Chris Cooper made his debut in the 1987 American drama film ‘Matewan’ directed by John Sayles. Despite opening to critical acclaim, the film failed to achieve success at the box office. That same year, he also appeared in the Episode: "The Rehearsal" of the American spy thriller television series ‘The Equalizer.’ He continued to appear in television series such as ‘American Playhouse’ (1988), ‘Miami Vice’ (1998), ‘Lonesome Dove’ (1989), and ‘Lifestories’ (1990). In 1991, he starred as ‘Larry Nolan’ in the American drama film ‘Guilty by Suspicion’ directed by Irwin Winkler. The film garnered praise from critics. That same year, he also appeared in the American drama film ‘City of Hope’ which also received positive reviews from critics. He next starred in films like ‘This Boy's Life’ (1993), ‘Pharaoh's Army’ (1995), ‘Money Train’ (1995), ‘Boys’ (1996), ‘Lone Star’ (1996), ‘Breast Men’ (1997), and ‘Great Expectations’ (1998).
The year 1999 saw the release of the American black comedy-drama film ‘American Beauty’ where Cooper played the role of ‘Col. Frank Fitts.’ The film saw universal acclaim upon release and was a massive box office success, grossing over $356.3 million on a budget of $15 million. Cooper also received the ‘Screen Actors Guild Award’ nomination for his performance in the film. The following year, he starred as ‘Lt. Gerke’ in the American black comedy film ‘Me, Myself & Irene’ directed by Peter Farrelly and Bobby Farrelly. The film opened to a mixed reception and was a commercial success. In 2002, he portrayed ‘John Laroche’ in the American meta comedy-drama film ‘Adaptation’ directed by Spike Jonze. The film opened to wide critical acclaim and was ranked amongst the thirty best films of the 2000s by the British Film Institute. Cooper received several awards including the ‘Academy Award,’ ‘Golden globe Award,’ ‘National Board of Review Award,’ and ‘Broadcast Film Critics Association Award’ for his performance in the film. He was next seen in films like ‘Seabiscuit’ (2003), ‘Silver City’ (2004), ‘Capote’ (2005), ‘Breach’ (2007), ‘New York, I Love You’ (2009), ‘The Company Men’ (2010), ‘Remember Me’ (2010), ‘The Town’ (2010), and ‘The Muppets’ (2011).
In 2013, he was seen playing the role of ‘Charles Aiken’ in the American tragicomedy film ‘August: Osage County’ directed by John Wells. The film received a mixed response from critics and did decent business at the box office. He next appeared in films like ‘The Amazing Spider-Man 2’ (2014), ‘Demolition’ (2015), ‘Live by Night’ (2016), ‘Cars 3’ (2017), ‘Little Women’ (2019), and ‘Irresistible’ (2020). He was last seen in the 2022 documentary film ‘True Value’ directed by Alexander Freeman. Cooper will be next seen in the upcoming American drama film ‘Boston Strangler’ directed by Matt Ruskin.