He was nominated for the Independent Spirit Award for Best Supporting Male for his performance in the film Steel City.

Barry is known for his roles in the film Interview with the Assassin,[4] portraying Walter Ohlinger, a man who claimed to be the second shooter on the Grassy Knoll in the assassination of John F. Kennedy, and as Ron Kovic's father in the Academy Award-winning film Born on the Fourth of July.

[4] Other films in which he appeared include: Dead Man Walking,[4] Cool Runnings, K2,[4] The Tulse Luper Suitcases, Falling Down, and Training Day.

[4] On television, he has appeared as Jack Shephard's grandfather in Lost,[4] as Fox Mulder's congressional patron, Senator Richard Matheson, in The X-Files,[4] and as Lilly Rush's father in CBS series Cold Case.

[4] Barry appeared in two films focusing on the death penalty, Dead Man Walking and The Chamber, both with actor Robert Prosky.