He was known for his portrayal of a Louisiana sharecropper who struggles to support his family during the Great Depression in the landmark film Sounder (1972), which earned him an Academy Award nomination.

Winfield became well known to TV audiences when he appeared in several seasons of the groundbreaking television series Julia opposite Diahann Carroll.

The show, filmed during a high point of racial tension in the U.S., was unique in featuring a black female as the central character.

Winfield also appeared in a different role in the 2003 Disney-produced TV remake of Sounder directed by Kevin Hooks, his co-star from the original.

Winfield also starred in several miniseries, including Scarlett, and two based on the works of novelist Alex Haley: Roots: The Next Generations and Queen: The Story of an American Family.

Winfield gained a new segment of fans for his brief but memorable roles in several science fiction television series and films.

In 1996, he was in the 'name' ensemble cast in Tim Burton's comic homage to 1950s science fiction Mars Attacks!, playing the complacently self-satisfied Lt. General Casey.

On the small screen, he appeared in the Star Trek: The Next Generation episode "Darmok"[9] as Dathon, an alien captain who communicates in allegories.