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. 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. The following year Wincott appeared in Oliver Stone's film based on the play. That same year he was also cast in the Eric Bogosian play Talk Radio as a stoned heavy metal fan named Kent. Īfter graduating from Juilliard, Wincott was cast in the 1987 film The Sicilian in the role of Corporal Silvestro Canio. He also appeared on two episodes of the Canadian TV Series The Littlest Hobo in 19. In 1981 he appeared in the Canadian drama film Circle of Two starring Richard Burton.
In 1979 Wincott starred in the Canadian adventure drama film Wild Horse Hank alongside Linda Blair. The film aired on CBC-TV's Front Row Centre series in January 1977. Actors Kate Reid and Gerard Parkes played his parents in the film.
In 1976 Wincott starred in his first film, titled Earthbound, as Cole Buckley, a troubled teenager living in a small Saskatchewan town. Wincott credited director Des McAnuff, as well as his father, with encouraging him to enroll at the prestigious acting 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. 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. 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. His father is English while his mother was from Piacenza, Italy. Wincott was born in Toronto and grew up in an east-end suburb.
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