expelled for puncturing the headmistress' tires as revenge for being excluded from the Christmas party.
- First big role came when he accompanied a friend to an audition---and then was cast by the director---for the 1977 British TV-movie Scum, which was so violent that it was banned by the BBC; it was released theatrically two years later.
- Starred as a boxer named Kenny Fox in the 1980 British series Fox.
- During an audition for the first Star Wars prequel, asked an unimpressed George Lucas if he needed a nap (Winstone did not get the part).
- After twice being declared bankrupt, revived his career with a role in Kathy Burke's 1990 play, Mr. Thomas, which eventually led to a part in Gary Oldman's 1997 directorial debut, Nil by Mouth.
- During his audition for 2006's The Departed, director Martin Scorsese complimented him on his brown leather jacket and asked if he would wear it during filming. When Winstone said yes, Scorsese told him he got the part.
- 2007, Critics' Choice Awards — Best Acting Ensemble: Nominee
- 1998, BAFTA Film Awards — Best Actor in a Leading Role: Nominee
- 1980, BAFTA Film Awards — Most Promising Newcomer to Leading Film Roles: Nominee
- 2005, Australian Film Institute Awards — Best Lead Actor: Nominee
- 2001, European Film Awards — European Actor: Nominee
- 2006, Screen Actors Guild Awards — Outstanding Performance by a Cast in a Motion Picture: Nominee
- Raymond John Winstone — Father
- Lois Winstone — Daughter
- Ellie Rae Winstone — Daughter
- Margaret Richardson Winstone — Mother
- Jaime Winstone — Daughter
- Elaine McCausland Winstone — Wife
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