Winstone stayed visible following his big break with starring roles on British television and smaller parts in film, but for many years failed to capture the promise displayed by his debut work. He headlined the British series "Fox" (1980), played a recurring part as a gangster in "A Fairly Secret Army" (1984) and essayed Will Scarlett in the adventure "Robin of Sherwood" (1984-86). But Winstone has admitted to have taken some poorly conceived roles and turning in uninspired performances both on film and television during the 1980s. An impressive stint in "Mr. Thomas" (1990), a play written and directed by Kathy Burke and performed in London's fringe theater, proved the antidote to his rut, helping restore his confidence as well as garnering acclaim for his performance. In 1994, he had a supporting role in Ken Loach's emotionally raw "Ladybird, Ladybird", and would, with age and experience gravitate more towards complex roles, taking on characters with undeniable, often violent, faults, but portraying them with an intricate dimensionality, evincing from the audience sympathy as well as disgust and horror.

"Nil By Mouth" (1997) would jumpstart his career and fulfilled the promise of his earliest performances. Reuniting with Kathy Burke, Winstone this time played her violent and mercurial husband, a character despised but also embraced by viewers, largely due to his powerful and nuanced performance which combined affable charm with frightening brutality. Written and directed by Gary Oldman, marking that actor's feature debut in those capacities, the honest, well-crafted film was a moving and disturbing account of one working class family's life that justly won acclaim and prestige. Following the filming of "Nil By Mouth", but prior to its successful release, Winstone was featured in "Face" (1997), Antonia Bird's film chronicling a group of career criminals whose relationships become unraveled by a traitor in their midst. Co-starring as Dave, a seemingly levelheaded small-time grifter with big-time plans who lands in a desperate situation, he again was able to make a pathetic and brutal character likable. In "Our Boy" (also 1997), he played a father who is utterly destroyed following his young son's accidental death, offering a moving performance in this heartrending tale that aired on British television and screened at film festivals.

Other television projects of note include his take on the successful, slick and calculating Alan in "Births, Marriages and Deaths" (1999), a four-part BBC series following the goings on at a stag party which leads to the airing out of family secrets and scandals. Winstone continued to offer stirring performances in uncompromising roles, including his disturbing turn as a father who rapes his teenaged daughter in Tim Roth's "The War Zone" (1999), screened at both Sundance and Cannes Film Festivals. Attendees of the latter could also see him as a loan shark in 1967 Dublin in "Agnes Browne", directed by and starring Anjelica Huston. Additionally, he turned in a solid performance in the less prestigious thriller "Dangerous Obsession" (1999), playing a rampaging intruder who has personal stake in his captives, and displayed a lighter side in a supporting role in the romantic comedy "Martha, Meet Frank, Daniel and Lawrence" (1998, released in 1999 in the USA under the title "The Very Thought of You").

Having re-established himself as an actor of note with these films and subsequent roles in UK television and film productions, Winston's mid-career renaissance continued unabated, with notable roles as a London crime boss in the comedic crime noir "Love, Honour and Obey" (2000), as Gal Dove, the retired safecracker who refuses to answer ferocious Don Logan's (Ben Kingsley) increasingly threatening call to return to work in "Sexy Beast" (2001) and as Michael Caine's foster son in "Last Orders" (2001). In 2002 Winstone appeared in writer-director Liliana Cavani's "Ripley's Game," an unofficial sequel to "The Talented Mr. Ripley" (based on the novel by Ripley creator and author Patricia Highsmith) as an associate to the older, successful Tom Ripley (John Malkovich) who calls on his old friend for some homicidal help. The actor also had a plumb role in "Cold Mountain" (2003) playing the villainous Teague who plots to usurp the lands—and the hand of Nicole Kidman—of Cold Mountain's Confederate Army deserters.

In 2003, the actor starred as England’s most powerful and independent monarch in “Henry VIII” (PBS), a British-made miniseries that focused on the king’s reign and his six volatile marriages. Winstone proved to be an excellent choice for the role, not only because of his dynamic onscreen presence, but also for his striking resemblance to the famed monarch. Meanwhile, he returned to feature films with a supporting role in the more historically accurate but ultimately uneven actioner, “King Arthur” (2004), starring Clive Owen as a Roman Cavalryman torn between religious devotion to Rome and loyalty to his native Britannia. Winstone played Bors, one of Arthur’s determined but conflicted knights who helps try to unite a divided land amidst retreating Romans and invading Saxons. He next appeared in “The Proposition” (2005), a brutal western set in late-19th century Australia in which he portrayed a ruthless lawman who pits three notorious outlaw brothers against each other. Winstone was nominated for Best Actor at the 2005 Australian Film Industry Awards.

In another rare turn for the actor, Winstone provided the voice of Mr. Beaver, one of several all-CGI characters in “The Chronicles of Narnia: The Lion, the Witch and the Wardrobe” (2005), the relentlessly hyped big budget fantasy adventure based on the C.S. Lewis novel series. He also voiced a character in “Doogal” (2006), a British-made animated feature based on the classic cult French television series, “The Magic Roundabout” (BBC, 1965-1975). Winstone was next seen in “The Departed” (2006), director Martin Scorsese’s star-studded crime thriller about a cop (Leonardo DiCaprio) deep undercover inside a crime syndicate ran by Frank Costello (Jack Nicholson), a sexually deviant mob boss who has one of his own (Matt Damon) undercover on the police force. As both institutions do battle to bring the other side down, the two moles struggle to reveal each other without having their own cover blown. “The Departed” earned the blessing of most critics, many of whom called it Scorsese’s best film in years.

Meanwhile, Winstone had a supporting role in “Breaking & Entering” (2006), an ensemble drama about a young Muslim man who breaks into the office of a yuppie architect in London and sets off a series of related events that intersect the two men’s lives with the seedy inner-city area of Kings Cross. Then in “Beowulf” (2007), Winstone had the title role in the adaptation of the famed eighth century poem about a sixth century warrior who does battle with a monster named Grendel.