- Was offered the role of Jimmy McNulty in The Wire (2002), which he turned down because he didn't want to move to Baltimore, away from his family. The role instead went to Dominic West.
- Has three children: Lois Winstone (born 1982), a singer with the London-based hip-hop group "Crack Village" who also played his on-screen daughter in Last Orders (2001) and got a part in four episodes of The Bill (1984), Jaime Winstone (born 1985) also an actress with ambitions to be a director, and Ellie Rae Winstone (born 2001).
- Was the leading actor in the directorial debuts of two Brit actors: in The War Zone (1999) directed by Tim Roth and in Nil by Mouth (1997), directed by Gary Oldman. All three are known for playing villains in many films.
- Supports West Ham United Football Club
- Starred in the short lived TV series Ghostbusters of East Finchley (1995). Although this series was completely unrelated to Ghostbusters (1984), the original Ghostbusters had characters named Ray and Winston.
- As a boxer he won 80 out of 88 fights,.
- Ray Winstone did extra work for one day on the Michael Apted film Stardust (1974). He can be glimpsed wearing a white jacket around the 6:27, 6:36, and 8:04 minute marks.
- Son of a greengrocer.
- His interest in the cinema came about through his greengrocer father taking him to the cinema every week.
- Is currently learning to ride a horse.
- One of 105 people invited to join AMPAS in 2008.
- Trained at the Corona Academy, founded by Rona Knight.
- Will be conducting an Acting Masterclass at the Cinemagic World screen Festival for Young People 2002, in Belfast N.Ireland.
- In 2001 he co-founded production company Size 9 Productions with Joshua St Johnston and Michael Wiggs.
- The Robin of Sherwood International fanclub can be reached by sending a SASE or IRC to Spirit of Sherwood, 1276 W. Marshall, Ferndale, Michigan 48220, USA or email ChrisRHood@aol.com
- In the Isle of Man, filming Darkness Falls (1999) ("Dangerous Obsessions"). (September 1997)
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