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In 1976, Wincott starred in his first film, titled Earthbound, as Cole Buckley, a troubled teenager living in a small Saskatchewan town. Actors Kate Reid and Gerard Parkes played his parents in the film. The film aired on CBC-TV's Front Row Centre series in January 1977.
In 1979 Wincott starred in the Canadian adventure drama film Wild Horse Hank alongside Linda Blair. In 1981 he appeared in the Canadian drama film Circle of Two starring Richard Burton. He also appeared on two episodes of the Canadian TV Series The Littlest Hobo in 1979 and 1981.
After graduating from Juilliard, Wincott was cast in the 1987 film The Sicilian in the role of Corporal Silvestro Canio. That same year he was also cast in the Eric Bogosian play Talk Radio as a stoned heavy metal fan named Kent. The following year Wincott appeared in Oliver Stone's film based on the play. In the 1980s he also appeared on such American TV series as Miami Vice, Crime Story and The Equalizer, as well as Canadian police drama series Night Heat—a series starring his brother Jeff.
Wincott's stage performances include the off-Broadway productions Road (1988) starring Joan Cusack and Kevin Bacon, and the Sam Shepard play States of Shock (1991) starring John Malkovich. He also appeared on Broadway starring in the play Serious Money (1988) alongside Kate Nelligan, Alec Baldwin and John Pankow, as well as appearing in The Secret Rapture (1989) starring Blair Brown.
Wincott again worked with Oliver Stone in 1989, appearing in the film Born on the Fourth of July as a bedridden Vietnam veteran, then yet again in 1991 in the film The Doors where he played the role of Paul Rothchild, the producer of The Doors' first five albums. In 1991 he also played the part of Guy of Gisborne in Robin Hood: Prince of Thieves, a henchman of the Sheriff of Nottingham (Alan Rickman) who is also the Sheriff's cousin in the film.
In 1993 he appeared in the film Romeo Is Bleeding as Sal, a mafioso, and also played the part of Rochefort in the Disney film The Three Musketeers starring Kiefer Sutherland, Charlie Sheen and Chris O'Donnell. The following year Wincott starred as kingpin Top Dollar opposite Brandon Lee in The Crow. In 1995 he appeared in Dead Man with Johnny Depp. He played poet Rene Ricard in the 1996 biographical film Basquiat. He also played the role of mercenary Frank Elgyn in the 1997 film Alien Resurrection.
Wincott starred as a psychopathic kidnapper opposite Morgan Freeman in the 2001 film Along Came a Spider. The following year he played Armand Dorleac, a sadistic prison warden in the 2002 film version of The Count of Monte Cristo starring Jim Caviezel. In 2004 he played Julius Bicke, the brother of Samuel J. Bicke (played by Sean Penn) in The Assassination of Richard Nixon. In 2006 Wincott appeared in the western film Seraphim Falls starring Pierce Brosnan and Liam Neeson. He also appeared in The Diving Bell and the Butterfly and What Just Happened in 2007 and 2008 respectively.
In 2009 he starred in A Lonely Place for Dying as CIA project manager Anthony Greenglass. In early 2012 he was cast as notorious serial killer Ed Gein in the biographical drama film Hitchcock.
In 2014 Wincott played hacker Adrian Cross in the miniseries 24: Live Another Day. The following year he starred in the Canadian western drama film Forsaken alongside Kiefer and Donald Sutherland. In 2016 he also played the role of Old Bill in two episodes in season 1 of the science fiction western TV series Westworld.
In 2017 he appeared in the MTG drama series Veni Vidi Vici. The Swedish series stars Danish actor Thomas Bo Larsen and centers around the porn industry. Wincott plays the part of Georgina, a transgender former porn director. The show was selected as one of the top new European series at the MIPDrama Screenings held annually in Cannes. The series was also streamed on Hulu in 2017. Wincott starred in Jordan Peele's 2022 thriller, Nope, as Antlers Holst, a renowned cinematographer. In preparation for the role, Wincott shadowed the film's director of photography, Hoyte van Hoytema.
Wincott has also lent his voice to several characters in video games and animated features: In 2002 he provided the voice of Scroop, a malevolent spider/crab-like creature in the Disney animated film Treasure Planet; he also provided the voice of Scroop in the accompanying Sony PlayStation video game of the same name. In 2004 he provided the voice for the Prophet of Truth in the video game Halo 2. He also provided the voice of Mr. Big in the 2005 re-launch of the video game Narc. In 2012 he provided the voices for several video game characters: Jules Merit in the game Syndicate, Griffin in the interactive graphic novel Infex, and Death in the game Darksiders II.
Jordan Peele's "Nope" is almost here. Written and directed by the filmmaker, the movie was first announced in 2020. The cast includes Daniel Kaluuya, Keke Palmer, Steven Yeun, Barbie Ferreira, and Brandon Perea. Peele previously worked with Kaluuya for his directorial debut, "Get Out," making this a full-circle moment for the duo.
In the new trailer released on June 9, eager fans finally got a look at some plot details. Kaluuya and Palmer play siblings whose father dies while out on a horse on their family ranch, where they train horses for Hollywood movies. They believe his death is connected to a strange cloud in the sky, a UFO, and they decide to try to capture and sell the first real footage of UFOs — but it seems things quickly get out of hand.