[3][4][6][7][8][9] Some of his best-known roles include Guy of Gisbourne in Robin Hood: Prince of Thieves (1991); Top Dollar, the main antagonist in The Crow (1994); music mogul Philo Gant in Strange Days (1995); mercenary Frank Elgyn in Alien Resurrection (1997); hacker Adrian Cross on the TV miniseries 24: Live Another Day (2014); and cinematographer Antlers Holst in Nope (2022).
[3][5][6][10][11] He has frequently worked with directors Oliver Stone and Julian Schnabel, and appeared in films by Ridley Scott, Terrence Malick, Michael Cimino and Jim Jarmusch.
[1][15] Wincott credited director Des McAnuff, as well as his father, with encouraging him to enroll at the prestigious acting school.
[15] In 1976, Wincott starred in his first film, titled Earthbound, as Cole Buckley, a troubled teenager living in a small Saskatchewan town.
[16][17][18] In 1979, Wincott starred in the Canadian adventure drama film Wild Horse Hank alongside Linda Blair.
[15] That same year he was also cast in the Eric Bogosian play Talk Radio as a stoned heavy metal fan named Kent.
[6][8] 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.
[26] In 2006, Wincott appeared in the western film Seraphim Falls starring Pierce Brosnan and Liam Neeson.
[29] The following year he starred in the Canadian western drama film Forsaken alongside Kiefer and Donald Sutherland.
[30] In 2016 he also played the role of Old Bill in two episodes in season 1 of the science fiction western TV series Westworld.