Winstone was born in Homerton, in the London Borough of Hackney. His family was originally from Cirencester, Gloucestershire – half of them moving to London, the other half to Wales. Moving via Plaistow to Enfield when Winstone was seven, his father, Raymond Andrew Winstone, Sr., ran a fruit and vegetable business (he is now a black cab driver) while his mother, Margaret, had a job emptying fruit machines.

Winstone recalls playing with his friends on bomb sites until "Moors Murderers" Ian Brady and Myra Hindley were arrested after preying on children. Winstone was educated at Edmonton County, which had changed from a grammar school to a comprehensive upon his arrival. He didn't take to school, eventually leaving with a single CSE (Grade 2) in Drama.

After a short run in the TV series Fox, and a role in Ladies and Gentlemen, The Fabulous Stains (alongside Diane Lane, Laura Dern and a host of real-life punks like Fee Waybill, Steve Jones, Paul Cook and Paul Simonon), Winstone got another big break, being cast as Will Scarlet in Robin of Sherwood.

He proved immensely popular and enjoyed the role, considering Scarlet to be "the first football hooligan" - though he was not fond of the dubbed German version, in which he said he sounded like a "psychotic mincer." But once the show was over, the parts dried up. He got involved in co-producing Tank Malling, starring Jason Connery, Amanda Donohoe and Maria Whittaker, and scored a few TV parts.

Over the years, he's appeared in TV shows including The Sweeney, The Bill, Boon, Fairly Secret Army (as Stubby Collins), Ever Decreasing Circles, One Foot in the Grave, Murder Most Horrid, Birds of a Feather, Minder, Kavanagh QC, Auf Wiedersehen, Pet and Get Back (with the fledgling Kate Winslet.) During this period, he was increasingly drawn to the theatre, playing in Hinkemann in 1988, Some Voices in 1994 and Dealer's Choice and Pale Horse the following year.

Winstone was asked to appear in Mr Thomas, a play written by his friend and fellow-Londoner Kathy Burke. The reviews were good, and led to Winstone being cast, alongside Burke, in Gary Oldman's drama Nil By Mouth. As an alcoholic wife-batterer, he was lauded across the board, receiving a BAFTA nomination (17 years after his Best Newcomer award for That Summer).

He continued to play tough guy roles in the likes of Face and The War Zone — the latter especially controversial, as he played a father who rapes his teenage daughter — but that obvious toughness would also allow him to play decent men softened by love in romantic comedies like Fanny and Elvis and There's Only One Jimmy Grimble.

In Last Christmas, he played a dead father, now a trainee angel, who returns from Heaven to help his young son cope with his bereavement, written by Tony Grounds who Ray worked with again on Births, Marriages & Deaths and Our Boy winning Ray the Royal Television Society Best Actor Award. They worked together again in 2006 on All in the Game where Ray gives a virtuoso performance as a football manager. He did a series of Holsten Pils ads where he played upon the phrase "Who's the Daddy", coined in the film Scum.

In 2000 Winstone starred along side Jude Law in the hit cult film Love, Honour and Obey, then snagged a role as Gary 'Gal' Dove in Sexy Beast, that brought him great acclaim from UK and international audiences, and brought him to the attention of the American film industry.

Winstone plays a retired and happily married former thief, living off of his spoils in Spain, dragged back into London's underworld by two psychopathic former associates (played by Ian McShane and Ben Kingsley, who received an Oscar nomination for his performance).

After a brief role alongside Burke again in the tragi-comic The Martins, he appeared in Last Orders, directed by Fred Schepisi (of Roxanne fame), where he starred alongside the weighty likes of Michael Caine, Helen Mirren, David Hemmings and Tom Courtenay. Before shooting began, he was fearful that meeting these actor-heroes (he loved the likes of Zulu and The Loneliness of the Long Distance Runner) might turn out to be disappointing. He later said his co-stars were as impressive as he'd hoped, however.

Next Winstone would nab a prime part in Ripley's Game, the sequel to The Talented Mr. Ripley, in which he once again played a cold-bloodedly violent gangster. He followed up with Lenny Blue, the sequel to Tough Love, and the short The Bouncer.

In 2000, he starred in To the Green Fields Beyond at the Donmar Warehouse (directed by Sam Mendes, the man behind American Beauty). 2002 would see him at the Royal Court, as Griffin in The Night Heron. Two years later, he joined Kevin Spacey for 24 Hour Plays at the Old Vic, a series of productions that were written, rehearsed and performed in a single day. Now internationally known, Winstone was next chosen by Anthony Minghella to play Teague, a sinister Home Guard boss, in the Civil War drama Cold Mountain.

Perhaps inspired by Burke and Oldman, Winstone has now decided to direct and produce his own movies, setting up Size 9 and Flicks production companies with his long-time agent Michael Wiggs. The first effort was She's Gone, in which he plays a businessman whose young daughter disappears in Istanbul (filming was held up by unrest in the Middle East.) He followed it up with Jerusalem in which he played poet and visionary William Blake.

Winstone made his action movie debut in King Arthur, starring Clive Owen, directed by Antoine Fuqua, and produced by Jerry Bruckheimer. In that film, Fuqua proclaimed him as "the British De Niro." He then provided the voice of Soldier Sam in the long-awaited screen version of The Magic Roundabout.

In 2005, he appeared opposite Suranne Jones in ITV drama Vincent about a team of private detectives. He returned to the role in 2006 and was awarded an International Emmy. In 2005 he also portrayed a 19th century English policeman trying to tame the Australian outback in The Proposition. A complete change of pace for Winstone was providing the voice for the plucky Mr. Beaver in The Chronicles of Narnia: The Lion, the Witch and the Wardrobe, also in 2005.

Winstone appears in the 2006 crime thriller by Martin Scorsese, The Departed as Mr. French, an enforcer to Jack Nicholson's Boston Irish mob boss. He provided motion capture movements and voice for the Beowulf character in the Robert Zemeckis' film Beowulf. He starred in the fourth Indiana Jones film Indiana Jones and the Kingdom of the Crystal Skull, which was released on 22 May 2008.

He is set to play the role of Detective Inspector Jack Regan in a remake of The Sweeney, He is currently filming '44 Inch Chest' and plays the lead role along side John Hurt and Ian McShane as Colin Diamond a husband scorned by his love for his unfaithful wife. He has also been cast as CIA agent Darius Jedburgh in the Edge of Darkness remake, after Robert De Niro left the film.