Pierson's first feature screenplay as co-writer was for "Cat Ballou" (1965) which earned him an Oscar nomination, and he won the award for his finely observed solo script for Sidney Lumet's "Dog Day Afternoon" (1975). Other collaborations includes the classic individual-against-the-unjust-prison-system drama, "Cool Hand Luke" (1967, which also netted him an Oscar nod), as well as adaptations of Scott Turow's bestseller "Presumed Innocent" (1990) and Bobbie Ann Mason's novel "In Country" (1989).
Pierson made his feature directorial debut with "The Looking Glass War" (1970) and subsequently helmed the 1976 Barbra Streisand-Kris Kristofferson remake of "A Star Is Born" as well as "King of the Gypsies" (1978), all of which he also scripted.
In the 90s, Pierson found a home on the small screen, helming a series of well-reviewed, award-winning cable films ranging from biopics (1992's "Citizen Cohn" and 1995's "Truman", both for HBO) as well the First Amendment drama "Dirty Pictures" (Showtime, 2000). In 2001, he earned acclaim for "Conspiracy" (HBO), the talky but highly dramatic re-enactment of the secret Wannsee meeting that led to the Nazi plan for the extermination of all Jews in Europe. Later that year, Pierson was elected president of the Academy of Motion Picture Arts and Sciences, a position he held for the maximum four consecutive terms.