Some of his best-known roles include Guy of Gisborne 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).
Wincott was born in Toronto and grew up in an east end suburb. His father is English while his mother was from Piacenza, Italy. Wincott also has two brothers, one of whom is actor and martial artist Jeff Wincott, a star of the late 80s TV series Night Heat.
In a 2014 interview with L'Uomo Vogue (the Italian edition of Men's Vogue) Wincott said he fell in love with cinema as a young child and took drama classes in High School. He was educated at the Victoria University, a college of the University of Toronto then in 1982 he enrolled at the Juilliard School in New York City, graduating in 1986. Wincott credited director Des McAnuff, as well as his father, with encouraging him to enroll at the prestigious acting school.

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